ISSN:
1434-193X
Keywords:
β-Methoxyacrylates
;
Melithiazols
;
Myxobacteria
;
Natural products
;
Fungicides
;
Structure-activity relationships
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
From cultures of Melittangium lichenicola, Archangium gephyra and Myxococcus stipitatus, thirteen new β-methoxyacrylate (MOA) fungicides related to myxothiazols (1) have been isolated. Melithiazols A (2a), D (2b), K (2c), and L (2d) are characterized by a thiazoline-thiazole system, whereas melithiazols B (3a), E (3b), F (3c), G (3d), H (3e), I (3f), M (3g), and N (3h) are bis(thiazoles). Melithiazol C (4), as the first representative of this class of compounds, contains only one thiazole ring. The structures were established on the basis of spectroscopic data, and confirmed in the case of melithiazol E (3b), including its relative configuration, by an X-ray structure analysis. The absolute configuration of melithiazols A (2a) and B (3a) was determined by degradation and CD spectroscopy. Antifungal and cytotoxic activities, inhibition of NADH oxidation, and lipophilicities of melithiazols 2-4, myxothiazols 1, and strobilurin-type compounds are compared.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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