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An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines

Pyrrolo[1,4]benzodiazepines are tricyclic compounds that are considered “privileged structures” since they possess a wide range of biological activities. The first encounter with these molecules was the isolation of anthramycin from cultures of Streptomyces, followed by determination of the X-ray cr...

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Autor principal: Varvounis, George
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273195/
https://www.ncbi.nlm.nih.gov/pubmed/26828475
http://dx.doi.org/10.3390/molecules21020154
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author Varvounis, George
author_facet Varvounis, George
author_sort Varvounis, George
collection PubMed
description Pyrrolo[1,4]benzodiazepines are tricyclic compounds that are considered “privileged structures” since they possess a wide range of biological activities. The first encounter with these molecules was the isolation of anthramycin from cultures of Streptomyces, followed by determination of the X-ray crystal structure of the molecule and a study of its interaction with DNA. This opened up an intensive synthetic and biological study of the pyrrolo[2,1-c][1,4]benzodiazepines that has culminated in the development of the dimer SJG-136, at present in Phase II clinical trials. The synthetic efforts have brought to light some new synthetic methodology, while the contemporary work is focused on building trimeric pyrrolo[2,1-c][1,4]benzodiazepines linked together by various heterocyclic and aliphatic chains. It is the broad spectrum of biological activities of pyrrolo[1,2-a][1,4]benzodiazepines that has maintained the interest of researchers to date whereas several derivatives of the even less studied pyrrolo[1,2-d][1,4]benzodiazepines were found to be potent non-nucleoside HIV-1 reverse transcriptase inhibitors. The present review is an update on the synthesis of pyrrolo[2,1-c][1,4]benzodiazepines since the last major review of 2011, while the overview of the synthesis of the other two tricyclic isomers is comprehensive.
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spelling pubmed-62731952018-12-28 An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines Varvounis, George Molecules Review Pyrrolo[1,4]benzodiazepines are tricyclic compounds that are considered “privileged structures” since they possess a wide range of biological activities. The first encounter with these molecules was the isolation of anthramycin from cultures of Streptomyces, followed by determination of the X-ray crystal structure of the molecule and a study of its interaction with DNA. This opened up an intensive synthetic and biological study of the pyrrolo[2,1-c][1,4]benzodiazepines that has culminated in the development of the dimer SJG-136, at present in Phase II clinical trials. The synthetic efforts have brought to light some new synthetic methodology, while the contemporary work is focused on building trimeric pyrrolo[2,1-c][1,4]benzodiazepines linked together by various heterocyclic and aliphatic chains. It is the broad spectrum of biological activities of pyrrolo[1,2-a][1,4]benzodiazepines that has maintained the interest of researchers to date whereas several derivatives of the even less studied pyrrolo[1,2-d][1,4]benzodiazepines were found to be potent non-nucleoside HIV-1 reverse transcriptase inhibitors. The present review is an update on the synthesis of pyrrolo[2,1-c][1,4]benzodiazepines since the last major review of 2011, while the overview of the synthesis of the other two tricyclic isomers is comprehensive. MDPI 2016-01-28 /pmc/articles/PMC6273195/ /pubmed/26828475 http://dx.doi.org/10.3390/molecules21020154 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Varvounis, George
An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines
title An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines
title_full An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines
title_fullStr An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines
title_full_unstemmed An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines
title_short An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines
title_sort update on the synthesis of pyrrolo[1,4]benzodiazepines
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273195/
https://www.ncbi.nlm.nih.gov/pubmed/26828475
http://dx.doi.org/10.3390/molecules21020154
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