Synthesis of E-stilbens as Potent Cyclooxygenase-2 Inhibitors and Identification of their Photochemical Products

Bekhradnia, Ahmad Reza and AhmadianMoghadam, Maryam and Tatar, Monire (2014) Synthesis of E-stilbens as Potent Cyclooxygenase-2 Inhibitors and Identification of their Photochemical Products. Journal of Mazandaran University of Medical Sciences, 24 (119). pp. 199-205.

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Official URL: http://jmums.mazums.ac.ir/article-1-4758-en.html

Abstract

Background and purpose: 1,2 diarylethylene or stilbenes are hydrocarbon derivatives with two phenyl group bonded to the double bond carbons. There are two isomers of stilbenes that Z-isomer is less stable than E-isomer. However, the Z-isomer is stronger than E-isomer as potent cyclooxygenase-2 (COX-2) inhibitor. E and Z isomers are interconverted through photochemical irradiation. In this research, Z-isomer was converted to E-isomer by irradiation in photoreactor that could be used as COX-2 inhibitor. Materials and methods: The reaction of p-bromothiophenol with dimethyl lsulfate in an aqueous sodium hydroxide solution produced p-bromothioanisole. Mentioned product was reacted with 4-x-styrene via Heck olefination. The olefination was performed with Bu4N+Cl-, LiOAc and LiCl in the presence of Pd (II) as a catalyst in DMF. E-1,2 diarylethylene derivatives were irradiated in photo-reactor and their photochemical products were isolated after irradiating by column chromatography. Results: 1,2�diarylstilbene derivatives were produced and their chemical structure were evaluated by 1H-NMR and IR spectroscopy. UV-vis absorption spectra were measured for all compounds before and after radiation. The photochemical product was isolated and identified Conclusion: E�diarylestilbenes were produced in the presence of Pd (II) and converted to more important Z-isomer by irradiation in photo-reactor

Item Type: Article
Uncontrolled Keywords: 1,2 diarylstilbene, photoisomerization, photochemical reaction
Depositing User: Unnamed user with email eprints@mazums.ac.ir
Date Deposited: 04 Jan 2018 15:20
Last Modified: 04 Jan 2018 15:20
URI: http://eprints.mazums.ac.ir/id/eprint/998

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