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Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B

A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A (1) and B (2), recently isolated from Ficus schwarzii, is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the...

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Main Authors: Lee, Fong-Kai, Krishnan, Premanand, Muhamad, Azira, Low, Yun-Yee, Kam, Toh-Seok, Ting, Kang-Nee, Lim, Kuan-Hon
Format: Article
Published: Taylor & Francis 2022
Subjects:
QD Chemistry
Online Access:http://eprints.um.edu.my/41830/
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spelling my.um.eprints.418302023-10-20T04:48:32Z http://eprints.um.edu.my/41830/ Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B Lee, Fong-Kai Krishnan, Premanand Muhamad, Azira Low, Yun-Yee Kam, Toh-Seok Ting, Kang-Nee Lim, Kuan-Hon QD Chemistry A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A (1) and B (2), recently isolated from Ficus schwarzii, is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the core skeleton of the target compounds. The overall synthetic yields of 1 and 2 were 9.1% and 3.5%, respectively. Synthetic (-)-1, (+)-1 and (+/-)-1 exhibited comparable vasorelaxation as natural schwarzinicine A on rat isolated aortic rings, suggesting that the observed vasorelaxant effects were not influenced by the chirality at C-2. Taylor & Francis 2022-08-01 Article PeerReviewed Lee, Fong-Kai and Krishnan, Premanand and Muhamad, Azira and Low, Yun-Yee and Kam, Toh-Seok and Ting, Kang-Nee and Lim, Kuan-Hon (2022) Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B. Natural Product Research, 36 (15). pp. 3972-3978. ISSN 1478-6419, DOI https://doi.org/10.1080/14786419.2021.1903005 <https://doi.org/10.1080/14786419.2021.1903005>. 10.1080/14786419.2021.1903005
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QD Chemistry
spellingShingle QD Chemistry
Lee, Fong-Kai
Krishnan, Premanand
Muhamad, Azira
Low, Yun-Yee
Kam, Toh-Seok
Ting, Kang-Nee
Lim, Kuan-Hon
Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B
description A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A (1) and B (2), recently isolated from Ficus schwarzii, is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the core skeleton of the target compounds. The overall synthetic yields of 1 and 2 were 9.1% and 3.5%, respectively. Synthetic (-)-1, (+)-1 and (+/-)-1 exhibited comparable vasorelaxation as natural schwarzinicine A on rat isolated aortic rings, suggesting that the observed vasorelaxant effects were not influenced by the chirality at C-2.
format Article
author Lee, Fong-Kai
Krishnan, Premanand
Muhamad, Azira
Low, Yun-Yee
Kam, Toh-Seok
Ting, Kang-Nee
Lim, Kuan-Hon
author_facet Lee, Fong-Kai
Krishnan, Premanand
Muhamad, Azira
Low, Yun-Yee
Kam, Toh-Seok
Ting, Kang-Nee
Lim, Kuan-Hon
author_sort Lee, Fong-Kai
title Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B
title_short Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B
title_full Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B
title_fullStr Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B
title_full_unstemmed Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B
title_sort concise synthesis of the vasorelaxant alkaloids schwarzinicines a and b
publisher Taylor & Francis
publishDate 2022
url http://eprints.um.edu.my/41830/
_version_ 1781704561596039168
score 13.214268

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