A vinylogous cephalosporine bearing a dihydroxythiophene moiety as a potential catechol surrogate has been synthesised (I-e-beta). Even if the anti staphylococcus spectrum displayed by this compound is of interest, its activity against Pseudomonas species, expected for such a structure, remains disappointing.
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http://dx.doi.org/10.1016/s0960-894x(99)00697-6 | DOI Listing |
Eur J Med Chem
September 2009
Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasnagar, Mangalore, Karnataka 575025, India.
A series of new 3,4-dipropyloxy-N(2),N(5)-bis(substituted)thiophene-2,5-dicarbohydrazides (4-30) were synthesized from ethyl thiodiglycolate and diethyloxalate through multistep reactions. Following Dieckmann-Komppa reaction, the required precursor 3,4-dihydroxythiophene-2,5-diester (1) was prepared. This was derivatized with propyl bromide and further converted to corresponding hydrazide (3), which was finally transformed to targeted hydrazones (4-30) by conventional methods.
View Article and Find Full Text PDFOrg Biomol Chem
March 2003
School of Chemistry, Queen's University of Belfast, Belfast, UK BT9 5AG.
Toluene dioxygenase (TDO)-catalysed sulfoxidation, using Pseudomonas putida UV4, was observed for the thiophene substrates 1A-1N. The unstable thiophene oxide metabolites, 6A-6G, 6K-6N, spontaneously dimerised yielding the corresponding racemic disulfoxide cycloadducts 7A-7G, 7K-7N. Dimeric or crossed [4 + 2] cycloaddition products, derived from the thiophene oxide intermediates 6A and 6D or 6B and 6D, were found when mixtures of thiophene substrates 1A and 1D or 1B and 1D were biotransformed.
View Article and Find Full Text PDFBioorg Med Chem Lett
February 2000
Medicinal Chemistry Department, Hoechst Marion Roussel, Romainville, France.
A vinylogous cephalosporine bearing a dihydroxythiophene moiety as a potential catechol surrogate has been synthesised (I-e-beta). Even if the anti staphylococcus spectrum displayed by this compound is of interest, its activity against Pseudomonas species, expected for such a structure, remains disappointing.
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