Synthesis and Biological Evaluation of Novel 2-(4-acetyl-3-methyl- 5-(arylamino) thiophen-2-yl)-3-arylquinazolin-4(3H)-one Derivatives as Potential Anti-inflammatory and Antioxidant Agents

Author(s): Priyanka S. Chaudhari* , Sohan S. Chitlange , Rabindra K. Nanda .

Journal Name: Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry

Volume 17 , Issue 2 , 2018

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Graphical Abstract:


Background: A new series of 2-(4-acetyl-3-methyl-5-(arylamino) thiophen-2- yl)-3-arylquinazolin-4(3H)-one derivatives (11a-11j) were synthesized from acetyl acetone, phenyl isothiocyanate and 2-chloromethyl quinazolinone.

Objective: Due to side effects of Non Steroidal Anti-Inflammatory Drugs (NSAID), an attempt was made to identify the novel tetrasubstituted thiophene lead compound as potential anti-inflammatory and antioxidant agent.

Methods: Then newly synthesized compounds were characterized by IR spectroscopy, 1H NMR and mass spectrometry. The synthesized compounds were screened for their in vivo anti-inflammatory activity in carrageenan-induced rat hind paw edema model at dose 20mg/kg body weight using diclofenac sodium as a standard drug. The compounds were also evaluated for their in vitro DPPH free radical-scavenging activity and nitric oxide radical scavenging activity at the concentrations of 10, 20, 40, 60, 80 and 100 µg/mL using ascorbic acid as standard drug.

Results: The results from carrageenan-induced rat hind paw edema showed that compounds 11e, 11f and 11b show a significant anti-inflammatory activity of 46.61%, 48.94% and 47.04 % protection respectively to inflamed paw but less than diclofenac sodium. Compounds 11h and 11e show good DPPH free radical scavenging and nitric oxide radical scavenging activity, respectively.

Conclusion: From results, it was observed that highly substituted thiophene scaffold exhibits anti-inflammatory and antioxidant activity.

Keywords: Anti-inflammatory activity, antioxidant activity, tetrasubstituted thiophene, inflammation, COX, PGs.

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Article Details

Year: 2018
Page: [102 - 114]
Pages: 13
DOI: 10.2174/1871523017666180910105609

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