Premium
Contributions to the synthesis of some ferrocene‐containing antibiotics
Author(s) -
Scutaru D,
Tataru Lucia,
Mazilu I,
Vata M,
Lixandru Tatiana,
Simionescu Cr
Publication year - 1993
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590070402
Subject(s) - chemistry , thioglycolic acid , ferrocene , antibacterial activity , organic chemistry , bacteria , combinatorial chemistry , stereochemistry , electrode , biology , electrochemistry , genetics
This Review discusses the synthesis and characterization by our Group of new antibiotics belonging to the class of penicillins, cephalosporins and rifamycins with ferrocenyl and 1, 1′‐ferrocenilene residues in the molecule. As reactants for 6‐aminopenicillanic acid (6‐APA) and 7‐aminocephalosporanic acid (7‐ACA) the following were used: 1, 1‐bis(chlorocarbonyl)ferrocene, ferrocenyl sulfochloride, 1, 1′‐ferrocenylenedisulfochloride and thioglycolic acids S ‐modified with ferrocene. In the synthesis of rifamycins, the hydrazides of the thioglycolic acids, S ‐modified with ferrocene, were employed as nucleophilic agents. The synthesized intermediates were characterized by elemental analysis, TLC, IR, UV and 1 H NMR spectra. The characterization of new antibiotics was made by TLC, IR and UV spectral analysis. Biological activity was tested on Gram‐negative and Gram‐positive bacteria. Good activity is reported towards Gram‐positive bacteria in the case of derivatives containing residues of thioglycolic acid S ‐modified with ferrocene, the antibacterial activity being similar to that of amoxicillin, carbenicillin and cephalothin. All compounds are inactive towards Gram‐negative bacteria.