Resveratrol, a naturally occurring stilbene in fruits and wines, possesses anticancer properties. Its ability to inhibit Human Cytochrome P450 (CYP450) provides a possible mechanism for preventing tumor formation. This has created an interest in synthesizing and testing substituted (E)-stilbenes on CYP450. The synthesis of substituted (E)-stilbenes involves a palladium(II) catalyzed Heck-type coupling that utilizes a diazonium ion generated in situ from a prepared liner triazene intermediate. These intermediates, their starting materials, morpholine and various substituted anilines, and their corresponding final (E)-stilbene products were screened for possible inhibition of CYP450 1A1 and 1B1. Overall, the intermediate triazenes inhibited the CYP450 enzymes more than the other types of compounds tested with 4-[(E)-2-(3,4,5-trimethoxyphenyl)diazenyl)]morpholine and 4-[(E)-2-(3,5-dimethoxyphenyl)diazenyl]morpholine having the greatest inhibition. The IC-50 for 4-[(E)-2-(3,4,5-trimethoxyphenyl)diazenyl)]morpholine was 10.31 �M and 17.80 �M with CYP4501A1 and CYP4501B1, respectively. The IC-50 for 4-[(E)-2-(3,5-dimethoxyphenyl)diazenyl]morpholine was 14.32 �M and 8.55 �M with CYP4501A1 and CYP4501B1, respectively.

Triazenes inhibit cytochrome P450 1A1 and 1B1 as a potential means to prevent cancer

245th National Meeting (2013)

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