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Stereospecific synthesis and antibiotic activity of some cephalosporin analogs
Author(s) -
Bose Ajay K.,
Ram Bhagat,
Hoffman W. A.,
Hutchison A. J.,
Manhas M. S.
Publication year - 1979
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.5570160704
Subject(s) - chemistry , hydrogenolysis , stereospecificity , cephalosporin , lactam , raney nickel , antibacterial activity , cephalosporin antibiotic , stereochemistry , antibiotics , side chain , gram , combinatorial chemistry , organic chemistry , catalysis , bacteria , biochemistry , biology , genetics , polymer
The strategy used for the stereospecific synthesis of benzofused octams as cepham analogs was the conversion of a 3,4‐dihydrothioisocarbostyril to a thioimidate, cycloaddition reaction to form a fused β‐lactam and subsequent removal of the alkylthio group by Raney nickel hydrogenolysis. Using azidoacetyl chloride for forming the β‐lactam and following known procedures, an amido side chain was generated. Two of the carba analogs of cephalosporin so produced showed low levels of antibacterial activity against a number of gram positive and gram negative organisms.