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Synthesis and chemical reactivity of c‐5 substituted 6,7‐bis‐(hydroxymethyl)‐1 H ‐pyrrolizine biscarbamate tumor inhibitors
Author(s) -
Anderson Wayne K.,
Mach Robert H.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270440
Subject(s) - chemistry , reactivity (psychology) , hydroxymethyl , pyridine , nucleophile , alkylation , stereochemistry , chemical synthesis , in vitro , medicinal chemistry , organic chemistry , biochemistry , catalysis , medicine , alternative medicine , pathology
A series of C‐5 substituted pyrrolizine biscarbamate alkylating agents were synthesized and evaluated in an in vitro alkylation assay. Introduction of electron‐withdrawing substituents at the C‐5 position resulted in a dramatic decrease in chemical reactivity toward the model nucleophile 4‐(4‐nitrobenzyl)pyridine (NBP).