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Journal articles on the topic 'Indolizine'

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Author: Grafiati

Published: 4 June 2021

Last updated: 4 May 2024

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1

Albota, Florin, Mino R. Caira, Constantin Draghici, Florea Dumitrascu, and Denisa E. Dumitrescu. "Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis." Beilstein Journal of Organic Chemistry 12 (November 23, 2016): 2503–10. http://dx.doi.org/10.3762/bjoc.12.245.

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The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of the new compounds were assigned by FTIR, NMR spectroscopy and X-ray analysis.

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2

Guidotti, Bruno Boni, Thiago Sabino da Silva, José Tiago Menezes Correia, and Fernando Coelho. "Brønsted-acid-catalyzed selective Friedel–Crafts monoalkylation of isatins with indolizines in water." Organic & Biomolecular Chemistry 18, no. 37 (2020): 7330–35. http://dx.doi.org/10.1039/d0ob01714k.

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3

Chan, Siu-Chung, Chi-Fung Yeung, Hau-Lam Shek, Sze-Wing Ng, Sheung-Ying Tse, Man-Kit Tse, Shek-Man Yiu, and Chun-Yuen Wong. "Iron(ii)-induced cycloisomerization of alkynes via “non-vinylidene” pathways for iron(ii)-indolizine and -indolizinone complexes." Chemical Communications 56, no. 83 (2020): 12644–47. http://dx.doi.org/10.1039/d0cc05081d.

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4

Botezatu (Dediu), Andreea Veronica, Georgiana Horincar, Ioana Otilia Ghinea, Bianca Furdui, Gabriela-Elena Bahrim, Vasilica Barbu, Fanica Balanescu, Lidia Favier, and Rodica-Mihaela Dinica. "Whole-Cells of Yarrowia lipolytica Applied in “One Pot” Indolizine Biosynthesis." Catalysts 10, no. 6 (June 5, 2020): 629. http://dx.doi.org/10.3390/catal10060629.

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A series of yeast strains was tested in order to evaluate their catalytic potential in biocatalysis of one-pot indolizine’s synthesis. Yeast cultivation was performed in a submerged system at 28 °C for 72 h at 180 rpm. An assessment of the reagents’ toxicity on yeast viability and metabolic functionality concluded that the growth potential of three Yarrowia lipolytica strains were least affected by the reactants compared to the other yeast strains. Further, crude fermentation products (biomass and cell-free supernatant)—obtained by submerged cultivation of these yeasts—were used in multistep cascade reactions for the production of fluorescent indolizine compounds with important biologic activities. A whole–cell catalyzed multicomponent reaction of activated alkynes, α-bromo-carbonyl reagents and 4,4′-bipyridine, at room temperature in buffer solution led to the efficient synthesis of bis-indolizines 4a, 4b and 4c, in good-to-excellent yields (47%–77%). The metabolites of the selected Y. lipolytica strains can be considered effective biocatalysts in cycloaddition reactions and the high purity and bioconversion yields of the synthesized indolizines indicates a great potential of this type of “green” catalysts. Seeds of Triticum estivum L. were used to investigate the impact of the final products on the germination and seedling growth. The most sensitive physiological parameters suggest that indolizines, at the concentrations tested, have non-toxic effect on germination and seedling growth of wheat, fact also confirmed by confocal laser scanning microscopy images.

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5

Venugopala, Katharigatta N., Sandeep Chandrashekharappa, Subhrajyoti Bhandary, Deepak Chopra, Mohammed A. Khedr, Bandar E. Aldhubiab, Mahesh Attimarad, and Bharti Odhav. "Efficient Synthesis and Characterization of Novel Substituted 3-Benzoylindolizine Analogues via the Cyclization of Aromatic Cycloimmoniumylides with Electrondeficient Alkenes." Current Organic Synthesis 15, no. 3 (April 27, 2018): 388–95. http://dx.doi.org/10.2174/1570179414666171024155051.

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Background: Indolizine pharmacophore is known to exhibit various promising pharmacological properties such as analgesic, anticancer, antihistaminic, antidiabetic, anti-inflammatory, antileishmanic, antimicrobial, antimutagenic, antioxidant, antitubercular, antiviral, larvicidal and herbicidal activities. Objective: In the present investigation, it was envisaged to synthesize a series of novel ethyl-7-substituted-3-(4- substituted benzoyl)-2-substituted indolizine-1-carboxylates by employing chromium(IV)oxide as dehydrogenating agent with triethylamine combination. Method: Synthesis of a series of proposed polysubstituted indolizines by employing chromium(IV)oxide as dehydrogenating agent with triethylamine combination. Final compounds were characterized by spectroscopic techniques viz fourier-transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, liquid chromatography- mass spectrometry, elemental analysis and selected title compound diethyl-3-(4- cyanobenzoyl)indolizine-1,2-dicarboxylate by single crystal X-ray method. Results: Aromatic cycloimmoniumylides undergo smooth cyclization with electron-deficient alkenes in the presence of triethylamine and DMF at room temperature to afford intermediates ethyl 7-substituted-2- substituted-3-(4-substituted benzoyl)-1,2,3,8a-tetrahydroindolizine-1-carboxylates, which on dehydrogenation with chromium(IV)oxide to obtain the title compounds ethyl-7-substituted-3-(4-substituted benzoyl)-2- substituted indolizine-1-carboxylates. Conclusion: The research was focused on developing an efficient protocol for the synthesis of a novel series of ethyl 3-substituted benzoyl-7-substituted-2-substituted indolizine-1-carboxylates with suitable pharmacological properties in good to excellent yields.

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6

Ma, Lanchao, Bing Chen, Yunlong Guo, Yongri Liang, Dongmei Zeng, Xiaowei Zhan, Yunqi Liu, and Xingguo Chen. "NIR polymers and phototransistors." Journal of Materials Chemistry C 6, no. 47 (2018): 13049–58. http://dx.doi.org/10.1039/c8tc03917h.

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A novel bisthiophene-fused diketopyrrolopyrrole unit (4,11-bis(2-octyldodecyl)-7H,14H-thieno[3′,2′:7,8]indolizino[2,1-a]thieno[3,2-g]indolizine-7,14-dione, BTI) has been designed as an electron acceptor and used to copolymerize with thiophene and bithiophene as electron donors to construct two D–A conjugated polymers, P1 and P2via Stille coupling, respectively.

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7

Chudík, Miloslav, Štefan Marchalín, and Katarína Havrilová. "Synthesis and Spectral Properties of Methyl 6-Acetyl- or 6-Cyano-3-amino-2-benzoyl-7-furyl-5-methylindolizine-8-carboxylates." Collection of Czechoslovak Chemical Communications 63, no. 6 (1998): 826–34. http://dx.doi.org/10.1135/cccc19980826.

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Good yields of methyl 6-acetyl- or 6-cyano-3-amino-2-benzoyl-5-methyl-7-(5-substituted-2-furyl)indolizine-8-carboxylates (5a-5f) were obtained in the reaction of corresponding 5-acetyl- or 5-cyano-2-formyl-4-(5-substituted-2-furyl)-6-methyl-1,4-dihydropyridine-3-carboxylated (4a-4f) with 3-phenyl-3-oxopropanenitrile. Spectral properties of the indolizines 5 are discussed.

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8

Venugopala, Katharigatta N., Christophe Tratrat, Melendhran Pillay, Fawzi M. Mahomoodally, Subhrajyoti Bhandary, Deepak Chopra, Mohamed A. Morsy, et al. "Anti-Tubercular Activity of Substituted 7-Methyl and 7-Formylindolizines and In Silico Study for Prospective Molecular Target Identification." Antibiotics 8, no. 4 (December 3, 2019): 247. http://dx.doi.org/10.3390/antibiotics8040247.

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Novel series of diversely substituted indolizines were designed, synthesized, and evaluated for their in vitro anti-mycobacterial activity against H37Rv and multi-drug-resistant (MDR) strains of Mycobacterium tuberculosis (MTB). Many compounds exhibited significant inhibitory activity against MTB H37Rv strains. Indolizines 2d, 2e, and 4 were also found to be active against MTB clinical isolates with multi-resistance to rifampicin and isoniazid. Indolizine 4 was identified as the most promising anti-mycobacterial agent, displaying minimum inhibitory concentration (MIC) values of 4 and 32 μg/mL against H37Rv and MDR strains, respectively. Furthermore, an in silico study was carried out for prospective molecular target identification and revealed favorable interactions with the target enzymes CYP 121, malate synthase, and DNA GyrB ATPase. None of the potent molecules presented toxicity against peripheral blood mononuclear (PBM) cell lines, demonstrating their potentiality to be used for drug-sensitive and drug-resistant tuberculosis therapy.

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9

Matsumoto, Kiyoshi, Yukio Ikemi, Motoo Shiro, Takane Uchida, and James William Lown. "Reactions of 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizines with dimethyl acetylenedicarboxylate: regioselective formation of 1:2 Michael type adducts." Canadian Journal of Chemistry 71, no. 4 (April 1, 1993): 529–33. http://dx.doi.org/10.1139/v93-075.

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Reactions of 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizines with dimethyl acetylenedicarboxylate afforded the 1:2 adducts regioselectively and, unexpectedly, in a Michael fashion rather than in a 1,3-dipolar manner. The structure of the products was established by X-ray crystallography. Regiospecific formation of the observed product 3 can be explained by the higher nucleophilicity of the nitrogen at the 2 position than at the 3 position of the 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizine 1 owing to the contribution of a resonance structure 5 to the hybrid. This favors two successive Michael additions to two equivalents of dimethyl acetylenedicarboxylate affording the observed 1:2 adducts 3.

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10

Kim, Sunmi, Jeong Hwa Lee, Seok Hyun Yoon, and Ikyon Kim. "A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles: generation of poly-substituted pyridines." Organic & Biomolecular Chemistry 19, no. 26 (2021): 5806–17. http://dx.doi.org/10.1039/d1ob00788b.

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A highly efficient [4 + 2] annulation approach to poly-functionalized indolizine-7-carbonitriles enables us to install nitrile, (hetero)aryl/alkyl, and acyl groups regioselectively on the pyridine unit of indolizine.

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11

Sekgota, Khethobole C., Michelle Isaacs, Heinrich C. Hoppe, Ronnett Seldon, Digby F. Warner, Setshaba D. Khanye, and Perry T. Kaye. "Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids." Journal of Chemical Research 45, no. 7-8 (March 24, 2021): 674–78. http://dx.doi.org/10.1177/1747519820987156.

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Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

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12

Kim, Taegwan, and Jonghoon Kim. "Color-Tunable Indolizine-Based Fluorophores and Fluorescent pH Sensor." Molecules 27, no. 1 (December 21, 2021): 12. http://dx.doi.org/10.3390/molecules27010012.

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A new fluorescent indolizine-based scaffold was developed using a straightforward synthetic scheme starting from a pyrrole ring. In this fluorescent system, an N,N-dimethylamino group in the aryl ring at the C-3 position of indolizine acted as an electron donor and played a crucial role in inducing a red shift in the emission wavelength based on the ICT process. Moreover, various electron-withdrawing groups, such as acetyl and aldehyde, were introduced at the C-7 position of indolizine, to tune and promote the red shift of the emission wavelength, resulting in a color range from blue to orange (462–580 nm). Furthermore, the ICT effect in indolizine fluorophores allowed the design and development of new fluorescent pH sensors of great potential in the field of fluorescence bioimaging and sensors.

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13

Zhang, Yi-Zhu, Feng-Tao Sheng, Zuoquan Zhu, Zhi-Ming Li, Shu Zhang, Wei Tan, and Feng Shi. "Organocatalytic C3-functionalization of indolizines: synthesis of biologically important indolizine derivatives." Organic & Biomolecular Chemistry 18, no. 29 (2020): 5688–96. http://dx.doi.org/10.1039/d0ob01230k.

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A Brønsted acid-catalyzed C3-alkylation of indolizines has been established with different electrophiles (E), which synthesized a series of C3-functionalized indolizines in overall good yields (up to 89%).

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14

Wang, Yefei, Zhen Yang, Fengtao Zhan, Zhifeng LYu, Chengyou Han, Xiaonuo Wang, Wuhua Chen, Mingchen Ding, Renzhuo Wang, and Yingnan Jiang. "Correction: Indolizine quaternary ammonium salt inhibitors part II: a reinvestigation of an old-fashioned strong acid corrosion inhibitor phenacyl quinolinium bromide and its indolizine derivative." New Journal of Chemistry 43, no. 43 (2019): 17123–24. http://dx.doi.org/10.1039/c9nj90149c.

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Correction for ‘Indolizine quaternary ammonium salt inhibitors part II: a reinvestigation of an old-fashioned strong acid corrosion inhibitor phenacyl quinolinium bromide and its indolizine derivative’ by Yefei Wang et al., New J. Chem., 2018, 42, 12977–12989.

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15

Tallarita, Roberto, Lukas Manuel Jacobsen, Benedict J. Elvers, Stefan Richter, Siva S. M. Bandaru, Jevy V. Correia, and Carola Schulzke. "Synthesis of Seven Indolizine-Derived Pentathiepines: Strong Electronic Structure Response to Nitro Substitution in Position C-9." Molecules 29, no. 1 (December 30, 2023): 216. http://dx.doi.org/10.3390/molecules29010216.

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Seven new 1,2,3,4,5-pentathiepino[6,7-a]indolizines were synthesized in which the pentathiepine moieties bear an indolizine backbone that is derivatized from C–H to F-, Cl-, Br-, I-, NO2-, and CH3-substitutions, respectively, in a meta position relative to the aza group on the pyridine moiety. Their preparation took place via two common steps: (i) a Sonogashira coupling between (4-substituted) 2-bromo- or 2-chloropyridines and propynyl 3,3-diethylacetal, and (ii) a ring closing reaction mediated by a molybdenum oxo-bistetrasulfido complex and elemental sulfur. The latter simultaneously facilitates the 1,2,3,4,5-pentathiepino chain/ring- and indolizine ring-formations. The fluoro derivative was addressed with 2-bromo-5-aminopyridine as the starting material via a Sandmeyer reaction. The iodo derivative was obtained from 5-bromo-2-alkynylpiridine using a metal-assisted variation of the Finkelstein reaction. The requirement to explore different reaction conditions and the varied respective yields of the final products are discussed. The influence of the distinct substitutions on the pyridine moieties, their electronic structures, and respective chemical properties was investigated through a set of spectroscopic/analytical characterizations. Intriguingly, in all cases, the nitro-substituted derivative exhibited a distinct behavior compared to the six other investigated derivatives, which was also addressed computationally. All seven new pentathiepines were crystallized, and their respective molecular structures were determined using single crystal X-ray diffraction. These structures are compared and discussed as are their respective packing patterns.

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16

Vrábel, Viktor, Július Sivý, Peter Šafář, and Jozef Kožíšek. "(11aS)-1,5,11,11a-Tetrahydro-1-benzothieno[3,2-f]indolizin-3(2H)-one." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (November 23, 2013): o1819—o1820. http://dx.doi.org/10.1107/s1600536813031693.

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The absolute configuration of the title compound, C14H13NOS, was assigned from the synthesis and confirmed by the structure determination. There are two independent molecules in the asymmetric unit. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviations from the mean planes being 0.569 (3) and 0.561 (3) Å for the indolizine bridgehead C atoms of the two molecules. The benzothieno ring attached to the indolizine ring system is planar to within 0.015 (3) Å in both molecules. In the crystal, weak C—H...O and C—H...π interactions lead to the formation of a three-dimensional framework structure.

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17

Romo, Pablo E., Jairo Quiroga, Justo Cobo, and Christopher Glidewell. "Synthesis and spectroscopic and structural characterization of spiro[indoline-3,3′-indolizine]s formed by 1,3-dipolar cycloadditions between isatins, pipecolic acid and an electron-deficient alkene." Acta Crystallographica Section C Structural Chemistry 77, no. 9 (August 6, 2021): 496–504. http://dx.doi.org/10.1107/s2053229621007142.

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Five new spiro[indoline-3,3′-indolizine]s have been synthesized with high regio- and stereospecificity in one-pot three-component reactions between a substituted indole-2,3-dione, (S)-pipecolic acid and trans-3-benzoylacrylic acid, and subsequently characterized using a combination of elemental analysis, IR and 1H and 13C NMR spectroscopy, mass spectrometry and crystal structure analysis. (1′SR,2′SR,3RS,8a′RS)-2′-Benzoyl-5-fluoro-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C23H21FN2O4, (I), and (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-5-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C24H24N2O4, (II), are isomorphous, as are (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-1-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C24H24N2O4, (III), and (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-5-chloro-1-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C24H23ClN2O4, (IV). Within each isomorphous pair, the spiro ring systems show some conformational differences. In each of (I) and (II), the molecules are linked into complex sheets by a combination of four types of hydrogen bond, and in each of (III) and (IV), a combination of O—H...O and C—H...π(arene) hydrogen bonds links the molecules to form a chain of centrosymmetric rings. In (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-1-hexyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C29H34N2O4, (V), a combination of five hydrogen bonds links the molecules into sheets of alternating R 2 2(16) and R 6 6(46) rings. A mechanism is proposed for the formation of compounds (I)–(V) and some comparisons with related structures are made.

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18

Saucier, Matthew A., Cameron Smith, Nicholas A. Kruse, Nathan I. Hammer, and Jared H. Delcamp. "Acid-Triggered Switchable Near-Infrared/Shortwave Infrared Absorption and Emission of Indolizine-BODIPY Dyes." Molecules 28, no. 3 (January 29, 2023): 1287. http://dx.doi.org/10.3390/molecules28031287.

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Fluorescent organic dyes that absorb and emit in the near-infrared (NIR, 700–1000 nm) and shortwave infrared (SWIR, 1000–1700 nm) regions have the potential to produce noninvasive high-contrast biological images and videos. BODIPY dyes are well known for their high quantum yields in the visible energy region. To tune these chromophores to the NIR region, fused nitrogen-based heterocyclic indolizine donors were added to a BODIPY scaffold. The indolizine BODIPY dyes were synthesized via microwave-assisted Knoevenagel condensation with indolizine aldehydes. The non-protonated dyes showed NIR absorption and emission at longer wavelengths than an aniline benchmark. Protonation of the dyes produced a dramatic 0.35 eV bathochromic shift (230 nm shift from 797 nm to 1027 nm) to give a SWIR absorption and emission (λmaxemis = 1061 nm). Deprotonation demonstrates that material emission is reversibly switchable between the NIR and SWIR.

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19

Bode, Moira L., and Perry T. Kaye. "Indolizine studies. Part 2. Synthesis and NMR spectroscopic analysis of 2-substituted indolizines." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (1993): 1809. http://dx.doi.org/10.1039/p19930001809.

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20

Cai, Qun, Yan-Ping Zhu, Yang Gao, Jing-Jing Sun, and An-Xin Wu. "A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives." Canadian Journal of Chemistry 91, no. 6 (June 2013): 414–19. http://dx.doi.org/10.1139/cjc-2012-0534.

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A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylide synthesis, and 1,3-dipolar cycloaddition. The protocols were found to be highly efficient in terms of high yields, operational simplicity, mild reaction conditions, and easy workup. This method has provided an important supplement for the synthesis of indolizine derivatives via a novel tandem synthesis.

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21

Chandrashekharappa, Sandeep, Katharigatta N. Venugopala, Christophe Tratrat, Fawzi M. Mahomoodally, Bandar E. Aldhubiab, Michelyne Haroun, Rashmi Venugopala, et al. "Efficient synthesis and characterization of novel indolizines: exploration of in vitro COX-2 inhibitory activity and molecular modelling studies." New Journal of Chemistry 42, no. 7 (2018): 4893–901. http://dx.doi.org/10.1039/c7nj05010k.

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22

Shen, Yong-Miao, Hoong-Kun Fun, and Jian-Hua Xu. "Dimethyl indolizine-1,6-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (August 25, 2006): o4080—o4081. http://dx.doi.org/10.1107/s1600536806033411.

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23

Gu, Wei-Jin, Jin Zhuang, Yu-Liang Jiang, and Bing-Xiang Wang. "Diethyl indolizine-1,3-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 67, no. 1 (December 15, 2010): o123. http://dx.doi.org/10.1107/s1600536810050919.

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24

Ji, Ruixue, Aikun Liu, Shili Shen, Xiaoqun Cao, Fei Li, and Yanqing Ge. "An indolizine–rhodamine based FRET fluorescence sensor for highly sensitive and selective detection of Hg2+ in living cells." RSC Advances 7, no. 65 (2017): 40829–33. http://dx.doi.org/10.1039/c7ra07938a.

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25

Naik, T. R. Ravikumar, G. Mahanthesha, and T. Suresh. "Synthesis and Biological Evaluation of (4-Fluorophenyl)(1-(5-phenyl-1,3,4-oxadiazol-2-yl)indolizin-3-yl)methanone Derivatives as Anti-cancer and Antimicrobial Agents." International Journal of Pharmaceutical Sciences and Drug Research 14, no. 01 (January 31, 2022): 8–18. http://dx.doi.org/10.25004/ijpsdr.2022.140102.

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A novel series of (4-Fluorophenyl (1-(5-phenyl-1,3,4-oxadiazol-2-yl)indolizin-3-yl)methanone derivatives 9(a-n) were synthesized by the coupling reaction of 3-(4-fluorobenzoyl)indolizine-1-carboxylic acid and substituted benzohydrazide followed by intramolecular cyclization. The structures of the compounds were characterized by 1 H NMR, 13C NMR, LCMS, FT-IR, and elemental analyses. The compounds 9(a-n) anti-cancer activity was evaluated against the MCF-7 cell line (HTB-22, Homo sapiens, Breast carcinoma). Compound 9j (IC50 = 21.57 µM), and 9n (IC50 = 8.52 µM) exhibited the most potent cytotoxicity activity compared with standard drug doxorubicin (IC50= 25.71). The antibacterial activity was evaluated against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 8739. The compounds ZOI=16mm) and 9i (ZOI=18 mm) exhibited moderate antibacterial activity compared with standard drug ciprofloxacin. The antifungal activity was evaluated against Candida albicans ATCC 10231. Most compounds exhibited moderate antifungal activity compared with the standard drug Itraconazole.

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26

Yang, Jie, Yifan Zhu, Anfernee Kai-Wing Tse, Xinghua Zhou, Yang Chen, Yu Chung Tse, Keith Man-Chung Wong, and Chun-Yu Ho. "Synthesis and study of Au(iii)–indolizine derivatives: turn-on luminescence by photo-induced controlled release." Chemical Communications 55, no. 31 (2019): 4471–74. http://dx.doi.org/10.1039/c8cc10177a.

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27

Bode, Moira L., Perry T. Kaye, and Rosemary George. "Indolizine studies. Part 3. Synthesis and dynamic NMR analysis of indolizine-2-carboxamides." Journal of the Chemical Society, Perkin Transactions 1, no. 20 (1994): 3023. http://dx.doi.org/10.1039/p19940003023.

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28

Kakehi, Akikazu, Suketaka Ito, Shin-ichi Matsumoto, and Yuichiro Morimoto. "Regiospecific Formations of Thieno[3,2-a]indolizine and Thieno[2,3-b]indolizine Derivatives." Chemistry Letters 16, no. 10 (October 5, 1987): 2043–46. http://dx.doi.org/10.1246/cl.1987.2043.

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29

Wang, Yefei, Zhen Yang, Fengtao Zhan, Zhifeng LYu, Chengyou Han, Xiaonuo Wang, Wuhua Chen, Mingchen Ding, Renzhuo Wang, and Yingnan Jiang. "Indolizine quaternary ammonium salt inhibitors part II: a reinvestigation of an old-fashioned strong acid corrosion inhibitor phenacyl quinolinium bromide and its indolizine derivative." New Journal of Chemistry 42, no. 15 (2018): 12977–89. http://dx.doi.org/10.1039/c8nj02505c.

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30

Foster, C., M. Ritchie, D. L. Selwood, and W. Snowden. "Synthesis and Anti-Herpes Activity of a Series of Indolizines." Antiviral Chemistry and Chemotherapy 6, no. 5 (October 1995): 289–97. http://dx.doi.org/10.1177/095632029500600502.

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A systematic screening study identified 2-phenyl-indolizine [1] as having significant human cytomegalovirus (HCMV) activity (IC50 = 7-19 μM). Preliminary mode of action studies on infected cells treated with [1] indicated supression of HCMV-related polypeptides with little effect on the host cells. A series of analogues were synthesized, some of which showed improved HCMV activity although with lower therapeutic indices than [1]. Several analogues demonstrated significant varicella zoster virus activity, with 2-(4-cyanophenyl)indolizine [5] having an IC50 of 5 μM and a therapeutic index of 20 over cell toxicity in the MRC 5 cell line.

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31

Sarkar, Rajib, Tandrima Chaudhuri, Animesh Karmakar, and Chhanda Mukhopadhyay. "Synthesis and photophysics of selective functionalized π-conjugated, blue light emitting, highly fluorescent C7-imidazo indolizine derivatives." Organic & Biomolecular Chemistry 13, no. 48 (2015): 11674–86. http://dx.doi.org/10.1039/c5ob01646k.

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32

Liu, Ren-Rong, Zheng-Yi Cai, Chuan-Jun Lu, Shi-Chun Ye, Bin Xiang, Jianrong Gao, and Yi-Xia Jia. "Indolizine synthesis via Cu-catalyzed cyclization of 2-(2-enynyl)pyridines with nucleophiles." Organic Chemistry Frontiers 2, no. 3 (2015): 226–30. http://dx.doi.org/10.1039/c4qo00336e.

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33

Huang, Cheng, Zhifei Zhao, Shiwu Li, Jixing Zhao, Leifang Wu, and Chengzhi Gu. "Catalytic asymmetric conjugate addition of indolizines to unsaturated ketones catalyzed by chiral-at-metal complexes." Organic Chemistry Frontiers 9, no. 7 (2022): 1932–36. http://dx.doi.org/10.1039/d1qo01657a.

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34

Huckaba, Aron J., Aswani Yella, Phillip Brogdon, J. Scott Murphy, Mohammad Khaja Nazeeruddin, Michael Grätzel, and Jared H. Delcamp. "A low recombination rate indolizine sensitizer for dye-sensitized solar cells." Chemical Communications 52, no. 54 (2016): 8424–27. http://dx.doi.org/10.1039/c6cc02247b.

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35

Chatterjee, Satadru, William E. Meador, Cameron Smith, Indika Chandrasiri, Mohammad Farid Zia, Jay Nguyen, Austin Dorris, et al. "SWIR emissive RosIndolizine dyes with nanoencapsulation in water soluble dendrimers." RSC Advances 11, no. 45 (2021): 27832–36. http://dx.doi.org/10.1039/d1ra05479a.

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36

AbdelSamad, Amr L., Mohammed T. El-Saadi, Ahmed M. Gouda, and Asmaa M. AboulMagd. "Pyrrolizine/indolizine-bearing (un)substituted isoindole moiety: design, synthesis, antiproliferative and MDR reversal activities, and in silico studies." RSC Advances 13, no. 44 (2023): 30753–70. http://dx.doi.org/10.1039/d3ra05310e.

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37

Au-Alvarez, O., V. A. Tafeenko, and L. A. Aslanov. "Structural study of indolizine derivatives." Acta Crystallographica Section A Foundations of Crystallography 52, a1 (August 8, 1996): C274. http://dx.doi.org/10.1107/s010876739608854x.

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38

Kaupp, Gerd, and Ernst Ringer. "The first photocycloadditions of indolizine." Tetrahedron Letters 28, no. 49 (January 1987): 6155–58. http://dx.doi.org/10.1016/s0040-4039(00)61834-8.

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39

Sharma, Vikas, and Vipin Kumar. "Indolizine: a biologically active moiety." Medicinal Chemistry Research 23, no. 8 (February 27, 2014): 3593–606. http://dx.doi.org/10.1007/s00044-014-0940-1.

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40

Birr, Emil-Joachim, and Werner Walther. "Zur Konstitution der Triaza-indolizine." Chemische Berichte 86, no. 11 (January 21, 2006): 1401–3. http://dx.doi.org/10.1002/cber.19530861104.

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41

Bonnaud, Bernard, Dennis Bigg, and Jean-François Patoiseau. "Synthesis of novel indolizine derivatives." Journal of Heterocyclic Chemistry 28, no. 8 (December 1991): 1927–32. http://dx.doi.org/10.1002/jhet.5570280820.

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42

Tukulula, Matshawandile, Rosalyn Klein, and Perry T. Kaye. "Indolizine Studies, Part 5: Indolizine-2-carboxamides as Potential HIV-1 Protease Inhibitors[1]." Synthetic Communications 40, no. 13 (June 16, 2010): 2018–28. http://dx.doi.org/10.1080/00397910903219450.

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43

Bloch, Witold M., Stephanie M. Derwent-Smith, Fatiah Issa, Jonathan C. Morris, Louis M. Rendina, and Christopher J. Sumby. "Fused pyrazino[2,3-b]indolizine and indolizino[2,3-b]quinoxaline derivatives; synthesis, structures, and properties." Tetrahedron 67, no. 48 (December 2011): 9368–75. http://dx.doi.org/10.1016/j.tet.2011.09.133.

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44

BODE, M. L., and P. T. KAYE. "ChemInform Abstract: Indolizine Studies. Part 2. Synthesis and NMR Spectroscopic Analysis of 2-Substituted Indolizines." ChemInform 24, no. 51 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199351191.

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45

Ceder, Olof, and Mohammed Rashid Sharif. "The reaction of indolizines with esters of orthoformic acid: synthesis of tris-indolizine molecular propellers." Chemische Berichte 120, no. 2 (February 1987): 239–42. http://dx.doi.org/10.1002/cber.19871200217.

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46

Chen, Hong-Ru, Zhen-Yu Hu, Hua-Li Qin, and Haolin Tang. "A novel three-component reaction for constructing indolizine-containing aliphatic sulfonyl fluorides." Organic Chemistry Frontiers 8, no. 6 (2021): 1185–89. http://dx.doi.org/10.1039/d0qo01430c.

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47

Li, Jinbiao, Shuaizhong Zhang, and Hongbin Zou. "One-pot chemoselective domino condensation to form a fused pyrrolo–pyrazino–indolizine framework: discovery of novel AIE molecules." Organic Chemistry Frontiers 7, no. 10 (2020): 1218–23. http://dx.doi.org/10.1039/d0qo00274g.

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48

López, Luis A., and Javier González. "Copper(i)-carbenes as key intermediates in the [3 + 2]-cyclization of pyridine derivatives with alkenyldiazoacetates: a computational study." Organic & Biomolecular Chemistry 17, no. 3 (2019): 646–54. http://dx.doi.org/10.1039/c8ob02676a.

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This work reports a computational study of the copper(i)-catalyzed regioselective synthesis of indolizine derivatives through the [3 + 2]-cyclization reaction of vinyldiazo acetates and pyridine derivatives.

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49

Dong, Shanliang, Jingjing Huang, Hongkai Sha, Lihua Qiu, Wenhao Hu, and Xinfang Xu. "Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazoacetates and pyridines: access to polycyclic indolizines." Organic & Biomolecular Chemistry 18, no. 10 (2020): 1926–32. http://dx.doi.org/10.1039/d0ob00222d.

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A copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazo compounds with pyridines, which affords polycyclic fused indolizine derivatives with broad substrate generality, has been reported.

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50

Su, Kexin, Xin Guo, Liangwei Zhu, Yafeng Liu, Yixuan Lu, and Baohua Chen. "Indolizine synthesis via radical cyclization and demethylation of sulfoxonium ylides and 2-(pyridin-2-yl)acetate derivatives." Organic Chemistry Frontiers 8, no. 15 (2021): 4177–82. http://dx.doi.org/10.1039/d1qo00550b.

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A novel radical cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and sulfoxonium ylides is developed, which provides a straightforward access to structurally diverse methylthio-substituted indolizine.

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