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Journal articles on the topic 'Indoles'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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1

Sharma, Upendra, Inder Kumar, and Rakesh Kumar. "Recent Advances in the Regioselective Synthesis of Indoles via C–H Activation/Functionalization." Synthesis 50, no. 14 (May 28, 2018): 2655–77. http://dx.doi.org/10.1055/s-0037-1609733.

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Indole is an important heterocyclic motif that occurs ubiquitously in bioactive natural products and pharmaceuticals. Immense efforts have been devoted to the synthesis of indoles starting from the Fisher indole synthesis to the recently developed C–H activation/functionalization-based methods. Herein, we have reviewed the progress made on the regioselective synthesis of functionalized indoles, including 2-substituted, 3-substituted and 2,3-disusbstituted indoles, since the year 2010.1 Introduction2 Metal-Catalyzed Synthesis of 2-Substituted Indoles3 Metal-Catalyzed Synthesis of 3-Substituted Indoles4 Metal-Free Synthesis of 3-Substituted Indoles5 Metal-Catalyzed 2,3-Disubstituted Indole Synthesis5.1 Metal-Catalyzed Intramolecular 2,3-Disubstituted Indole Synthesis5.2 Metal-Catalyzed Intermolecular 2,3-Disubstituted Indole Synthesis6 Metal-Free 2,3-Disubstituted Indole Synthesis6.1 N-Protected 2,3-Disubstituted Indole Synthesis6.2 N-Unprotected 2,3-Disubstituted Indole Synthesis7 Applications8 Summary and Outlook

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2

Vincent, Guillaume, Hussein Abou-Hamdan, and Cyrille Kouklovsky. "Dearomatization Reactions of Indoles to Access 3D Indoline Structures." Synlett 31, no. 18 (June 24, 2020): 1775–88. http://dx.doi.org/10.1055/s-0040-1707152.

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This Account summarizes our involvement in the development of dearomatization reactions of indoles that has for origin a total synthesis problematic. We present the effort from our group to obtain 3D-indolines scaffold from the umpolung of N-acyl indoles via activation with FeCl3 to the oxidative spirocyclizations of N-EWG indoles and via the use of electrochemistry.1 Introduction2 Activation of N-Acyl Indoles with FeCl3 2.1 Hydroarylation of N-Acyl Indoles2.2 Difunctionalization of N-Acyl Indoles3 Radical-Mediated Dearomatization of Indoles for the Synthesis of Spirocyclic Indolines4 Electrochemical Dearomatization of Indoles4.1 Direct Electrochemical Oxidation of Indoles4.2 Indirect Electrochemical Oxidation of Indoles5 Conclusion

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3

Kumar, Anil, and Ganesh Shelke. "Sc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles." Synthesis 49, no. 18 (August 1, 2017): 4321–26. http://dx.doi.org/10.1055/s-0036-1588181.

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Oligomerization of substituted indoles and N-methylindoles was investigated in the presence of catalytic amounts of scandium triflate in dichloromethane. Two types of indole oligomer, 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles were obtained based on the substituent on indole ring. This study constitutes the first example of Sc(OTf)3-catalyzed oligomerization of indoles and gave good yield of 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles.

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4

Trubitsõn, Dmitri, and Tõnis Kanger. "Enantioselective Catalytic Synthesis of N-alkylated Indoles." Symmetry 12, no. 7 (July 17, 2020): 1184. http://dx.doi.org/10.3390/sym12071184.

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During the past two decades, the interest in new methodologies for the synthesis of chiral N-functionalized indoles has grown rapidly. The review illustrates efficient applications of organocatalytic and organometallic strategies for the construction of chiral α-N-branched indoles. Both the direct functionalization of the indole core and indirect methods based on asymmetric N-alkylation of indolines, isatins and 4,7-dihydroindoles are discussed.

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5

Fang, Xinxin, Shang Gao, Zijun Wu, Hequan Yao, and Aijun Lin. "Pd(ii)-Catalyzed oxidative dearomatization of indoles: substrate-controlled synthesis of indolines and indolones." Organic Chemistry Frontiers 4, no. 2 (2017): 292–96. http://dx.doi.org/10.1039/c6qo00698a.

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6

Li, Jiao, and Chun-Lin Zhuang. "Natural Indole Alkaloids from Marine Fungi: Chemical Diversity and Biological Activities." Pharmaceutical Fronts 03, no. 04 (December 2021): e139-e163. http://dx.doi.org/10.1055/s-0041-1740050.

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The indole scaffold is one of the most important heterocyclic ring systems for pharmaceutical development, and serves as an active moiety in several clinical drugs. Fungi derived from marine origin are more liable to produce novel indole-containing natural products due to their extreme living environments. The indole alkaloids from marine fungi have drawn considerable attention for their unique chemical structures and significant biological activities. This review attempts to provide a summary of the structural diversity of marine fungal indole alkaloids including prenylated indoles, diketopiperazine indoles, bisindoles or trisindoles, quinazoline-containing indoles, indole-diterpenoids, and other indoles, as well as their known biological activities, mainly focusing on cytotoxic, kinase inhibitory, antiinflammatory, antimicrobial, anti-insecticidal, and brine shrimp lethal effects. A total of 306 indole alkaloids from marine fungi have been summarized, covering the references published from 1995 to early 2021, expecting to be beneficial for drug discovery in the future.

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7

Ashram, Muhammad, Ahmed Al-Mustafa, Wael A. Al-Zereini, Firas F. Awwadi, and Islam Ashram. "A convenient one-pot approach to the synthesis of novel pyrazino[1,2-a]indoles fused to heterocyclic systems and evaluation of their biological activity as acetylcholinesterase inhibitors." Zeitschrift für Naturforschung B 76, no. 5 (May 1, 2021): 303–12. http://dx.doi.org/10.1515/znb-2020-0205.

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Abstract Pyrazino[1,2-a]indoles fused with various heterocycles, such as oxazolidine, oxazinane, imidazolidine, hexahydropyrimidine and benzimidazole, were synthesized transition metal-free by domino reactions which involved the condensation of 1-(2-bromoethyl)-3-chloro-1H-indole-2-carbaldehydes 28–31 with various nucleophilic amines, resulting in the formation of two new interesting fused heterocycles. The anticholinesterase, antioxidant and antibacterial activities of the compounds were evaluated. Acetylcholinesterase (AChE) inhibitory activities were tested by Ellman’s assay, antioxidant activities were detected using the 2,2-azinobis[3-ethylbenzthiazoline]-6-sulfonic acid (ABTS•+) free-radical scavenging method and antibacterial activities were determined by agar diffusion tests. The oxazolo-pyrazino[1,2-a]indoles (8, 10), the oxazino-pyrazino[1,2-a]indoles (16, 18, 19), the pyrimido-pyrazino[1,2-a]indole (22), and the benzoimidazo-pyrazino[1,2-a]indole (27) possessed the highest inhibitory activity against AChE with IC50 values in the range 20–40 μg mL−1. The oxazolo-pyrazino[1,2-a]indoles (8, 9), the imidazo-pyrazino[1,2-a]indoles (12, 13), and the benzoimidazo-pyrazino[1,2-a]indole (24) revealed the highest antioxidant values with IC50 values less than 300 μg mL−1. However, the oxazolo-pyrazino[1,2-a]indole (11) and imidazo-pyrazino[1,2-a]indoles (12, 13) exhibited weak to moderate bioactivities against all tested Gram-positive bacteria, namely Staphylococcus aureus, Bacillus subtilis and Bacillus cereus.

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8

Yan, Jianwei, Guangjie He, Fulin Yan, Jixia Zhang, and Guisheng Zhang. "The dicarbonylation of indoles via Friedel–Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination." RSC Advances 6, no. 50 (2016): 44029–33. http://dx.doi.org/10.1039/c6ra04016k.

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The reaction of indole and β-carbonyl nitrile to generate dicarbonyl indoles has been developed. This process involves α-oxonation of the β-carbonyl nitrile, Friedel–Crafts reaction with indoles and retro-cyanohydrination form dicarbonyl indoles.

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9

Sharapov, Ainur D., Ramil F. Fatykhov, Igor A. Khalymbadzha, Maria I. Valieva, Igor L. Nikonov, Olga S. Taniya, Dmitry S. Kopchuk, et al. "Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles." Molecules 27, no. 24 (December 13, 2022): 8867. http://dx.doi.org/10.3390/molecules27248867.

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This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-f]indole, pyrano[2,3-g]indole, pyrano[2,3-f]indole, and pyrano[2,3-e]indole and photophysical studies in this series. The synthesis of pyrano[3,2-f], [2,3-g], and [2,3-e]indoles involve a tandem of Bischler–Möhlau reaction of 3-aminophenol with benzoin to form 6-hydroxy- or 4-hydroxyindole followed by Pechmann condensation of these hydroxyindoles with β-ketoesters. Pyrano[2,3-f]indoles were synthesized through the Nenitzescu reaction of p-benzoquinone and ethyl aminocrotonates and subsequent Pechmann condensation of the obtained 5-hydroxyindole derivatives. Among the pyranoindoles studied, the most promising were pyrano[3,2-f] and [2,3-g]indoles. These compounds were characterized by moderate to high quantum yields (30–89%) and a large (9000–15,000 cm−1) Stokes shift. More detailed photophysical studies were carried out for a series of the most promising derivatives of pyrano[3,2-f] and [2,3-g]indoles to demonstrate their positive solvatochromism, and the data collected was analyzed using Lippert-Mataga equation. Quantum chemical calculations were performed to deepen the knowledge of the absorption and emission properties of pyrano[3,2-f] and [2,3-g]indoles as well as to explain their unusual geometries and electronic structures.

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10

Hazra, Somjit, Biplab Mondal, Rajendra Narayan De, and Brindaban Roy. "Pd-catalyzed dehydrogenative C–H activation of iminyl hydrogen with the indole C3–H and C2–H bond: an elegant synthesis of indeno[1,2-b]indoles and indolo[1,2-a]indoles." RSC Advances 5, no. 29 (2015): 22480–89. http://dx.doi.org/10.1039/c4ra16661b.

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11

Das, Jonali, and Sajal Kumar Das. "Regioselectivity of the S_EAr-based cyclizations and S_EAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles." Beilstein Journal of Organic Chemistry 18 (March 8, 2022): 293–302. http://dx.doi.org/10.3762/bjoc.18.33.

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Indole-3,4- and 4,5-fused carbo- and heterocycles are ubiquitous in bioactive natural products and pharmaceuticals, and hence, a variety of synthetic approaches toward such compounds have been developed. Among these, cyclization and annulation of 3,5-unsubstituted, 4-substituted indoles involving an electrophilic aromatic substitution (SEAr) as the ring closure are particularly attractive, because they avoid the use of 3,4- or 4,5-difunctionalized indoles as starting materials. However, since 3,5-unsubstituted, 4-substituted indoles have two potential ring-closure sites (indole C3 and C5 positions), such reactions in principle can furnish either or both of the indole 3,4- and 4,5-fused ring systems. This Commentary will briefly highlight the issue by summarizing recent relevant literature reports.

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12

Zeng, Ming, Jiaqi Chen, Fengye Li, Haojie Li, Lan Zhao, Dengzhao Jiang, Jun Dai, and Wenbo Liu. "Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation." Molecules 28, no. 9 (April 24, 2023): 3676. http://dx.doi.org/10.3390/molecules28093676.

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1,3,5 triazines, especially indole functionalized triazine derivatives, exhibit excellent activities, such as anti-tumor, antibacterial, and anti-inflammatory activities. Traditional methods for the synthesis of N-(2-triazine) indoles suffer from unstable materials and tedious operations. Transition-metal-catalyzed C-C/C-N coupling provides a powerful protocol for the synthesis of indoles by the C-H activation strategy. Here, we report the efficient ruthenium-catalyzed oxidative synthesis of N-(2-triazine) indoles by C-H activation from alkynes and various substituted triazine derivatives in a moderate to good yield, and all of the N-(2-triazine) indoles were characterized by 1H NMR, 13C NMR, and HRMS. This protocol can apply to the gram-scale synthesis of the N-(2-triazine) indole in a moderate yield. Moreover, the reaction is proposed to be performed via a six-membered ruthenacycle (II) intermediate, which suggests that the triazine ring could offer chelation assistance for the formation of N-(2-triazine) indoles.

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13

Tanaka, Yosuke, Takumi Ikeda, Yasuhiro Nachi, Taisei Mizuno, Kousuke Maeda, Chisato Sakamoto, Mugen Yamawaki, Toshio Morita, and Yasuharu Yoshimi. "Transition-Metal-Free Access to 2-Subsituted Indolines from Indoles via Dearomative Nucleophilic Addition Using Two-Molecule Organic Photoredox Catalysts." Photochem 1, no. 3 (November 1, 2021): 448–57. http://dx.doi.org/10.3390/photochem1030027.

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A Photoinduced dearomative nucleophilic addition to N-Boc indoles mediated by two-molecule organic photoredox catalysts such as phenanthrene and 1,4-dicyanobenzene with UV irradiation furnished 2-substituted indolines in moderate to quantitative yields. Hydroxide, alkoxide, and cyanide ions can be used as a nucleophile to provide 2-hydroxy, 2-alkoxy, and 2-cyanoindolines, respectively. Both electron-rich and -deficient indoles, including tryptophan derivatives, can be employed in the photoreaction to provide various indolines. This method provides transition-metal-free access to 2-subsituted indolines from indoles using organic photoredox catalysts under mild conditions.

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14

Zhu, Haoran, Sen Zhao, Yu Zhou, Chunpu Li, and Hong Liu. "Ruthenium-Catalyzed C–H Activations for the Synthesis of Indole Derivatives." Catalysts 10, no. 11 (October 29, 2020): 1253. http://dx.doi.org/10.3390/catal10111253.

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The synthesis of substituted indoles has received great attention in the field of organic synthesis methodology. C–H activation makes it possible to obtain a variety of designed indole derivatives in mild conditions. Ruthenium catalyst, as one of the most significant transition-metal catalysts, has been contributing in the synthesis of indole scaffolds through C–H activation and C–H activation on indoles. Herein, we attempt to present an overview about the construction strategies of indole scaffold and site-specific modifications for indole scaffold via ruthenium-catalyzed C–H activations in recent years.

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15

Wu, Shang, Quanlu Yang, Qinzheng Hu, Yanbin Wang, Lihua Chen, Hong Zhang, Lan Wu, and Jia Li. "Manganese-catalyzed direct C2-allylation of indoles." Organic Chemistry Frontiers 5, no. 19 (2018): 2852–55. http://dx.doi.org/10.1039/c8qo00674a.

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Development of manganese-catalyzed synthesis of functionalized indoles is reported. This method involves direct C–H activation and allylation of indoles with broad substrate tolerance, leading to a series of C2-allylated indole derivatives under mild reaction conditions.

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16

Sun, Haoyi, Kangping Sun, and Jingyong Sun. "Recent Advances of Marine Natural Indole Products in Chemical and Biological Aspects." Molecules 28, no. 5 (February 27, 2023): 2204. http://dx.doi.org/10.3390/molecules28052204.

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The ocean has always been one of the important sources of natural products. In recent years, many natural products with different structures and biological activities have been obtained, and their value has been clearly recognized. Researchers have been deeply engaged in the field of separation and extraction, derivative synthesis, structural studies, biological evaluation, and other fields of research for marine natural products. Thus, a series of marine indole natural products which have structural and biological prospect have caught our eyes. In this review, we summarize some of these marine indole natural products with relatively good pharmacological activity and research value, and discuss issues concerning chemistry, pharmacological activity, biological evaluation, and synthesis, including monomeric indoles, indole peptides, bis-indoles, and annelated indoles. Most of the compounds have cytotoxic, antiviral, antifungal, or anti-inflammatory activities.

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17

Powell, Domonica N., Alyson Swimm, Robert Sonowal, Alexis Bretin, Andrew T. Gewirtz, Rheinallt M. Jones, and Daniel Kalman. "Indoles from the commensal microbiota act via the AHR and IL-10 to tune the cellular composition of the colonic epithelium during aging." Proceedings of the National Academy of Sciences 117, no. 35 (August 17, 2020): 21519–26. http://dx.doi.org/10.1073/pnas.2003004117.

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The intestinal epithelium is a highly dynamic structure that rejuvenates in response to acute stressors and can undergo alterations in cellular composition as animals age. The microbiota, acting via secreted factors related to indole, appear to regulate the sensitivity of the epithelium to stressors and promote epithelial repair via IL-22 and type I IFN signaling. As animals age, the cellular composition of the intestinal epithelium changes, resulting in a decreased proportion of goblet cells in the colon. We show that colonization of young or geriatric mice with bacteria that secrete indoles and various derivatives or administration of the indole derivative indole-3 aldehyde increases proliferation of epithelial cells and promotes goblet cell differentiation, reversing an effect of aging. To induce goblet cell differentiation, indole acts via the xenobiotic aryl hydrocarbon receptor to increase expression of the cytokine IL-10. However, the effects of indoles on goblet cells do not depend on type I IFN or on IL-22 signaling, pathways responsible for protection against acute stressors. Thus, indoles derived from the commensal microbiota regulate intestinal homeostasis, especially during aging, via mechanisms distinct from those used during responses to acute stressors. Indoles may have utility as an intervention to limit the decline of barrier integrity and the resulting systemic inflammation that occurs with aging.

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18

Sarkar, Deeptanu, Andleeb Amin, Tanzeela Qadir, and Praveen K. Sharma. "Synthesis of Medicinally Important Indole Derivatives: A Review." Open Medicinal Chemistry Journal 15, no. 1 (September 30, 2021): 1–16. http://dx.doi.org/10.2174/1874104502015010001.

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Indoles constitute a widely occurring functional group in nature and are present in an extensive number of bioactive natural products and medicinally important compounds. As a result, exponential increases in the development of novel methods for the formation of indole core along with site-specific indoles have been established. Conventional methods for the synthesis of indoles are getting replaced with green methods involving ionic liquids, water as a solvent, solid acid catalyst, microwave irradiation and the use of nanoparticles under solvent-free conditions. In addition, there are immense applications of the substituted indoles in diverse fields.

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19

Gribble, G. W. "Novel chemistry of indole in the synthesis of heterocycles." Pure and Applied Chemistry 75, no. 10 (January 1, 2003): 1417–32. http://dx.doi.org/10.1351/pac200375101417.

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Indoles that are substituted at the 2- or 3-position with electron-withdrawing groups (nitro, phenylsulfonyl) undergo nucleophilic addition, 1,3-dipolar cycloaddition, and Diels–Alder reactions to give a variety of indoles, pyrroloindoles, and carbazoles. New methods for the synthesis of furo[3,4-b]indoles and the novel ring system furo[3,4-b]pyrrole are described for the first time. Diels–Alder reactions of furo[3,4-b]pyrroles afford indoles after dehydration of the primary cycloadducts. Efficient syntheses of both 2- and 3-nitroindoles from indole are reported, and the first generation and successful electrophilic trapping of a 2,3-dilithioindole has been achieved.

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20

Yan, Xue, Ying-De Tang, Cheng-Shi Jiang, Xigong Liu, and Hua Zhang. "Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones." Molecules 25, no. 2 (January 20, 2020): 419. http://dx.doi.org/10.3390/molecules25020419.

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The oxidative, dearomative cross-dehydrogenative coupling of indoles with various C-H nucleophiles is developed. This process features a broad substrate scope with respect to both indoles and nucleophiles, affording structurally diverse 2,2-disubstituted indolin-3-ones in high yields (up to 99%). The oxidative dimerization and trimerization of indoles has also been demonstrated under the same conditions.

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21

Haak, Edgar. "Modern Annulation Strategies for the Synthesis of Cyclo[b]fused Indoles." Synlett 30, no. 03 (December 13, 2018): 245–51. http://dx.doi.org/10.1055/s-0037-1610336.

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2,3-Annulated indoles exhibit a broad spectrum of biological activities. Various annulation strategies are applied to generate these scaffolds from prefunctionalized aniline or indole derivatives. Only a few methodologies allow the direct annulation of indole itself, often associated with regioselectivity issues or restrictions on available substitution patterns. More recently, ruthenium-catalyzed cascade transformations of readily available propargyl alcohols have been applied to the selective synthesis of various cyclo[b]fused indoles directly from indole. These efficient processes provide rapid access to intricate molecular structures from simple starting materials and facilitate the preparation of drug-like molecules.

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22

Abdel-Hay, Karim M., Tarek S. Belal, Younis Abiedalla, Amber Thaxton-Weissenfluh, Jack DeRuiter, Forrest Smith, and C. Randall Clark. "Gas Chromatography–Mass Spectrometry (GC–MS) and Gas Chromatography–Infrared (GC–IR) Analyses of the Chloro-1-n-pentyl-3-(1-naphthoyl)-Indoles: Regioisomeric Cannabinoids." Applied Spectroscopy 73, no. 4 (November 16, 2018): 433–43. http://dx.doi.org/10.1177/0003702818809998.

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The analytical differentiation of the indole ring regioisomeric chloro-1- n-pentyl-3-(1-naphthoyl)-indoles is described in this report. The regioisomeric chloroindole precursor compounds, N- n-pentyl chloroindole synthetic intermediates, and the target chloro-substituted naphthoylindoles showed the equivalent gas chromatographic elution order based on the position of chlorine substitution on the indole ring. The regioisomeric chloro-1- n-pentyl-3-(1-naphthoyl)-indoles yield electron ionization mass spectra having equivalent major fragments resulting from cleavage of the groups attached to the central indole nucleus. Fragment ions occur at m/z 127 and 155 for the naphthyl and naphthoyl cations common to all indoles having the naphthoyl group substituted at the indole-3 position. Fragments resulting from the loss of the naphthoyl and/or n-pentyl groups from the molecular radical cation yield the cations at m/z 318, 304, 248, and 178. The characteristic (M–17)+ fragment ion at m/z 358 resulting from the loss of OH radical is significant in the mass spectra of all these compounds with 1-naphthoyl groups substituted at the indole-3 position. The vapor phase infrared spectra provide a number of characteristic absorption bands to identify the individual isomers.

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23

Zhang, Yan, Zhe-Yao Hu, Xin-Chang Li, and Xun-Xiang Guo. "Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids." Synthesis 51, no. 08 (January 10, 2019): 1803–8. http://dx.doi.org/10.1055/s-0037-1611946.

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A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles in high yields. This synthetic method shows good functional group tolerance and offers an alternative route to construct N-aryl indoles.

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24

Zgarbová, Eliška, and Radim Vrzal. "The Impact of Indoles Activating the Aryl Hydrocarbon Receptor on Androgen Receptor Activity in the 22Rv1 Prostate Cancer Cell Line." International Journal of Molecular Sciences 24, no. 1 (December 28, 2022): 502. http://dx.doi.org/10.3390/ijms24010502.

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The activation of the aryl hydrocarbon receptor (AhR) by xenobiotic compounds was demonstrated to result in the degradation of the androgen receptor (AR). Since prostate cancer is often dependent on AR, it has become a significant therapeutic target. As a result of the emerging concept of bacterial mimicry, we tested whether compounds with indole scaffolds capable of AhR activation have the potential to restrict AR activity in prostate cancer cells. Altogether, 22 indolic compounds were tested, and all of them activated AhR. However, only eight decreased DHT-induced AR luciferase activity. All indoles, which met the AhR-activating and AR-suppressing criteria, decreased the expression of DHT-inducible AR target genes, specifically KLK3 and FKBP5 mRNAs. The reduced AR binding to the KLK3 promoter was confirmed by a chromatin immunoprecipitation (ChIP) assay. In addition, some indoles significantly decreased AR protein and mRNA level. By using CRISPR/Cas9 AhR knockout technology, no relationship between AhR and AR, measured as target gene expression, was observed. In conclusion, some indoles that activate AhR possess AR-inhibiting activity, which seems to be related to the downregulation of AR expression rather than to AR degradation alone. Moreover, there does not seem to be a clear relationship that would connect AhR activation with AR activity suppression in 22Rv1 cells.

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25

Singh, Anoop, Satheeshvarma Vanaparthi, Sachin Choudhary, Rangan Krishnan, and Indresh Kumar. "Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed oxidative dimerization of 2-aryl indoles and cross-addition with indoles." RSC Advances 9, no. 42 (2019): 24050–56. http://dx.doi.org/10.1039/c9ra04741g.

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A general protocol for the synthesis of 2,2-disubstituted indolin-3-ones has been developed through self-dimerization of 2-aryl indoles and cross-addition with indoles under mild Cu-catalyzed oxidative conditions with good to high yields.

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26

Mazzotta, Sarah, Luca Frattaruolo, Matteo Brindisi, Cristina Ulivieri, Francesca Vanni, Antonella Brizzi, Gabriele Carullo, Anna R. Cappello, and Francesca Aiello. "3-Amino-alkylated indoles: unexplored green products acting as anti-inflammatory agents." Future Medicinal Chemistry 12, no. 1 (January 2020): 5–17. http://dx.doi.org/10.4155/fmc-2019-0234.

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Aim: Over the years, indole has proved to be a versatile scaffold for the design of molecules acting as anti-inflammatory agents. Materials & Methods: A small library of 3-amino-alkylated indoles has been obtained by an optimized Mannich green approach. The anti-inflammatory activity of the new 3-amino-alkylated indoles, GLYC 0–10, was evaluated in RAW 264.7 macrophages. Results: The anti-inflammatory activity of the new 3-amino-alkylated indoles, GLYC 0–10, was evaluatedn and, among them, GLYC 4, 5 and 9 displayed the greatest inhibitory effects on nitric oxide production, with IC50 values of 5.41, 4.22 and 6.3 μM, respectively. Conclusion: Our outcomes, overall, highlight the importance of the indole substitution in the anti-inflammatory activity of these compounds, exerted by acting on the interlinked NF-κB/ERK1/2 pathways.

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27

Fang, Shu-Yen, Sheng-Yuan Chen, You-Ying Chen, Tsu-Jen Kuo, Zhi-Hong Wen, Yu-Hsin Chen, Tsong-Long Hwang, and Ping-Jyun Sung. "Natural Indoles From the Bacterium Pseudovibrio denitrificans P81 Isolated From a Marine Sponge, Aaptos Species." Natural Product Communications 16, no. 9 (September 2021): 1934578X2110337. http://dx.doi.org/10.1177/1934578x211033735.

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A new natural indole, vibrindole B (1), together with known analogs, vibrindole A (2), trisindoline (3), norharmane (4), and 3-(hydroxyacetyl)indole (5), produced by the bacterium Pseudovibrio denitrificans P81, were isolated from a sponge, Aaptos species. The structures of indoles 1 to 5 were established by spectroscopic methods. The proposed biosynthetic pathway of 1 to 5 is also discussed, starting from tryptophan. Moreover, indoles 1 to 3 were found to exhibit cytotoxicity toward T24 tumor cells with IC50 values of 1.71 ± 0.11, 4.53 ± 0.14, and 2.26 ± 0.26 µM, respectively.

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Chen, Xiao Yun, Yaonan Tang, Xinran Xiang, Yisong Tang, Mingyang Huang, Shaojun Zheng, and Cuifeng Yang. "Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-Dibromo Indoles Using N-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents." Molecules 28, no. 8 (April 11, 2023): 3380. http://dx.doi.org/10.3390/molecules28083380.

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A green one-pot 2,3,6-trifunctionalization of N-alkyl/aryl indoles was achieved by adding three equivalents of N-Br sulfoximine to the indole solution. A variety of 2-sulfoximidoyl-3,6-dibromo indoles were prepared with 38–94% yields using N-Br sulfoximines as both brominating and sulfoximinating reagents. Based on the results of controlled experiments, we propose that a radical substitution involving 3,6-dibromination and 2-sulfoximination occurs in the reaction process. This is first time that 2,3,6-trifunctionalization of indole in one pot has been achieved.

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29

Sarath Chand, S., B. S. Sasidhar, Praveen Prakash, P. Sasikumar, P. Preethanuj, Florian Jaroschik, Dominique Harakat, Jean-Luc Vasse, and K. V. Radhakrishnan. "Lewis acid catalyzed C-3 alkylidenecyclopentenylation of indoles: an easy access to functionalized indoles and bisindoles." RSC Advances 5, no. 48 (2015): 38075–84. http://dx.doi.org/10.1039/c5ra01107h.

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A Lewis acid catalyzed C-3 alkylidenecyclopentenylation of indoles through the ring opening of pentafulvene derived diazabicyclic olefins has been developed toward the synthesis of indole and bisindole derivatives.

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30

Shen, Yang, Zi-Qi Zhu, Jin-Xi Liu, Lei Yu, Bai-Xiang Du, Guang-Jian Mei, and Feng Shi. "Brønsted Acid Catalyzed C3-Alkylation of 2-Indolylmethanols with Azlactones via an Umpolung Strategy." Synthesis 49, no. 17 (June 20, 2017): 4025–34. http://dx.doi.org/10.1055/s-0036-1589036.

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An efficient method for the synthesis of C3-alkylated indoles has been established via Brønsted acid catalyzed alkylation of 2-indolylmethanols with azlactones. The reaction exhibits broad substrate scope and delivers high yields (22 examples, up to 99% yield). This approach not only provides a new strategy for the direct synthesis of C3-alkylated indoles, but also represents a rarely reported alkylation between indole motifs and electron-rich synthons at the C3 position. This protocol serves as a good example of the application of the umpolung strategy in the synthesis of C3-alkylated indoles from 2-indolylmethanols.

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31

Fochi, Mariafrancesca, Luca Bernardi, and Lorenzo Caruana. "Enantioselective Approaches to 3,4-Annulated Indoles Using Organocatalytic Domino Reactions." Synlett 28, no. 13 (April 19, 2017): 1530–43. http://dx.doi.org/10.1055/s-0036-1589494.

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Organocatalytic domino reactions of 4-substituted indoles are summarized in this account. Two reactions have been developed, one with enals, activated by secondary amine catalysts via iminium ions, and one with nitroethene, using a phosphoric acid catalyst. Both reactions required solving the challenge posed by the very low nucleophilicity of the indole substrates, which bear an electron-withdrawing Michael acceptor at C4. DFT calculations were used to shed light on the unique reaction pathway followed by the phosphoric acid catalyzed transformation, wherein a bicoordinated nitronic acid intermediate was found to evolve preferentially through an intramolecular nitro-Michael reaction, instead of the common tautomerization pathway. These reactions provide new and efficient entries to 3,4-ring-fused indoles in diastereo- and enantioenriched form. In more detail, the structures obtained feature a 1,3,4,5-tetrahydrobenzo[cd]indole core, which is present in the structural framework of ergot alkaloids. Indeed, the preparation of an intermediate previously used in ergot alkaloid (6,7-secoagroclavine) synthesis was possible from one of the catalytic adducts.1 Introduction2 Reactions of 4-Substituted Indoles with α,β-Unsaturated Aldehydes Catalyzed by Secondary Amines3 Reactions of 4-Substituted Indoles with Nitroethene Catalyzed by Brønsted Acids4 Conclusion

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32

Martínez, Gabriela, Oscar E. Zimerman, and Norman A. García. "The Aerobic Riboflavin-Sensitized Photodecomposition of Tryptophan, Tryptamine and Indole Acetic Acid. Ground-State and Photopromoted Flavin-Indole Interactions." Collection of Czechoslovak Chemical Communications 58, no. 6 (1993): 1299–308. http://dx.doi.org/10.1135/cccc19931299.

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The interaction between riboflavin (RF) and the indole derivatives tryptophan, tryptamine and indole-3-acetic acid at visible light irradiation was studied in water and water/ethanol mixed solvent. Besides a dark indole-RF association, important only at indole concentration higher than 10-3 mol dm-3, a complex picture of competitive reactions operate. Triplet excited RF is quenched by the indoles in concentrations ca 10-4 mol dm-3 (rate constants of the order of 109 mol-1 dm3 s -1) and by dissolved oxygen. Both, singlet molecular oxygen and superoxide anion (in a further reaction step) are produced. As a consequence the rate of indol photodecomposition decreases in order: indole-3-acetic acid > tryptophan >> tryptamine, and the rate of RF autofading suffers an important delay compared with that in the absence of indoles.

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33

Khan, Neyaz A., Navdeep Kaur, Peter Owens, Olivier P. Thomas, and Aoife Boyd. "Bis-Indole Alkaloids Isolated from the Sponge Spongosorites calcicola Disrupt Cell Membranes of MRSA." International Journal of Molecular Sciences 23, no. 4 (February 11, 2022): 1991. http://dx.doi.org/10.3390/ijms23041991.

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Antimicrobial resistance (AMR) is a global health challenge with methicillin resistant Staphylococcus aureus (MRSA), a leading cause of nosocomial infection. In the search for novel antibiotics, marine sponges have become model organisms as they produce diverse bioactive compounds. We investigated and compared the antibacterial potential of 3 bis-indole alkaloids—bromodeoxytopsentin, bromotopsentin and spongotine A—isolated from the Northeastern Atlantic sponge Spongosorites calcicola. Antimicrobial activity was determined by MIC and time-kill assays. The mechanism of action of bis-indoles was assessed using bacterial cytological profiling via fluorescence microscopy. Finally, we investigated the ability of bis-indole alkaloids to decrease the cytotoxicity of pathogens upon co-incubation with HeLa cells through the measurement of mammalian cell lysis. The bis-indoles were bactericidal to clinically relevant Gram-positive pathogens including MRSA and to the Gram-negative gastroenteric pathogen Vibrio parahaemolyticus. Furthermore, the alkaloids were synergistic in combination with conventional antibiotics. Antimicrobial activity of the bis-indole alkaloids was due to rapid disruption and permeabilization of the bacterial cell membrane. Significantly, the bis-indoles reduced pathogen cytotoxicity toward mammalian cells, indicating their ability to prevent bacterial virulence. In conclusion, sponge bis-indole alkaloids are membrane-permeabilizing agents that represent good antibiotic candidates because of their potency against Gram-positive and Gram-negative bacterial pathogens.

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34

Hilgeroth, Andreas, Kaveh Yasrebi, Sibel Suzen, Tobias Hertlein, Knut Ohlsen, and Michael Lalk. "Antibacterial Evaluation of Novel Substituted Cycloheptaindoles in Staphylococcus and Enterococcus Strains." Medicinal Chemistry 15, no. 8 (November 18, 2019): 833–39. http://dx.doi.org/10.2174/1573406415666190208170126.

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Background: Due to emerging resistances against antibiotics there is a strong need to find novel antibacterial agents with a novel structure to prevent early resistance developments. Objective: Bisindole compounds with antibacterial activities which formally result from the reaction of an aldehyde with indole motivated to investigate the reaction of a dialdehyde and indole to give novel structures with potential antibacterial activities. Methods: Compounds were yielded by chemical synthesis and purified using column chromatography. The antibacterial activity was determined as minimal inhibitory growth activity in cultures of Gram-positive strains of Staphylococcus aureus and Enterococcus species. Results: Cyclohepta[2,3-b]indoles have been yielded in a one-step reaction procedure with indole substitutions at the cycloheptane central core matching a solution for achieving fused novel cycloalkane indoles with functionalized residues of promising biological activity. So far fused cycloalkane indoles have not been available in a one-step procedure and moreover, core functionalizations have been additional challenges. Various indole substitutions have been done to provide a first set of compounds. Conclusion: Substituent-dependent effects have been suggested to influence the antibacterial activity and first compounds were identified with specific Staphylococcus activities and Enterococcus species effects towards Enterococcus faecalis as critical pathogens in the hospital with upcoming resistances against standard antibiotics.

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35

Rinderspacher, Alison, and Gordon W. Gribble. "The Generation of Indole-2,3-quinodimethanes from the Deamination of 1,2,3,4-Tetrahydropyrrolo[3,4-b]indoles." Molecules 25, no. 2 (January 9, 2020): 261. http://dx.doi.org/10.3390/molecules25020261.

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36

Bartoli, Giuseppe, Renato Dalpozzo, and Monica Nardi. "Applications of Bartoli indole synthesis." Chem. Soc. Rev. 43, no. 13 (2014): 4728–50. http://dx.doi.org/10.1039/c4cs00045e.

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37

Ni, Penghui, Bin Li, Huawen Huang, Fuhong Xiao, and Guo-Jun Deng. "Solvent-controlled highly regio-selective thieno[2,3-b]indole formation under metal-free conditions." Green Chemistry 19, no. 23 (2017): 5553–58. http://dx.doi.org/10.1039/c7gc02818k.

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38

Liu, Jiarun, Jiancheng Huang, Kuiyong Jia, Tianxing Du, Changyin Zhao, Rongxiu Zhu, and Xigong Liu. "Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones." Synthesis 52, no. 05 (November 28, 2019): 763–68. http://dx.doi.org/10.1055/s-0039-1691528.

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A metal-free oxidative dearomatization of indoles with aromatic ketones mediated by TEMPO oxoammonium salt is described. The dearomatization proceeds smoothly and displays a broad substrate scope with respect to both indoles and aromatic ketones in the presence of H2SO4, affording the corresponding 2,2-disubstituted indolin-3-ones in good yields.

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39

Sun, Wei, William A. T. Raimbach, Luke D. Elliott, Kevin I. Booker-Milburn, and David C. Harrowven. "New approaches to ondansetron and alosetron inspire a versatile, flow photochemical method for indole synthesis." Chemical Communications 58, no. 3 (2022): 383–86. http://dx.doi.org/10.1039/d1cc05700f.

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40

Sanap, Anita Kailas, and Ganapati Subray Shankarling. "Choline chloride based eutectic solvents: direct C-3 alkenylation/alkylation of indoles with 1,3-dicarbonyl compounds." RSC Adv. 4, no. 66 (2014): 34938–43. http://dx.doi.org/10.1039/c4ra05858e.

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41

Padmaja, Pannala, Pedavenkatagari Narayana Reddy, and Bijaya Ketan Sahoo. "A Green Approach to the Synthesis of Novel Indole Substituted 2-Amino- 4,5-dihydro-3-furancarbonitriles in Water." Letters in Organic Chemistry 16, no. 3 (February 11, 2019): 209–14. http://dx.doi.org/10.2174/1570178615666180917104820.

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2-Amino-4,5-dihydro-3-furancarbonitriles (ADFCs) have attracted much attention due to their utility as valuable synthetic intermediates for the preparation of a series of acyclic and cyclic organic compounds. On the other hand, indoles substituted with furans are highly interesting compounds displaying a wide range of biological and pharmaceutical activities. However, to the best of our knowledge, indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles have not been previously reported. A new and efficient synthesis of indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles has been developed in two steps using water as a solvent. The first step of the sequence involves threecomponent reaction of phenylglyoxals, indoles and malononitrile under aqueous and catalyst-free conditions for the synthesis of indole substituted β,β-dicyanoketones. Reduction of the obtained β,β- dicyanoketones with sodium borohydride in water at room temperature afforded the indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles in good yields. Several substituted phenylglyooxals were reacted smoothly with indole or 2-methylindole and malononitrile to give the corresponding indole substituted β,β-dicyanoketones in good yields. Treatment of the obtained β,β-dicyanoketones with sodium borohydride in water furnished exclusively the indole substituted 2-amino-4,5-dihydro-3- furancarbonitriles in good yields. We have developed an efficient straightforward access to indole substituted β,β-dicyanoketones by one-pot three-component reaction of phenylglyoxals, indoles and malononitrile. The synthetic utility of obtained indole substituted β,β-dicyanoketones has been outlined by the preparation of indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles. The advantage of catalyst-free, atom-economical and environmental benignity render it promising methods for preparation of indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles.

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42

Sonowal, Robert, Alyson Swimm, Anusmita Sahoo, Liping Luo, Yohei Matsunaga, Ziqi Wu, Jui A. Bhingarde, et al. "Indoles from commensal bacteria extend healthspan." Proceedings of the National Academy of Sciences 114, no. 36 (August 21, 2017): E7506—E7515. http://dx.doi.org/10.1073/pnas.1706464114.

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Multiple studies have identified conserved genetic pathways and small molecules associated with extension of lifespan in diverse organisms. However, extending lifespan does not result in concomitant extension in healthspan, defined as the proportion of time that an animal remains healthy and free of age-related infirmities. Rather, mutations that extend lifespan often reduce healthspan and increase frailty. The question arises as to whether factors or mechanisms exist that uncouple these processes and extend healthspan and reduce frailty independent of lifespan. We show that indoles from commensal microbiota extend healthspan of diverse organisms, including Caenorhabditis elegans, Drosophila melanogaster, and mice, but have a negligible effect on maximal lifespan. Effects of indoles on healthspan in worms and flies depend upon the aryl hydrocarbon receptor (AHR), a conserved detector of xenobiotic small molecules. In C. elegans, indole induces a gene expression profile in aged animals reminiscent of that seen in the young, but which is distinct from that associated with normal aging. Moreover, in older animals, indole induces genes associated with oogenesis and, accordingly, extends fecundity and reproductive span. Together, these data suggest that small molecules related to indole and derived from commensal microbiota act in diverse phyla via conserved molecular pathways to promote healthy aging. These data raise the possibility of developing therapeutics based on microbiota-derived indole or its derivatives to extend healthspan and reduce frailty in humans.

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43

Aksenov, Nicolai A., Nikolai A. Arutiunov, Igor A. Kurenkov, Vladimir V. Malyuga, Dmitrii A. Aksenov, Daria S. Momotova, Anna M. Zatsepilina, Elizaveta A. Chukanova, Alexander V. Leontiev, and Alexander V. Aksenov. "A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene." Molecules 28, no. 9 (April 23, 2023): 3657. http://dx.doi.org/10.3390/molecules28093657.

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A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-isoxazoles]. The latter could be transformed to corresponding aminated indoles by reaction with hydrazine hydrate in good or excellent yields upon microwave-assisted heating.

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44

Yuan, Hao, Jianxian Gong, and Zhen Yang. "A rhodium-catalyzed tandem reaction of N-sulfonyl triazoles with indoles: access to indole-substituted indanones." Chemical Communications 53, no. 65 (2017): 9089–92. http://dx.doi.org/10.1039/c7cc05139e.

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45

Zhang, Yong-Sheng, Xiang-Ying Tang, and Min Shi. "Divergent synthesis of indole-fused polycycles via Rh(ii)-catalyzed intramolecular [3 + 2] cycloaddition and C–H functionalization of indolyltriazoles." Organic Chemistry Frontiers 2, no. 11 (2015): 1516–20. http://dx.doi.org/10.1039/c5qo00216h.

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46

Zalte, Rajesh R., Alexey A. Festa, Nikita E. Golantsov, Karthikeyan Subramani, Victor B. Rybakov, Alexey V. Varlamov, Rafael Luque, and Leonid G. Voskressensky. "Aza-Henry and aza-Knoevenagel reactions of nitriles for the synthesis of pyrido[1,2-a]indoles." Chemical Communications 56, no. 48 (2020): 6527–30. http://dx.doi.org/10.1039/d0cc01652g.

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47

Bakthadoss, Manickam, Polu Vijay Kumar, Tadiparthi Thirupathi Reddy, and Duddu S. Sharada. "Solvent and catalyst free ring expansion of indoles: a simple synthesis of highly functionalized benzazepines." Organic & Biomolecular Chemistry 16, no. 43 (2018): 8160–68. http://dx.doi.org/10.1039/c8ob01825a.

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48

Eldehna, Wagdy M., Ghada S. Hassan, Sara T. Al-Rashood, Hamad M. Alkahtani, Abdulrahman A. Almehizia, and Ghada H. Al-Ansary. "Marine-Inspired Bis-indoles Possessing Antiproliferative Activity against Breast Cancer; Design, Synthesis, and Biological Evaluation." Marine Drugs 18, no. 4 (April 2, 2020): 190. http://dx.doi.org/10.3390/md18040190.

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Diverse indoles and bis-indoles extracted from marine sources have been identified as promising anticancer leads. Herein, we designed and synthesized novel bis-indole series 7a–f and 9a–h as Topsentin and Nortopsentin analogs. Our design is based on replacing the heterocyclic spacer in the natural leads by a more flexible hydrazide linker while sparing the two peripheral indole rings. All the synthesized bis-indoles were examined for their antiproliferative action against human breast cancer (MCF-7 and MDA-MB-231) cell lines. The most potent congeners 7e and 9a against MCF-7 cells (IC50 = 0.44 ± 0.01 and 1.28 ± 0.04 μM, respectively) induced apoptosis in MCF-7 cells (23.7-, and 16.8-fold increase in the total apoptosis percentage) as evident by the externalization of plasma membrane phosphatidylserine detected by Annexin V-FITC/PI assay. This evidence was supported by the Bax/Bcl-2 ratio augmentation (18.65- and 11.1-fold compared to control) with a concomitant increase in the level of caspase-3 (11.7- and 9.5-fold) and p53 (15.4- and 11.75-fold). Both compounds arrested the cell cycle mainly in the G2/M phase. Furthermore, 7e and 9a displayed good selectivity toward tumor cells (S.I. = 38.7 and 18.3), upon testing of their cytotoxicity toward non-tumorigenic breast MCF-10A cells. Finally, compounds 7a, 7b, 7d, 7e, and 9a were examined for their plausible CDK2 inhibitory action. The obtained results (% inhibition range: 16%–58%) unveiled incompetence of the target bis-indoles to inhibit CDK2 significantly. Collectively, these results suggested that herein reported bis-indoles are good lead compounds for further optimization and development as potential efficient anti-breast cancer drugs.

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Uruvakili, Anasuyamma, and K. C. Kumara Swamy. "Gold catalysed transformation of 2-arylindoles to terphenyl amines via 3-dienyl indoles and Brønsted acid promoted formation of 2-carboxyindoles to 3-indenylindoles via 3-allenylindoles." Organic & Biomolecular Chemistry 17, no. 12 (2019): 3275–84. http://dx.doi.org/10.1039/c9ob00232d.

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Macha, Lingamurthy, Deepak Singh, Hyong-Jin Rhee, and Hyun-Joon Ha. "Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines." Organic & Biomolecular Chemistry 18, no. 46 (2020): 9473–82. http://dx.doi.org/10.1039/d0ob01865a.

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