ISSN:
1434-193X
Keywords:
Antibiotics
;
Thiangazoles
;
Polythiazolines
;
Oxazoles
;
Structure-activity relationships
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The partial synthesis of 54 derivatives of thiangazole A (1a), a new polythiazoline antibiotic from Polyangium spec. (myxobacteria), is described. Derivatives with chemical modification of the carboxamide group in the oxazole region were prepared either by N-alkylation to amides 5-14 or by methanolysis to ester 15, and its transformation products 16, 19, 20. Oxidation of the C-5 methyl group of 1a with molecular oxygen led to the hydroxymethyl derivative 21, and two by-products lacking the C-5 methyl group (22), or the entire oxazole ring (23). Key intermediate for analogues with modifications in the styryl region is the aldehyde 27, obtained by direct cleavage of the C-21/C-22 double bond. 27 was transformed into the oximes 37-42 and by Wittig reaction to (21Z)-thiangazole (43) and analogues 44-46 with proton and alkyl residues replacing phenyl. 21,22-Didehydrothiangazole (50) was synthesized in a multi-step reaction from 27 via the 20-alkinyl intermediate 49. The insecticidal activities and inhibition of the respiratory chain (complex I) by the thiangazole analogues were determined and compared with the natural product.Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2046/1999/99007_s.pdf or from the author.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
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