trans-Stilbene C-Glycosides: Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity

Kalyana Kumar Ponnapalli; Avijit Kumar Adak; Anindya Das; Jen Shin Song; Szu Huei Wu; Chung-Ming Sun; Chun Cheng Lin

doi:10.1002/ajoc.201700148

trans-Stilbene C-Glycosides: Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity

Kalyana Kumar Ponnapalli, Avijit Kumar Adak, Anindya Das, Jen Shin Song, Szu Huei Wu, Chung-Ming Sun, Chun Cheng Lin^*

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摘要

A protocol for the microwave-assisted Heck coupling reaction of C-aryl glycosides and styrenes has been developed for the synthesis of mono- and bis(C-glycoside) stilbenes. This method exclusively provides C-glycoside trans-stilbenes in good yields. The Pd-catalyzed Heck coupling reaction was successfully applied to various functionalized C-glycosyl aryl iodides and various substituted styrenes to deliver several C-glycoside trans-stilbenes with high selectivity. The obtained C-glycosyl trans-stilbenes were also examined for human SGLT-2 inhibitory activity.

原文	English
頁（從 - 到）	1308-1321
頁數	14
期刊	Asian Journal of Organic Chemistry
卷	6
發行號	9
DOIs	https://doi.org/10.1002/ajoc.201700148
出版狀態	Published - 1 9月 2017

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title = "trans-Stilbene C-Glycosides: Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity",

abstract = "A protocol for the microwave-assisted Heck coupling reaction of C-aryl glycosides and styrenes has been developed for the synthesis of mono- and bis(C-glycoside) stilbenes. This method exclusively provides C-glycoside trans-stilbenes in good yields. The Pd-catalyzed Heck coupling reaction was successfully applied to various functionalized C-glycosyl aryl iodides and various substituted styrenes to deliver several C-glycoside trans-stilbenes with high selectivity. The obtained C-glycosyl trans-stilbenes were also examined for human SGLT-2 inhibitory activity.",

keywords = "cross-coupling, glycosylation, inhibitors, microwave chemistry, palladium",

author = "{Kumar Ponnapalli}, Kalyana and {Kumar Adak}, Avijit and Anindya Das and Song, {Jen Shin} and Wu, {Szu Huei} and Chung-Ming Sun and Lin, {Chun Cheng}",

year = "2017",

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doi = "10.1002/ajoc.201700148",

language = "English",

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T2 - Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity

AU - Kumar Ponnapalli, Kalyana

AU - Kumar Adak, Avijit

AU - Das, Anindya

AU - Song, Jen Shin

AU - Wu, Szu Huei

AU - Sun, Chung-Ming

AU - Lin, Chun Cheng

PY - 2017/9/1

Y1 - 2017/9/1

N2 - A protocol for the microwave-assisted Heck coupling reaction of C-aryl glycosides and styrenes has been developed for the synthesis of mono- and bis(C-glycoside) stilbenes. This method exclusively provides C-glycoside trans-stilbenes in good yields. The Pd-catalyzed Heck coupling reaction was successfully applied to various functionalized C-glycosyl aryl iodides and various substituted styrenes to deliver several C-glycoside trans-stilbenes with high selectivity. The obtained C-glycosyl trans-stilbenes were also examined for human SGLT-2 inhibitory activity.

AB - A protocol for the microwave-assisted Heck coupling reaction of C-aryl glycosides and styrenes has been developed for the synthesis of mono- and bis(C-glycoside) stilbenes. This method exclusively provides C-glycoside trans-stilbenes in good yields. The Pd-catalyzed Heck coupling reaction was successfully applied to various functionalized C-glycosyl aryl iodides and various substituted styrenes to deliver several C-glycoside trans-stilbenes with high selectivity. The obtained C-glycosyl trans-stilbenes were also examined for human SGLT-2 inhibitory activity.

KW - cross-coupling

KW - glycosylation

KW - inhibitors

KW - microwave chemistry

KW - palladium

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U2 - 10.1002/ajoc.201700148

DO - 10.1002/ajoc.201700148

M3 - Article

AN - SCOPUS:85020547965

SN - 2193-5807

VL - 6

SP - 1308

EP - 1321

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 9

ER -

trans-Stilbene C-Glycosides: Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity

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