A Convenient Procedure for the Synthesis of O⁶-Benzylguanine Derivatives by Phase Transfer Catalysis

Abstract

A convenient procedure by phase transfer catalysis has been developed for the synthesis of O⁶-BG (1) and its derivatives hydroxymethyl-BG (2a–c), halo-BG (3a–c, 4a–c, 5a–c, 6a–c), methoxy-BG (7), and methyl-BG (8). Compounds 2b, 2c, 4b, 4c, 5b, 5c, 6a, and 6c are new compounds.

Keywords:

• O⁶-Benzylguanine derivatives
• Synthesis
• Phase transfer catalysis
• O⁶-Alkylguanine-DNA alkyltransferase

Acknowledgments

This work is supported by the National Institutes of Health/National Cancer Institute grant P20CA86350 (to GDH), the Susan G. Komen Breast Cancer Foundation grant IMG 2000 837 (to QHZ), Indiana University American Cancer Society Institutional Grant Committee grant IRG-84-002-17 (to QHZ), and Indiana 21st Century Research & Technology Fund grant (to GDH).