Synthesis of 1-Indolyl-3,5,8-Substituted γ-Carbolines: One Pot Metal-Solvent Free Protocol and Biological Evaluation

Premansh Dudhe; Mena Asha Krishnan; Kratika Yadav; Diptendu Roy; Krishnan Venkatasubbaiah; Biswarup Pathak; Venkatesh Chelvam

doi:10.3762/bxiv.2020.131.v1

Synthesis of 1-Indolyl-3,5,8-Substituted γ-Carbolines: One Pot Metal-Solvent Free Protocol and Biological Evaluation

Premansh Dudhe ,
Mena Asha Krishnan ,
Kratika Yadav ,
Diptendu Roy ,
Krishnan Venkatasubbaiah ,
Biswarup Pathak and
Venkatesh Chelvam

Submitting author affiliation:

Indian Institute of Technology Indore, Indore, India

Beilstein Arch. 2020, 2020131. https://doi.org/10.3762/bxiv.2020.131.v1

Published 19 Nov 2020

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

1,5-Disubstituted indole-2-carboxaldehyde derivatives (1a–h) and glycine alkyl esters (2a–c) are shown to undergo a novel cascade imination-heterocylisation in the presence of organic base DIPEA to provide 1-indolyl 3,5,8-substituted g-carbolines (3aa–ea) in good yields. The g-carbolines are fluorescent and exhibit anticancer activities against cervical, lung, breast, skin and kidney cancers.

Keywords: γ-Carboline; cascade reaction; cytotoxicity; cell uptake; density functional theory; fluorescence.

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Dudhe, P.; Krishnan, M. A.; Yadav, K.; Roy, D.; Venkatasubbaiah, K.; Pathak, B.; Chelvam, V. Beilstein Arch. 2020, 2020131. doi:10.3762/bxiv.2020.131.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)