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Letteratura scientifica selezionata sul tema "Indoles"

Autore: Grafiati

Pubblicato: 4 giugno 2021

Ultima modifica: 7 settembre 2023

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Articoli di riviste sul tema "Indoles"

1

Sharma, Upendra, Inder Kumar e Rakesh Kumar. "Recent Advances in the Regioselective Synthesis of Indoles via C–H Activation/Functionalization". Synthesis 50, n. 14 (28 maggio 2018): 2655–77. http://dx.doi.org/10.1055/s-0037-1609733.

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Abstract (sommario):

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 e Cyrille Kouklovsky. "Dearomatization Reactions of Indoles to Access 3D Indoline Structures". Synlett 31, n. 18 (24 giugno 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, e 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, n. 18 (1 agosto 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, e Tõnis Kanger. "Enantioselective Catalytic Synthesis of N-alkylated Indoles". Symmetry 12, n. 7 (17 luglio 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 e Aijun Lin. "Pd(ii)-Catalyzed oxidative dearomatization of indoles: substrate-controlled synthesis of indolines and indolones". Organic Chemistry Frontiers 4, n. 2 (2017): 292–96. http://dx.doi.org/10.1039/c6qo00698a.

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6

Li, Jiao, e Chun-Lin Zhuang. "Natural Indole Alkaloids from Marine Fungi: Chemical Diversity and Biological Activities". Pharmaceutical Fronts 03, n. 04 (dicembre 2021): e139-e163. http://dx.doi.org/10.1055/s-0041-1740050.

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Abstract (sommario):

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 e 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, n. 5 (1 maggio 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 e Guisheng Zhang. "The dicarbonylation of indoles via Friedel–Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination". RSC Advances 6, n. 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, n. 24 (13 dicembre 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 e 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, n. 29 (2015): 22480–89. http://dx.doi.org/10.1039/c4ra16661b.

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Tesi sul tema "Indoles"

1

Scott, Karen Ann. "Synthetic studies related to the synthesis of vincristine". Thesis, University of Strathclyde, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.367067.

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2

Martin, Tracey. "Claisen rearragements in indoles". Thesis, Imperial College London, 1986. http://hdl.handle.net/10044/1/38097.

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3

Stempel, Erik [Verfasser]. "Construction of cyclohepta[b]indoles in the total synthesis of indole alkaloids / Erik Stempel". Hannover : Technische Informationsbibliothek (TIB), 2017. http://d-nb.info/1137165995/34.

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4

Keech, Peter George. "Electrochemical oxidation of simple indoles". Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp04/MQ61917.pdf.

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5

Mascal, Mark James. "Synthesis of 3,4-bridged indoles". Thesis, Imperial College London, 1989. http://hdl.handle.net/10044/1/47561.

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6

Jennings, Peter. "Photophysical study of electropolymerised indoles". Thesis, University of Edinburgh, 1999. http://hdl.handle.net/1842/12295.

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7

Harrison, Carrie-Ann. "Synthetic approaches to tremorgenic indoles". Thesis, Loughborough University, 1994. https://dspace.lboro.ac.uk/2134/32532.

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The literature on the synthesis of tremorgenic indoles is reviewed in Chapter 1. These compounds are of great importance to agriculture, especially in New Zealand and the United States of America, as they affect the central nervous system of livestock grazing infected pastures. The research centres on the synthesis of lolitrem B, a ten ring structure containing a central indole moiety. The central indole moiety is common for all of the tremorgenic indoles. To this end, studies on the preparation of a trans-fused hydrindane system and its incorporation into the central indole moiety are discussed in Chapter 2. Chapter 3 details investigations into the preparation of a pyrrole from a model used for the hydrindane system. Once obtained, the pyrrole is modified to give the pyranopyrrole, which, in turn, is reacted with dienophiles in Diels-Alder cycloadditions to give substituted indoles. Utilising the model for the hydrindane, studies on the Fischer indole reaction were undertaken to give substituted indoles. Modification of these led to the synthesis of the left-hand side of paspalitrem B. This work is discussed in Chapter 4. Preparation of the tetrahydrofuran portion of lolitrem B and incorporation onto the central indole moiety is detailed in Chapters 3 and 4.

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8

El, Marrouki Dalel. "Contribution à l’étude de la réactivité de quelques accepteurs de Michael cycliques et applications". Electronic Thesis or Diss., Université de Lorraine, 2020. http://www.theses.fr/2020LORR0197.

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Ce mémoire de thèse se concentre sur la synthèse d’hétérocycles azotés à partir d’une même famille de précurseurs : les 1,4-dicétones. Ces dernières ont été obtenues à travers deux voies de synthèse dont la première consiste en une réaction de Nef permettant la conversion des composés nitrés en cétones. La deuxième est une réaction de Wittig en utilisant divers ylures de Wittig et la cyclohexanedione. Ces intermédiaires réactionnels ont été utilisés par la suite pour la synthèse de dérivés indoliques via une réaction d’addition-1,2. Nous avons également pu orienter la sélectivité de la réaction vers la synthèse des indolones à partir d’une réaction d’addtion-1,4. En présence d’hydrazine monohydrate, les 1,4-dicétones ont aussi permis l’accès à des cinnolines avec d’excellents rendements
This thesis focuses on the synthesis of some nitrogenous heterocycles from the same family of precursors: 1,4-diketones. These 1,4-diketones have been obtained either by a Nef reaction through the conversion of nitro compounds into ketones or by a Wittig reaction using various Wittig ylides and cyclohexanedione. These reaction intermediates were subsequently used for the synthesis of indole derivatives via a 1,2-addition reaction. We were also able to turn the selectivity of the reaction towards the synthesis of indolones from a 1,4-addition reaction. With hydrazine monohydrate, 1,4-diketones have also provided access to cinnolines in excellent yields

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9

Hammoud, Sokaina. "Accès à de nouvelles structures tricycliques di-iodes à base indolique et isoindolique par iodocyclisation". Thesis, Tours, 2015. http://www.theses.fr/2015TOUR4034.

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Une nouvelle voie d’accès à des structures tri-cycliques originaux les « oxazino-indole di-iodés» a été mise au point à partir des acides 1H-indole-2-carboxyliques commerciaux ou des acides 1H-indole-2-carboxyliques fonctionnalisés obtenus par la réaction d’Hemetsberger-Knittel. La dernière étape de cette séquence est une réaction d’iodocyclisation qui s’est avérée totalement régio- et stéréosélective selon un processus de type 6-exo-dig. Cette méthodologie a ensuite été étendue en série isoindolique permettant un accès à des motifs « oxazino-isoindolique di-iodés » originaux. Afin d'étendre davantage cette méthodologie, de nouveaux « oxazepino-indole di-iodés » ont été préparés en utilisant la même approche synthétique à partir de l'acide 1H-indole-7-carboxylique. La réactivité des structures tri-cycliques di-iodés a été étudiée via des réactions de Cross-Coupling (Stille, Sonogashira, Suzuki) par l’utilisation de sels de palladium permettant une fonctionnalisation régiosélective de l’iode exocyclique
A new access pathway to the original tricyclic structures "di-iodinated oxazino-indole" was developed from the commercial 1H-indole-2-carboxylic acids or functionalized 1H-indole-2-carboxylic acid obtained by Hemetsberger-Knittel reaction. The last step in this sequence is an iodocyclisation reaction that is proved to be completely regio- and stereoselective via 6-exo-dig process. This methodology was then extended to isoindolic series allowing access to original "di-iodinated oxazino-isoindole" motifs. To further extend this methodology, new"di-iodinated oxazepino-indoles" were prepared using the same synthetic approach from the 1H-indole-7-carboxylic acid. The reactivity of the di-iodinated tri-cyclic structures has been studied via Cross-Coupling reactions (Stille, Sonogashira and Suzuki) by the use of palladium salts allowing a regioselective functionalization of the exocyclic iodine

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10

Westermaier, Martin. "Electrophilic Substitutions of Indoles and Pyrroles:". Diss., lmu, 2007. http://nbn-resolving.de/urn:nbn:de:bvb:19-77431.

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Libri sul tema "Indoles"

1

1927-, Saxton J. Edwin, a cura di. Indoles. Chichester: Wiley, 1994.

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2

service), SpringerLink (Online, a cura di. Heterocyclic Scaffolds II: Reactions and Applications of Indoles. Berlin, Heidelberg: Springer-Verlag Berlin Heidelberg, 2011.

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3

Voro, Tevita N. Synthesis of potentially biologically active indoles and pyrroles. Norwich: Universityof East Anglia, 1990.

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4

Murray, Paul Edward. [ Beta]-nucleophilic substitution in indoles: The synthesis of Chartellamide A. Manchester: University of Manchester, 1994.

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5

Benzies, David W. M. Some aspects of the synthesis and reactions of substituted indoles. Norwich: University of East Anglia, 1989.

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6

service), SpringerLink (Online, a cura di. Functional Phthalocyanine Molecular Materials. Berlin, Heidelberg: Springer-Verlag Berlin Heidelberg, 2010.

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7

1927-, Saxton J. Edwin, a cura di. Monoterpenoid indole alkaloids. Chichester [England]: Wiley, 1994.

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8

Gribble, Gordon W. Indole Ring Synthesis. Chichester, UK: John Wiley & Sons, Ltd, 2016. http://dx.doi.org/10.1002/9781118695692.

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9

Roffey, Maureen. Indoors. Martinez, CA: Discovery Books, 1989.

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10

Indoors. London: Collins Educational, 1992.

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Capitoli di libri sul tema "Indoles"

1

Brown, E. G. "Indoles". In Ring Nitrogen and Key Biomolecules, 192–207. Dordrecht: Springer Netherlands, 1998. http://dx.doi.org/10.1007/978-94-011-4906-8_9.

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2

Li, Jie Jack, e Minmin Yang. "Indoles". In Drug Discovery with Privileged Building Blocks, 143–51. Boca Raton: CRC Press, 2021. http://dx.doi.org/10.1201/9781003190806-17.

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3

Bronner, Sarah M., G. Yoon J. Im e Neil K. Garg. "Indoles and Indolizidines". In Heterocycles in Natural Product Synthesis, 221–65. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634880.ch7.

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4

Menendez-Pelaez, Armando, e Gerald R. Buzzell. "Harderian Gland Indoles". In Harderian Glands, 219–34. Berlin, Heidelberg: Springer Berlin Heidelberg, 1992. http://dx.doi.org/10.1007/978-3-642-76685-5_13.

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5

Joule, J. A., K. Mills e G. F. Smith. "Indoles: reactions and synthesis". In Heterocyclic Chemistry, 305–49. Boston, MA: Springer US, 1995. http://dx.doi.org/10.1007/978-1-4899-3222-8_17.

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6

Juwarker, Hemraj, Jae-min Suk e Kyu-Sung Jeong. "Indoles and Related Heterocycles". In Topics in Heterocyclic Chemistry, 177–204. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/7081_2010_31.

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7

Weedon, Alan. "The Photochemistry of Indoles". In Advances in Photochemistry, 229–77. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470133538.ch4.

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8

Muzalevskiy, Vasiliy M., Olga V. Serdyuk e Valentine G. Nenajdenko. "Chemistry of Fluorinated Indoles". In Fluorine in Heterocyclic Chemistry Volume 1, 117–56. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-04346-3_3.

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9

Sundberg, Richard J. "Electrophilic Substitution Reactions of Indoles". In Topics in Heterocyclic Chemistry, 47–115. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/7081_2010_52.

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Smith, Lowell R. "Alkyl, Alkenyl and Alkynyl Indoles". In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 65–126. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470186930.ch2.

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Atti di convegni sul tema "Indoles"

1

Wipf, Peter, e Filip Petronijevic. "New Approaches to Indoles and Indole Alkaloids". In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0388-1.

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2

Schauerte, Joseph A., e Ari Gafni. "Time Resolved Fluorescence Of Substituted Indoles". In OE/LASE '89, a cura di Robert R. Birge e Henry H. Mantsch. SPIE, 1989. http://dx.doi.org/10.1117/12.951649.

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3

Demchenko, Alexander P., Jacques Gallay e Michel Vincent. "Photophysics of indoles in polar environments". In Laser Applications in Life Sciences: 5th International Conference, a cura di Pavel A. Apanasevich, Nikolai I. Koroteev, Sergei G. Kruglik e Victor N. Zadkov. SPIE, 1995. http://dx.doi.org/10.1117/12.197412.

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4

Feu, Karla S., Anna M. Deobald, Arlene G. Corrêa e Marcio W. Paixão. "Tandem Organocatalytic Functionalization and Fisher Indole Synthesis: A Greener Approach for the Synthesis of Indoles". In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0342-1.

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5

Seijas, Julio, M. Vázquez-Tato, José Crecente-Campo, M. Gómez-Doval e Lorena Núñez-Álvarez. "Microwave assisted synthesis of indoles: Madelung's Reaction". In The 12th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2008. http://dx.doi.org/10.3390/ecsoc-12-01258.

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6

Ciprian-Ollivier, J., e M. G. Cetkovich-Bakmas. "METHYLATED INDOLES IN OBSESSIVE-COMPULSIVE AND PHOBIC DISORDERS". In IX World Congress of Psychiatry. WORLD SCIENTIFIC, 1994. http://dx.doi.org/10.1142/9789814440912_0009.

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7

Westbrook, John D., Ronald M. Levy e Karsten Krogh-Jespersen. "Simulation of photophysical processes of indoles in solution". In OE/LASE '92, a cura di Joseph R. Lakowicz. SPIE, 1992. http://dx.doi.org/10.1117/12.58196.

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8

Bagnoli, Luana, Katja Berettoni, Francesca Marini e Claudio Santi. "An efficient cascade reaction for the synthesis of oxazino[4,3-a]indoles and pyrano[3,4-b]indoles from vinyl selenones". In The 17th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2013. http://dx.doi.org/10.3390/ecsoc-17-a037.

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9

Muino, Pedro L., e Patrik R. Callis. "Simulations of solvent effects on fluorescence spectra and dynamics of indoles". In OE/LASE '94, a cura di Joseph R. Lakowicz. SPIE, 1994. http://dx.doi.org/10.1117/12.182745.

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10

Lapa, G., e O. Tolkachev. "A Novel Approach to the Synthesis of Substututed Indoles via Nitrilic Condensation." In The 3rd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1999. http://dx.doi.org/10.3390/ecsoc-3-01748.

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Rapporti di organizzazioni sul tema "Indoles"

1

Bjeldanes, Leonard. Control of Breast Tumor Cell Growth by Dietary Indoles. Fort Belvoir, VA: Defense Technical Information Center, settembre 1998. http://dx.doi.org/10.21236/adb240497.

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2

Chamovitz, A. Daniel, e Georg Jander. Genetic and biochemical analysis of glucosinolate breakdown: The effects of indole-3-carbinol on plant physiology and development. United States Department of Agriculture, gennaio 2012. http://dx.doi.org/10.32747/2012.7597917.bard.

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Abstract (sommario):

Genetic and biochemical analysis of glucosinolate breakdown: The effects of indole-3-carbinol on plant physiology and development Glucosinolates are a class of defense-related secondary metabolites found in all crucifers, including important oilseed and vegetable crops in the Brassica genus and the well-studied model plant Arabidopsis thaliana. Upon tissue damage, such as that provided by insect feeding, glucosinolates are subjected to catalysis and spontaneous degradation to form a variety of breakdown products. These breakdown products typically have a deterrent effect on generalist herbivores. Glucosinolate breakdown products also contribute to the anti-carcinogenic effects of eating cabbage, broccoli and related cruciferous vegetables. Indole-3-carbinol, a breakdown product of indol-3-ylmethylglucosinolate, forms conjugates with several other plant metabolites. Although some indole-3-carbinol conjugates have known functions in defense against herbivores and pathogens, most play as yet unidentified roles in plant metabolism, and possibly also plant development. At the outset, our proposal had three main hypotheses: (1) There is a specific detoxification pathway for indole-3-carbinol; (2) Metabolites derived from indole-3-carbinol are phloem-mobile and serve as signaling molecules; and (3) Indole-3-carbinol affects plant cell cycle and cell-differentiation pathways. The experiments were designed to enable us to elucidate how indole-3-carbinol and related metabolites affect plants and their interactions with herbivorous insects. We discovered that indole-3- carbinol rapidly and reversibly inhibits root elongation in a dose-dependent manner, and that this inhibition is accompanied by a loss of auxin activity in the root meristem. A direct interaction between indole-3-carbinol and the auxin perception machinery was suggested, as application of indole-3-carbinol rescued auxin-induced root phenotypes. In vitro and yeast-based protein interaction studies showed that indole-3-carbinol perturbs the auxin-dependent interaction of TIR1 with Aux/IAA proteins, supporting the notion that indole-3-carbinol acts as an auxin antagonist. Furthermore, transcript profiling experiments revealed the influence of indole-3-carbinol on auxin signaling in root tips, and indole-3-carbinol also affected auxin transporters. Brief treatment with indole-3-carbinol led to a reduction in the amount of PIN1 and to mislocalization of PIN2. The results indicate that chemicals induced by herbivory, such as indole-3-carbinol, function not only to repel herbivores, but also as signaling molecules that directly compete with auxin to fine tune plant growth and development, which implies transport of indole-3- carbinol that we are as yet unsuccessful in detecting. Our results indicate that plant defensive metabolites also have secondary functions in regulating aspects of plant metabolism, thereby providing diversity in defense-related plant signaling pathways. Such diversity of of signaling by defensive metabolites would be beneficial for the plant, as herbivores and pathogens would be less likely to mount effective countermeasures. We propose that growth arrest can be mediated directly by the herbivory-induced chemicals, in our case, indole-3-carbinol. Thus, glucosinolate breakdown to I3C following herbivory would have two outcomes: (1) Indole-3-carbinaol would inhibit the herbivore, while (2) at the same time inducing growth arrest within the plant. Thus, our results indicate that I3C is a defensive phytohormone that modulates auxin signaling, leading to growth arrest.

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3

Luo, Jun. Molecular Characterization of Indolent Prostate Cancer. Fort Belvoir, VA: Defense Technical Information Center, ottobre 2014. http://dx.doi.org/10.21236/ada613287.

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4

Luo, Jun. Molecular Characterization of Indolent Prostate Cancer. Fort Belvoir, VA: Defense Technical Information Center, ottobre 2013. http://dx.doi.org/10.21236/ada590674.

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5

Jerry D. Cohen. Metabolic regulation of the plant hormone indole-3-acetic acid. Office of Scientific and Technical Information (OSTI), novembre 2009. http://dx.doi.org/10.2172/966706.

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6

Cohen, Jerry D., Ephraim Epstein, Mark Roh e Joseph Riov. Indole-3-Acetic Acid Metabolism in Relation to Root Initiation. United States Department of Agriculture, ottobre 1985. http://dx.doi.org/10.32747/1985.7566592.bard.

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7

Fricker, Jon, Menna Noureldin, Timothy Stroshine e Wayne Richardson. Cost‐Effective Data Collection to Support INDOT’s Mission. Purdue University, dicembre 2012. http://dx.doi.org/10.5703/1288284315040.

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8

Ke, Yue, Lisa Lorena Losada-Rojas, Davis Chacon-Hurtado, Konstantina Gkritza e Jon D. Fricker. Incorporating Economic Resilience Metrics into INDOT’s Transportation Decision-Making. Purdue University, 2020. http://dx.doi.org/10.5703/1288284317115.

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9

Arboleda, Carlos, Hyung Jeong e Dulcy Abraham. Evaluation, Analysis, and Enhancement of INDOT's Utility Accommodation Policy. West Lafayette, IN: Purdue University, 2004. http://dx.doi.org/10.5703/1288284313220.

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Adsit, Sarah E., Theodora Konstantinou, Konstantina Gkritza e Jon D. Fricker. Public Acceptance of INDOT’s Traffic Engineering Treatments and Services. Purdue University, 2021. http://dx.doi.org/10.5703/1288284317280.

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Abstract (sommario):

As a public agency, interacting with and understanding the public’s perspective regarding agency activities is an important endeavor for the Indiana Department of Transportation (INDOT). Although INDOT conducts a biennial customer satisfaction survey, it is occasionally necessary to capture public perception regarding more specific aspects of INDOT’s activities. In particular, INDOT needs an effective way to measure and track public opinions and awareness or understanding of a select set of its traffic engineering practices. To evaluate public acceptance of specific INDOT traffic engineering activities, a survey consisting of 1.000 adults residing within the State of Indiana was conducted. The survey population was representative in terms of age and gender of the state as of the 2010 U.S. Census. The survey was administered during the months of July and August 2020. Public awareness regarding emerging treatments not currently implemented in Indiana is low and opposition to the same new technologies is prominent. Older or female drivers are less likely to be aware of emerging treatments, and older drivers are more likely to oppose potential implementation of these treatments. Although roundabouts are commonplace in Indiana, multi-lane roundabouts remain controversial among the public. Regarding maintenance and protection of traffic during work zones and considering full or partial roadway closure, public preference is for partial closure; this preference is stronger in rural areas. The public equally agrees and disagrees that INDOT minimizes construction related traffic delays. Approximately 76% of Indiana drivers believe themselves to above average drivers, while an additional 23% believe themselves to be average. Driver perceptions of average highway speeds speed are not aligned with posted speed limit as the perceived average speed on Indiana’s urban freeways and rural and urban state highways is considerably higher than the actual speed limit.

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