Cyclamenols E and F, two diastereoisomeric bicyclic macrolactams with a cyclopentane moiety from an Antarctic Streptomyces species

Literature Information

Publication Date 2019-12-02
DOI 10.1039/C9QO01215J
Impact Factor 5.281
Authors

Hao Chen


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Abstract

Cyclamenols E (1) and F (2), two bicyclic macrolactams possessing a cyclopentane moiety, were isolated from the Antarctic Streptomyces sp. OUCMDZ-4348. Their structures, including absolute configurations, were determined by spectroscopic analysis, chemical derivatization, and ECD calculation. Treatment of compound 1 with 2,2-dimethoxypropane and pyridinium p-toluenesulfonate in acetone/DMF led to the formation of acetonide 1a with an unexpected skeleton. Compound 1 showed moderate inhibitory activity against the gastric carcinoma cell line N87 with an IC50 value of 9.8 μM, but no cytotoxicity was observed on the other 25 cancer cell lines tested.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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