Journal of Medicinal Chemistry

Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis [[[(alkylamino) carbonyl] oxy] methyl]-substituted 3-pyrrolines as prodrugs of …

WK Anderson, AS Milowsky

Index: Anderson, Wayne K.; Milowsky, Arnold S. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2241 - 2249

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Abstract

A series of bis [(carbamoyloxy) methyl] pyrrolines 2-4 were synthesized from either the appropriate a-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1, 3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were comparad to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl- ...