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Synthesis and Antibacterial Activity of 7β‐[3‐(Un)substituted‐2‐aminopropionamido]‐3‐vinylcephalosporins and Related Compounds
Author(s) -
Nestorova Boyka,
Pajpanova Tamara,
Simova Svetlana,
Tabakova Svoboda,
Golovinsky Evgeny,
Haimova Marietta
Publication year - 1995
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19953280615
Subject(s) - dipeptide , chemistry , acylation , stereochemistry , enantiomer , side chain , reagent , antibacterial activity , amino acid , biological activity , in vitro , organic chemistry , bacteria , biochemistry , catalysis , biology , polymer , genetics
A series of new 7β‐[3‐(un)substituted‐alanyl]‐3‐vinylcephalosporins and some related compounds, 4a – 1 is described. They incorporate residues of proteinogenic L ‐α‐aminocarboxylic acids, their antimetabolites and enantiomers as well as a dipeptide in the 7β‐acylamido side chain. The acylation of diphenyl‐methyl 7‐amino‐3‐vinyl‐3‐cephem‐4‐carboxylate ( 2 : R 2 = DPM) with various protected α‐aminocarboxylic acids 1a – k and the dipeptide 1l is carried out using TBTU as coupling reagent. The compounds, except 4f , are active in vitro against S. aureus and S. lutea , but only 4a, 4k , and 4l inhibit some of the Gram‐negative strains.