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Synthesis and Antimicrobial Activities of Some New Tetrahydro‐2 H ‐1,3,5‐thiadiazine‐2‐thione Derivatives of Cefadroxil
Author(s) -
Saraç Selma,
Ertan Mevlüt,
Balkan Ayla,
Yulug Nuran
Publication year - 1991
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.19913240709
Subject(s) - cefadroxil , antimicrobial , chemistry , microbiology and biotechnology , nuclear chemistry , organic chemistry , biology , biochemistry , cephalosporin , antibiotics
Abstract Eleven new 7‐[2‐(dihydro‐5‐substituted‐6‐thioxo‐2 H ‐1,3,5‐thiadiazine‐3(4 H )‐yl)‐2‐(4‐hydroxyphenyl)acetamido]‐3‐methyl‐3‐cephem‐4‐carboxylic acid derivatives were synthesized by the reaction of cefadroxil monohydrate, formaldehyde and substituted potassium dithiocarbamate. Their structures have been elucidated by spectral data and elementary analysis. The title compounds were tested for antimicrobial activity in vitro against gram‐positive bacteria ( Staphylococcus aureus, Streptococcus faecalis ), gram‐negative bacteria ( Escherichia coli, Pseudomonas aeruginosa ) and yeast‐like fungi ( Candida albicans, C. parapsilosis, C. stellatoidea, C. pseudotropicalis ) in comparison with cefadroxil monohydrate. The activity of compounds 1 and 10 against S. aureus (MBC: 37.5 μg/ml) and compound 1 against E. coli (MBC: 75 μg/ml) were found to be the same as cefadroxil monohydrate. Compounds 1 and 10 were more effective than cefadroxil monohydrate against S. faecalis with 25 and 37.5 μg/ml MBC values, respectively. None of the compounds and cefadroxil monohydrate proved to be effective against P. aeruginosa (MBC: > 100 μg/ml). While cefadroxil monohydrate had no activity against yeast‐like fungi, compounds 9 and 10 were significantly effective against yeast‐like fungi (MFC: 37.5 μg/ml).