Journal of Medicinal Chemistry p. 1625 - 1631 (1994)
Update date:2022-08-05
Topics:
Boruah, Romesh
Skibo, Edward B.
The cytotoxicity and physical properties of the pyrrolo<1,2-a>benzimidazole (PBI) and pyrrolo<1,2-a>indole (PI) aziridinyl quinones were compared in order to assess the influence of the benzimidazole ring on antitumor activity and DNA reductive alkylation.Our studies show that the PI system possesses none of the cytotoxicity of the PBI systems.Unlike the PBIs, the PI system does not reductively alkylate DNA.Apparently, the benzimidazole ring favors reductive alkylation due to its electron deficient character compared to indole.In addition, the benzimidazole ringmay provide the hydrogen bonding interactions required for the interaction with DNA.Our findings resulted in the elucidation of a PBI pharmacophore.Inspection of the literature revealed another drug sharing the PBI pharmacophore, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione (EO9), which remarkably has cytotoxic properties similar to those of the PBIs.
View MoreYantai Jiacheng Chemical Technology Co., Ltd.
Contact:535-6303697,18663837927
Address:70# Qunying Road, Fushan District,Yantai, China
Zhuhai Rundu Pharmaceutical co.,Ltd
Contact:+86-756-7630755
Address:No.6,North Airport Road,Sanzao Town,Jinwan District
Chengdu D-Innovation Pharmaceutical Co., Ltd
Contact:86-28-85105536
Address:1001, B6, No.88 Keyuan South Road, Chengdu Hi-Tech Zone
Contact:027-87677569
Address:Room 2203, yujingmingmen Buidling One, xiongchu Road, wuhan city, hubei province, China
Contact:+86-577-65618087-605
Address:Room 402, Unit 4 Xinhu Bldg. Waitan Ruian City, Zhejiang China.
Doi:10.1007/BF00811678
(1994)Doi:10.1039/dt9960002309
(1996)Doi:10.1021/ja00089a006
(1994)Doi:10.1016/j.tetasy.2013.12.003
(2014)Doi:10.1021/jm00037a015
(1994)Doi:10.1002/ejoc.202100868
(2021)