{"title":"Synthesis and Structure-Activity Relationship Studies of Truncated Artificial Analogues of Amphidinol 3.","authors":"Yoko Yasuno, Yuma Wakamiya, Yusuke Mita, Yuki Yamashita, Nobuaki Matsumori, Tohru Oishi","doi":"10.1002/asia.70353","DOIUrl":null,"url":null,"abstract":"<p><p>Structure-activity relationship studies of artificial analogues of amphidinol 3 (AM3) were conducted. Based on the truncated molecule corresponding to the C21-C67 section of AM3, which elicited comparable antifungal activity to the parent compound, its stereoisomers were synthesized from polyol, bis-THP, and polyene units via Suzuki-Miyaura coupling and Julia-Kocienski olefination. Variants at both polyol and polyene termini were also synthesized. Evaluation of the antifungal activity of the analogues revealed the importance of the stereochemistry of the bis-THP core, which is a conserved region among amphidinol congeners. In addition, structural differences of the polyene terminus highly affected the antifungal activity in the case of the truncated analogues, contrary to the naturally occurring congeners. The C22-C67 analogue, only one-carbon shorter at the polyol terminus, elicited no antifungal activity. Therefore, the minimum structure to elicit antifungal activity was elucidated to be the C21-C67 section of AM3.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e70353"},"PeriodicalIF":3.3000,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.70353","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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Abstract
Structure-activity relationship studies of artificial analogues of amphidinol 3 (AM3) were conducted. Based on the truncated molecule corresponding to the C21-C67 section of AM3, which elicited comparable antifungal activity to the parent compound, its stereoisomers were synthesized from polyol, bis-THP, and polyene units via Suzuki-Miyaura coupling and Julia-Kocienski olefination. Variants at both polyol and polyene termini were also synthesized. Evaluation of the antifungal activity of the analogues revealed the importance of the stereochemistry of the bis-THP core, which is a conserved region among amphidinol congeners. In addition, structural differences of the polyene terminus highly affected the antifungal activity in the case of the truncated analogues, contrary to the naturally occurring congeners. The C22-C67 analogue, only one-carbon shorter at the polyol terminus, elicited no antifungal activity. Therefore, the minimum structure to elicit antifungal activity was elucidated to be the C21-C67 section of AM3.
期刊介绍：
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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