"Synthesis of an aminopropyl analog of the experimental anticancer drug" by Moses Lee, Jacob E. Simpson et al.
 

Synthesis of an aminopropyl analog of the experimental anticancer drug tallimustine, and activation of its 4-nitrobenzylcarbamoyl prodrug by nitroreductase and NADH

ACS Citation

Lee, M.; Simpson, J. E.; Woo, S.; Kaenzig, C.; Anlezark, G. M.; Eno-Amooquaye, E.; Burke, P. J. Synthesis of an aminopropyl analog of the experimental anticancer drug tallimustine, and activation of its 4-nitrobenzylcarbamoyl prodrug by nitroreductase and NADH. Bioorg. Med. Chem. Lett. 1997, 7, 1065-1070.

Abstract

Compound 1, an analog of tallimustine that contains an aminopropyl group at the C-terminus, and its 4-nitrobenzylcarbamoyl prodrug 2 have been prepared. Analog 1 binds preferentially to the minor groove of poly(dA-dT) over poly(dG-dC), and is cytotoxic against the growth of LS1747 and SW1116 human colon cancer cells, with IC50 values of 0.02 μM and 10.0 μM, respectively. The prodrug 2 is significantly less cytotoxic (2.3 and 22.9 μM, respectively) than the parent drug 1. However, in the presence of nitroreductase and NADH prodrug 2 is as active as compound 1.

Source Name

Bioorganic & Medicinal Chemistry Letters

Publication Date

1-1-1997

Volume

7

Issue

8

Page(s)

1287-1291

Document Type

Citation

Citation Type

Article

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