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Synthesis of Antitumor Carbazole‐Amonafide Structural Hybrids
Author(s) -
Rozovsky Alex,
Regozin Elena,
OronHerman Mor,
Albeck Am,
Gellerman Gary
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403549
Subject(s) - chemistry , carbazole , nitrene , reagent , azide , yield (engineering) , combinatorial chemistry , stereochemistry , organic chemistry , materials science , metallurgy , catalysis
A facile synthesis of new antitumor [4,5‐ bc ]carbazole‐amonafide 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 IC 50 values.