Potential inhibitors of L-asparagine biosynthesis. 5. Electrophilic amide analogs of (S)-2,3-diaminopropionic acid
- 1 May 1981
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 24 (5), 554-559
- https://doi.org/10.1021/jm00137a015
Abstract
Three electrophilic amide analogs of (S)-2,3-diaminopropionic acid (DAP) were prepared as potential inhibitors of L-asparagine synthetase (ASase, from [rat] Novikoff hepatoma, EC 6.3.5.4): (S)-2-amino-3-(2-bromoacetamido)propionic acid hydrobromide (7a), (S)-2-amino-3-(2,2-dichloroacetamido)propionic acid (7b) and ethyl N-[(S)-2-amino-2-carboxyethyl]fumarate (7c). The inhibition of ASase by 7a-c at 1 mM was 93, 19, and 37%, respectively. Compounds 7a-c failed to increase the life span of mice infected with B16 melanoma.This publication has 3 references indexed in Scilit:
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- ASPARAGINE BIOSYNTHESIS BY NOVIKOFF HEPATOMA - ISOLATION PURIFICATION PROPERTY AND MECHANISM STUDIES OF ENZYME SYSTEM1968
- The Isolation and Characterization of β-N-Oxalyl-L-α,β-Diaminopropionic Acid: A Neurotoxin from the Seeds of Lathyrus sativus*Biochemistry, 1964