Synthesis of Some Novel 2-Azetidinones/4-Thiazolidinones Bearing 1, 3, 4- Thiadiazole Nucleus and Screening for its Anti-Imflammatory Activity

Author(s): B. Gowramma, T. K. Praveen, R. Kalirajan, B. Babu.

Journal Name: Letters in Drug Design & Discovery

Volume 13 , Issue 7 , 2016

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Graphical Abstract:


Objective: The objective of the study was to synthesize a series of 3-chloro-4-(substituted phenyl)-1-(5-styryl-1, 3, 4-thiladiazole-2-yl) azetidin-2-one / 2-(substituted phenyl)-3-(5-styryl-1, 3, 4- thiadiazole-2-yl)-thiazolidin-4-one and screened for their possible anti-inflammatory activity by carrageenan induced paw edema in rats.

Method: The synthesis of 2-amino-5-styryl-1, 3, 4-thiadiazole, an intermediate was carried out by oxidative cyclization method. In the current study, thiosemicarbazone (I) was subjected to oxidative cyclization using ferric chloride as an oxidising agent, to get 2- amino- 5- styryl -1, 3, 4-thiadiazole (II). Futhermore, compound (II) was reacted with different aromatic aldehydes in methanol to form N-(4-sustituted)- 5- styryl- 1, 3, 4-thiadiazol-2-amine (III a-h). Compound (III ah) was reacted with chloroacetyl chloride in triethylamine to form 2-azetidinone derivatives bearing 1, 3, 4-thiadiazole nucleus (IV a-h). Compound (III a-h) on cyclocondensation with mercaptoacetic acid leads to the formation of 4- thiazolidinone derivatives bearing 1, 3, 4-thiadiazole nucleus (V a-h).

Results: The synthesis of the targeted compounds IVa-h and Va-h was confirmed through their MP, IR, 1H-NMR and mass spectrum studies. Compounds IVa, IVb and IVc (56.32, 61.11 and 58.24 % inhibition) exhibited significant antiinflammatory activity than that of diclofenac (65.13% inhibition).

Conclusion: It may be concluded that the presence of methoxy, nitro and hydroxyl phenyl groups substituting 2- azetidinone bearing 1, 3, 4-thiadiazole showed significant anti-inflammatory activity.

Keywords: Anti-inflammatory activity, diclofenac, 2-Azetidinone, 4-Thiazolidinone, 1, 3, 4-Thiadiazole, carrageenan induced paw edema.

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Article Details

Year: 2016
Page: [676 - 683]
Pages: 8
DOI: 10.2174/1570180813666151123235546
Price: $65

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