SYNTHESIS OF 3,4-DIARYL-4-THIAZOLINE-2-THIONE DERIVATIVES AS NEW POTENTIAL COX-2 INHIBITORS

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EMAMI S.

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Journal: Journal of Mazandaran University of Medical Sciences Year:2007 | Volume:16 | Issue:56 Page(s): 60-67

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Title

SYNTHESIS OF 3,4-DIARYL-4-THIAZOLINE-2-THIONE DERIVATIVES AS NEW POTENTIAL COX-2 INHIBITORS

Author(s)

EMAMI S. | Issue Writer Certificate

Keywords

SYNTHESISQ2

ANTI-INFLAMMATORY DRUGSQ3

COX-2 INHIBITORSQ3

4-THIAZOLINE-2-THIONEQ3

Abstract

Background and purpose: Nonsteroidal ANTI-INFLAMMATORY DRUGS (NSAIDs) remain among the most widely prescribed drugs worldwide for the treatment of inflammation including pain-releasing, anti-pyretic and rheumatoid arthritis. The conventional NSAIDs exert their effects by inhibiting cyclooxygenase (COX) enzymes. Subsequent research and rational drug design validated the initial concept that a selective COX-2 inhibitor would illicit effective anti-inflammatory without the adverse ulcerogenic effect associated with the use of NSAIDs that inhibit both COX-1 and COX-2. Accordingly, in this work we report the SYNTHESIS of a new diaryl heterocyclic series, the 3, 4-diaryl-4-thiazoline-2- thione, as potential selective COX-2 INHIBITORS.Materials and Methods: The starting material thioanisole underwent Friedel-Craft reaction with acetic acid in the presence of trifluoroacetic anhydride followed by oxidation by MCPBA to give 4- (methylsulfonyl) acetophenone. This compound was then treated with Br2 in CHCl3 to give phenacyl bromide derivative. On the other hand, condensation of aniline derivatives with carbon disulfide in the presence of triethylamine gave the corresponding dithiocarbamate salt. Subsequently, reaction of aryl dithiocarbamate with methylsulfonyl phenacyl bromide furnished cyclic alcohol intermediate, which was dehydrated by 80% H2SO4 to give 3, 4-diaryl-4-thiazoline-2-thione.Results: All of the target compounds were characterized by their 1H-NMR, 13C-NMR, IR and mass spectral data. Conclusion: In view of the pharmacological importance of the selective COX-2 INHIBITORS,a series of 3,4-diaryl-4-thiazoline-2-thiones having pharmacophoric features of COX-2 INHIBITORS have been synthesized via convenient and efficient synthetic pathway, and structurally characterized by different spectroscopic methods.

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APA: Copy

EMAMI, S.. (2007). SYNTHESIS OF 3,4-DIARYL-4-THIAZOLINE-2-THIONE DERIVATIVES AS NEW POTENTIAL COX-2 INHIBITORS. JOURNAL OF MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES, 16(56), 60-67. SID. https://sid.ir/paper/45631/en

Vancouver: Copy

EMAMI S.. SYNTHESIS OF 3,4-DIARYL-4-THIAZOLINE-2-THIONE DERIVATIVES AS NEW POTENTIAL COX-2 INHIBITORS. JOURNAL OF MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES[Internet]. 2007;16(56):60-67. Available from: https://sid.ir/paper/45631/en

IEEE: Copy

S. EMAMI, “SYNTHESIS OF 3,4-DIARYL-4-THIAZOLINE-2-THIONE DERIVATIVES AS NEW POTENTIAL COX-2 INHIBITORS,” JOURNAL OF MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES, vol. 16, no. 56, pp. 60–67, 2007, [Online]. Available: https://sid.ir/paper/45631/en

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