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Molecules 2016, 21(2), 154;

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

Department of Chemistry, Section of Organic Chemistry and Biochemistry, University of Ioannina, 451 10 Ioannina, Greece
Academic Editor: Panayiotis A. Koutentis
Received: 17 September 2015 / Revised: 23 December 2015 / Accepted: 5 January 2016 / Published: 28 January 2016


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. View Full-Text
Keywords: small molecules; heterocycles; pyrrolobenzodiazepines; DNA-interactive agents; anticancer activity; anti-HIV activity small molecules; heterocycles; pyrrolobenzodiazepines; DNA-interactive agents; anticancer activity; anti-HIV activity

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Varvounis, G. An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines. Molecules 2016, 21, 154.

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