Synthesis of antitumor carbazole-amonafide structural hybrids

Alex Rozovsky; Elena Regozin; Mor Oron-Herman; Amnon Albeck; Gary Gellerman

doi:10.1002/ejoc.201403549

Synthesis of antitumor carbazole-amonafide structural hybrids

Alex Rozovsky
, Elena Regozin
, Mor Oron-Herman
, Amnon Albeck
, Gary Gellerman

Bar-Ilan University, Ariel University

Research output: Contribution to journal › Article › peer-review

Abstract

A facile synthesis of new antitumor [4,5-bc]carbazoleamonafide derivatives is described. These compounds represent a new class of structural hybrids that contain the medicinally important carbazole and amonafide cores. The synthesis involves a Suzuki-Miyaura coupling of bromoamonafide with arylboronic acid reagents followed by the introduction of an azide group and subsequent regiospecific thermal nitrene insertion to yield carbazole-amonafide hybrids in good yields. Preliminary antiproliferative assays against cancer and benign cell lines identified compounds with selective antitumor activity that exhibited submicromolar IC₅₀ values.

Original language	English
Pages (from-to)	1811-1818
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	8
DOIs	https://doi.org/10.1002/ejoc.201403549
State	Published - 1 Mar 2015

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Antitumor agents
Cross-coupling
DNA
Drug design
Medicinal chemistry
Nitrogen heterocycles

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201403549

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title = "Synthesis of antitumor carbazole-amonafide structural hybrids",

abstract = "A facile synthesis of new antitumor [4,5-bc]carbazoleamonafide derivatives is described. These compounds represent a new class of structural hybrids that contain the medicinally important carbazole and amonafide cores. The synthesis involves a Suzuki-Miyaura coupling of bromoamonafide with arylboronic acid reagents followed by the introduction of an azide group and subsequent regiospecific thermal nitrene insertion to yield carbazole-amonafide hybrids in good yields. Preliminary antiproliferative assays against cancer and benign cell lines identified compounds with selective antitumor activity that exhibited submicromolar IC50 values.",

keywords = "Antitumor agents, Cross-coupling, DNA, Drug design, Medicinal chemistry, Nitrogen heterocycles",

author = "Alex Rozovsky and Elena Regozin and Mor Oron-Herman and Amnon Albeck and Gary Gellerman",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2015",

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doi = "10.1002/ejoc.201403549",

language = "English",

volume = "2015",

pages = "1811--1818",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Synthesis of antitumor carbazole-amonafide structural hybrids

AU - Rozovsky, Alex

AU - Regozin, Elena

AU - Oron-Herman, Mor

AU - Albeck, Amnon

AU - Gellerman, Gary

PY - 2015/3/1

Y1 - 2015/3/1

N2 - A facile synthesis of new antitumor [4,5-bc]carbazoleamonafide derivatives is described. These compounds represent a new class of structural hybrids that contain the medicinally important carbazole and amonafide cores. The synthesis involves a Suzuki-Miyaura coupling of bromoamonafide with arylboronic acid reagents followed by the introduction of an azide group and subsequent regiospecific thermal nitrene insertion to yield carbazole-amonafide hybrids in good yields. Preliminary antiproliferative assays against cancer and benign cell lines identified compounds with selective antitumor activity that exhibited submicromolar IC50 values.

AB - A facile synthesis of new antitumor [4,5-bc]carbazoleamonafide derivatives is described. These compounds represent a new class of structural hybrids that contain the medicinally important carbazole and amonafide cores. The synthesis involves a Suzuki-Miyaura coupling of bromoamonafide with arylboronic acid reagents followed by the introduction of an azide group and subsequent regiospecific thermal nitrene insertion to yield carbazole-amonafide hybrids in good yields. Preliminary antiproliferative assays against cancer and benign cell lines identified compounds with selective antitumor activity that exhibited submicromolar IC50 values.

KW - Antitumor agents

KW - Cross-coupling

KW - DNA

KW - Drug design

KW - Medicinal chemistry

KW - Nitrogen heterocycles

UR - https://www.scopus.com/pages/publications/84929318955

U2 - 10.1002/ejoc.201403549

DO - 10.1002/ejoc.201403549

M3 - Article

SN - 1434-193X

VL - 2015

SP - 1811

EP - 1818

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 8

ER -

Synthesis of antitumor carbazole-amonafide structural hybrids

Abstract

UN SDGs

Keywords

ASJC Scopus subject areas

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