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
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spelling	my-usm-ep.550762022-10-03T03:59:27Z Synthesis, Characterization And In Vitro Potency Of Di-, Tri-, And Tetra-Substituted Stilbene Derivatives As Vasorelaxant 2021-05 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 http://eprints.usm.my/55076/ http://eprints.usm.my/55076/1/CHAN%20SOCK%20YING%20-%20TESIS.pdf application/pdf en public masters Perpustakaan Hamzah Sendut Pusat Pengajian Sains Kimia
institution	Universiti Sains Malaysia
collection	USM Institutional Repository
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
qualification_level	Master's degree
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
granting_institution	Perpustakaan Hamzah Sendut
granting_department	Pusat Pengajian Sains Kimia
publishDate	2021
url	http://eprints.usm.my/55076/1/CHAN%20SOCK%20YING%20-%20TESIS.pdf
_version_	1747822311064469504

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

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