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Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant

Vasorelaxant is the common drug used for the treatment of hypertensive emergencies. The most widely studied stilbenoid, namely resveratrol (RV) was reported its ability to induce vasorelaxation through numerous signalling pathways on the blood vessel membrane. In this study, the tri-ethoxy (SB 1a-7a...

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Main Author: Chan, Sock Ying
Format: Thesis
Language:English
Published: 2021
Subjects:
QD1-999 Chemistry
Online Access:http://eprints.usm.my/55076/1/CHAN%20SOCK%20YING%20-%20TESIS.pdf
http://eprints.usm.my/55076/
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spelling my.usm.eprints.55076 http://eprints.usm.my/55076/ Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant Chan, Sock Ying QD1-999 Chemistry Vasorelaxant is the common drug used for the treatment of hypertensive emergencies. The most widely studied stilbenoid, namely resveratrol (RV) was reported its ability to induce vasorelaxation through numerous signalling pathways on the blood vessel membrane. In this study, the tri-ethoxy (SB 1a-7a), tetra-methoxy (SB 8a-13a) and di-methoxy (SB 14-16) stilbene derivatives were successfully synthesized via the conventional Wittig reaction wherein the A- and B- rings of the stilbene backbone were formed from the synthesized phosphonium salts and commercially available substituted benzaldehydes, respectively. The trans- (E) isomers were isolated and purified. The hydroxylated stilbenes (SB 1b, SB 3b-4b, SB 6b-8b and SB 11b-13b) were further synthesized from the alkoxylated stilbenes via poly O-dealkylation approach employing the modified aluminium trichloride/N,N-dimethylaniline system. All the synthesized SB compounds were elucidated by the FT-IR, 1D and 2D NMR spectroscopies. The in vitro vascular response of the synthesized SB compounds was primarily assessed on the phenylephrine (PE)-precontracted endothelium-intact isolated aortic rings of the male Sprague Dawley (SD) rats. SB 6b presented remarkable Rmax (95.11 ± 2.87 %) which was more than two-fold improvement of the vasorelaxation of the lead compound, RV (Rmax = 42.90 ± 1.67 %), suggesting the potency of SB 6b to be adopted as a new lead compound for drug optimization. The overall data illustrated the type, number and position of the substituents on the A- and B-rings were equally essential in triggering the vasorelaxation response. 2021-05 Thesis NonPeerReviewed application/pdf en http://eprints.usm.my/55076/1/CHAN%20SOCK%20YING%20-%20TESIS.pdf Chan, Sock Ying (2021) Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant. Masters thesis, Perpustakaan Hamzah Sendut.
institution Universiti Sains Malaysia
building Hamzah Sendut Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Sains Malaysia
content_source USM Institutional Repository
url_provider http://eprints.usm.my/
language English
topic QD1-999 Chemistry
spellingShingle QD1-999 Chemistry
Chan, Sock Ying
Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant
description Vasorelaxant is the common drug used for the treatment of hypertensive emergencies. The most widely studied stilbenoid, namely resveratrol (RV) was reported its ability to induce vasorelaxation through numerous signalling pathways on the blood vessel membrane. In this study, the tri-ethoxy (SB 1a-7a), tetra-methoxy (SB 8a-13a) and di-methoxy (SB 14-16) stilbene derivatives were successfully synthesized via the conventional Wittig reaction wherein the A- and B- rings of the stilbene backbone were formed from the synthesized phosphonium salts and commercially available substituted benzaldehydes, respectively. The trans- (E) isomers were isolated and purified. The hydroxylated stilbenes (SB 1b, SB 3b-4b, SB 6b-8b and SB 11b-13b) were further synthesized from the alkoxylated stilbenes via poly O-dealkylation approach employing the modified aluminium trichloride/N,N-dimethylaniline system. All the synthesized SB compounds were elucidated by the FT-IR, 1D and 2D NMR spectroscopies. The in vitro vascular response of the synthesized SB compounds was primarily assessed on the phenylephrine (PE)-precontracted endothelium-intact isolated aortic rings of the male Sprague Dawley (SD) rats. SB 6b presented remarkable Rmax (95.11 ± 2.87 %) which was more than two-fold improvement of the vasorelaxation of the lead compound, RV (Rmax = 42.90 ± 1.67 %), suggesting the potency of SB 6b to be adopted as a new lead compound for drug optimization. The overall data illustrated the type, number and position of the substituents on the A- and B-rings were equally essential in triggering the vasorelaxation response.
format Thesis
author Chan, Sock Ying
author_facet Chan, Sock Ying
author_sort Chan, Sock Ying
title Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant
title_short Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant
title_full Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant
title_fullStr Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant
title_full_unstemmed Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant
title_sort synthesis, characterization and in vitro potency of di-, tri-, and tetra-substituted stilbene derivatives as vasorelaxant
publishDate 2021
url http://eprints.usm.my/55076/1/CHAN%20SOCK%20YING%20-%20TESIS.pdf
http://eprints.usm.my/55076/
_version_ 1746211083480203264
score 13.244368

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