Bengamide derivatives, method for the production thereof and use thereof for the treatment of cancer

Preparation of bengamide compounds (3-alkenoylamino-hexahydroazepin-2-one derivatives) (A) involves fermenting Myxococcus virescens ST200611 (DSM 15898) (or its variants and/or mutants). Some of the bengamide derivatives (A) (i.e. 3-(2-methoxy-8-methyl-3,4,5-trihydroxydec-6E-enoylamino-hexahydroazep...

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Bibliographische Detailangaben
Hauptverfasser: HOLGER HOFFMANN, SABINE HAAG-RICHTER, HEIKO TIETGEN, MICHAEL KURZ
Format: Patent
Sprache:eng
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Zusammenfassung:Preparation of bengamide compounds (3-alkenoylamino-hexahydroazepin-2-one derivatives) (A) involves fermenting Myxococcus virescens ST200611 (DSM 15898) (or its variants and/or mutants). Some of the bengamide derivatives (A) (i.e. 3-(2-methoxy-8-methyl-3,4,5-trihydroxydec-6E-enoylamino-hexahydroazepin-2-ones) are new. Preparation of bengamide compounds of formula (A) or their salts involves fermenting Myxococcus virescens ST200611 (DSM 15898) (or its variants and/or mutants) in a culture medium, isolating the obtained (A) from the culture medium and optionally derivatizing and/or salifying the product. [Image] R 1H or 1-6C alkyl; R 2H or OH; R 3H or 2-7C alkanoyl; R 4Me or Et. Independent claims are included for: (1) bengamide derivatives of formula (B) (this is structure (A) where R 4 = Et) and their salts as new compounds; (2) the new microorganism Myxococcus virescens ST200611 (DSM 15898); and (3) the use of Myxococcus virescens ST200611 (DSM 15898) (or its variants and/or mutants) for the production of (A). ACTIVITY : Cytostatic. A specific diastereomer of 3-(2-methoxy-8-methyl-3,4,5-trihydroxydec-6E-enoylamino)-hexahydroazepin-2-one (A1) had TC 5 0 values of 6 mu M and 10 mu M for inhibition of proliferation of Hep-G2 and Colo 205 cells respectively. MECHANISM OF ACTION : Mitosis inhibitor; Cell cycle regulator.