Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles

Novel continuous-flow cascade reactions are developed for producing 1,4-diaryl-disubstituted dipolar γ-carbolines 2 that contain a carboxylate group and their two pentacyclic precursors 6, 7 from hemiindigos 1. The nucleophilic and pro-electrophilic chemistry described is new to the hemiindigos 1, a...

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Autores principales: Velezheva, V. S., Babii, O. L., Khodak, A. A., Alekseeva, E. A., Nelyubina, Yu V., Godovikov, I. A., Peregudov, A. S., Majorov, K. B., Nikonenko, B. V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9076487/
https://www.ncbi.nlm.nih.gov/pubmed/35541627
http://dx.doi.org/10.1039/c9ra07807j
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author Velezheva, V. S.
Babii, O. L.
Khodak, A. A.
Alekseeva, E. A.
Nelyubina, Yu V.
Godovikov, I. A.
Peregudov, A. S.
Majorov, K. B.
Nikonenko, B. V.
author_facet Velezheva, V. S.
Babii, O. L.
Khodak, A. A.
Alekseeva, E. A.
Nelyubina, Yu V.
Godovikov, I. A.
Peregudov, A. S.
Majorov, K. B.
Nikonenko, B. V.
author_sort Velezheva, V. S.
collection PubMed
description Novel continuous-flow cascade reactions are developed for producing 1,4-diaryl-disubstituted dipolar γ-carbolines 2 that contain a carboxylate group and their two pentacyclic precursors 6, 7 from hemiindigos 1. The nucleophilic and pro-electrophilic chemistry described is new to the hemiindigos 1, and it led to the discovery of antimycobacterial scaffold characteristic of rimino-type pentacycles 6, 7 and potent drug clofazimine. The new scaffold like clofazimine appears to be useful in developing lead agents active against drug-resistant/dormant TB.
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spelling pubmed-90764872022-05-09 Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles Velezheva, V. S. Babii, O. L. Khodak, A. A. Alekseeva, E. A. Nelyubina, Yu V. Godovikov, I. A. Peregudov, A. S. Majorov, K. B. Nikonenko, B. V. RSC Adv Chemistry Novel continuous-flow cascade reactions are developed for producing 1,4-diaryl-disubstituted dipolar γ-carbolines 2 that contain a carboxylate group and their two pentacyclic precursors 6, 7 from hemiindigos 1. The nucleophilic and pro-electrophilic chemistry described is new to the hemiindigos 1, and it led to the discovery of antimycobacterial scaffold characteristic of rimino-type pentacycles 6, 7 and potent drug clofazimine. The new scaffold like clofazimine appears to be useful in developing lead agents active against drug-resistant/dormant TB. The Royal Society of Chemistry 2019-12-13 /pmc/articles/PMC9076487/ /pubmed/35541627 http://dx.doi.org/10.1039/c9ra07807j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Velezheva, V. S.
Babii, O. L.
Khodak, A. A.
Alekseeva, E. A.
Nelyubina, Yu V.
Godovikov, I. A.
Peregudov, A. S.
Majorov, K. B.
Nikonenko, B. V.
Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
title Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
title_full Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
title_fullStr Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
title_full_unstemmed Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
title_short Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
title_sort novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9076487/
https://www.ncbi.nlm.nih.gov/pubmed/35541627
http://dx.doi.org/10.1039/c9ra07807j
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