Total Synthesis and Biological Evaluation of Mutolide and Analogues

Total Synthesis and Biological Evaluation of Mutolide and Analogues

The convergent total syntheses of three 14-membered macrolide natural products, mutolide, nigrosporolide and (4S,7S,13S)-4,7-dihydroxy-13-tetradeca-2,5,8-trienolide have been achieved. The key synthetic features include Shiina macrolactonization to assemble the 14-membered macrocyclic core, Wittig o...

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Main Author: Thiraporn A.
Other Authors: Mahidol University
Format: Article
Published: 2023
Subjects:
Biochemistry, Genetics and Molecular Biology
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/83633
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spelling th-mahidol.836332023-06-18T23:45:48Z Total Synthesis and Biological Evaluation of Mutolide and Analogues Thiraporn A. Mahidol University Biochemistry, Genetics and Molecular Biology The convergent total syntheses of three 14-membered macrolide natural products, mutolide, nigrosporolide and (4S,7S,13S)-4,7-dihydroxy-13-tetradeca-2,5,8-trienolide have been achieved. The key synthetic features include Shiina macrolactonization to assemble the 14-membered macrocyclic core, Wittig or Still-Gennari olefination and selective reduction of propargylic alcohol to construct the E- or Z-olefins. Cross metathesis was also highlighted as an efficient tool to forge the formation of E-olefin. The three synthetic macrolides were evaluated for their cytotoxic activity against three human cancer cell lines as well as for inhibitory effect on CFTR-mediated chloride secretion in human intestinal epithelial (T84) cells. Mutolide displayed significant cytotoxic activity against HCT116 colon cancer cells with an IC50 of ∼12 μM as well as a potent CTFR inhibitory effect with an IC50 value of ∼1 μM. 2023-06-18T16:45:48Z 2023-06-18T16:45:48Z 2022-08-15 Article Chemistry - An Asian Journal Vol.17 No.16 (2022) 10.1002/asia.202200329 1861471X 18614728 35727893 2-s2.0-85133473062 https://repository.li.mahidol.ac.th/handle/123456789/83633 SCOPUS
institution Mahidol University
building Mahidol University Library
continent Asia
country Thailand
Thailand
content_provider Mahidol University Library
collection Mahidol University Institutional Repository
topic Biochemistry, Genetics and Molecular Biology
spellingShingle Biochemistry, Genetics and Molecular Biology
Thiraporn A.
Total Synthesis and Biological Evaluation of Mutolide and Analogues
description The convergent total syntheses of three 14-membered macrolide natural products, mutolide, nigrosporolide and (4S,7S,13S)-4,7-dihydroxy-13-tetradeca-2,5,8-trienolide have been achieved. The key synthetic features include Shiina macrolactonization to assemble the 14-membered macrocyclic core, Wittig or Still-Gennari olefination and selective reduction of propargylic alcohol to construct the E- or Z-olefins. Cross metathesis was also highlighted as an efficient tool to forge the formation of E-olefin. The three synthetic macrolides were evaluated for their cytotoxic activity against three human cancer cell lines as well as for inhibitory effect on CFTR-mediated chloride secretion in human intestinal epithelial (T84) cells. Mutolide displayed significant cytotoxic activity against HCT116 colon cancer cells with an IC50 of ∼12 μM as well as a potent CTFR inhibitory effect with an IC50 value of ∼1 μM.
author2 Mahidol University
author_facet Mahidol University
Thiraporn A.
format Article
author Thiraporn A.
author_sort Thiraporn A.
title Total Synthesis and Biological Evaluation of Mutolide and Analogues
title_short Total Synthesis and Biological Evaluation of Mutolide and Analogues
title_full Total Synthesis and Biological Evaluation of Mutolide and Analogues
title_fullStr Total Synthesis and Biological Evaluation of Mutolide and Analogues
title_full_unstemmed Total Synthesis and Biological Evaluation of Mutolide and Analogues
title_sort total synthesis and biological evaluation of mutolide and analogues
publishDate 2023
url https://repository.li.mahidol.ac.th/handle/123456789/83633
_version_ 1781415197164961792

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