Journal article Open Access

SYNTHESIS, SPECTRAL CHARACTERIZATION OF DIBENZOFURAN-1,3-THIAZOLE CARBOXAMIDE DERIVATIVES AND EVALUATED FOR ANTI-INFLAMMATORY POTENTIAL

Vinit Mishra, Alok Pal Jain, Amit Nayak*


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    <subfield code="a">SYNTHESIS, SPECTRAL CHARACTERIZATION OF DIBENZOFURAN-1,3-THIAZOLE CARBOXAMIDE DERIVATIVES AND EVALUATED FOR ANTI-INFLAMMATORY POTENTIAL</subfield>
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    <subfield code="a">&lt;p&gt;&lt;strong&gt;&lt;em&gt;Objective:&lt;/em&gt;&lt;/strong&gt;&lt;em&gt; The objective of the paper is synthesis and characterization of dibenzofuran-1,3-thiazole carboxamide derivatives and screened for anti-inflammatory potential&lt;/em&gt;&lt;/p&gt;

&lt;p&gt;&lt;strong&gt;&lt;em&gt;Material and methods:&lt;/em&gt;&lt;/strong&gt;&lt;em&gt; The present work was aimed to synthesis some dibenzofuran-1,3 thiazole carboxamide derivatives by four step reactions with the substitution of various substituted benzylamine under suitable catalyst. The compound 1 (S-((4-chlorodibenzo[b,d]furan-1-yl)methyl)thiohydroxylamine), Compound 2 (ethyl 2-(4-chlorodibenzo[b,d]furan-1-yl)-5-methylthiazole-4-carboxylate), compound 3 (2-(4-chlorodibenzo[b,d]furan-1-yl)-5-methylthiazole-4-carboxylic acid) and compound 4 (N-benzyl-2-(4-chlorodibenzo[b,d]furan-1-yl)-5-methyl thiazole-4-carboxamide) were prepared. The Compound 4 coded as compound TC-1 to TC-14. In this four steps process total 12 compounds have been synthesized and evaluated for the anti-inflammatory potential by protein denaturation assay.&lt;/em&gt;&lt;/p&gt;

&lt;p&gt;&lt;strong&gt;&lt;em&gt;Result and Discussion:&lt;/em&gt;&lt;/strong&gt;&lt;em&gt; &amp;nbsp;The IR spectrum of the compounds has shown the characteristics peak (cm&lt;sup&gt;-1&lt;/sup&gt;) of&lt;/em&gt;&lt;em&gt; N-H at 3412; C=C-H at 3470; C=O at 1735; C=C at 1624&amp;ndash;1446; C-N at 1015; &lt;/em&gt;&lt;em&gt;p-substitution at &lt;/em&gt;&lt;em&gt;792&lt;/em&gt;&lt;em&gt;; C-F at 1102&lt;/em&gt;&lt;strong&gt;&lt;em&gt;; &lt;/em&gt;&lt;/strong&gt;&lt;em&gt;C-Cl at 855; C-Br at 1015; &lt;/em&gt;&lt;em&gt;N-O at 1356; N=O at 1558. The 1HNMR spectra of Final compounds (TC-1 to TC-12) depicted the peak at &lt;/em&gt;&lt;em&gt;2.90 (3H, CH&lt;sub&gt;3&lt;/sub&gt;); 4.64 - 4.65 (2H, CH&lt;sub&gt;2&lt;/sub&gt;); 7.05-7.10 (2H, Ar-H); 7.35 (1H, Ar-H); 7.33 &amp;ndash; 7.39 (4H, Ar-H); 7.45 (1H, Ar-H); 7.48 - 7.50 (1H, Ar-H); 7.62 - 7.63 (1H, Ar-H); 7.90 - 7.92 (1H, Ar-H); 8.38 &amp;ndash; 8.40 (1H, N-H).&lt;/em&gt;&lt;em&gt; Compound TC-1, mass spectrum has shown peak at m/z = 450.85, which matches the chemical formula C&lt;sub&gt;24&lt;/sub&gt;H&lt;sub&gt;16&lt;/sub&gt;ClFN&lt;sub&gt;2&lt;/sub&gt;O&lt;sub&gt;2&lt;/sub&gt;S. The protein denaturation assay of synthesized compound stated that most active compound are TC-1, TC-2, TC-3, TC-4 and TC-5 and compounds TC-7 &amp;amp; TC-9 has shown the mild activity and compound TC-6, TC-8, TC-10, TC-11 and TC-12 has shown modest activity.&amp;nbsp; &lt;/em&gt;&lt;/p&gt;

&lt;p&gt;&lt;strong&gt;&lt;em&gt;Conclusion&lt;/em&gt;&lt;/strong&gt;&lt;em&gt;: The &lt;/em&gt;&lt;em&gt;Cl, Br, I, NO&lt;sub&gt;2&lt;/sub&gt; and F substitution enhance the activity when it attached to 4-position of the thiazole ring with addition of electronegative atom also enhance the anti-inflammatory potential of compounds&lt;/em&gt;&lt;em&gt;.&lt;/em&gt;&lt;/p&gt;

&lt;p&gt;&lt;strong&gt;Keywords&lt;/strong&gt;: &lt;em&gt;Anti-inflammatory, thiazole, protein denaturation assay, dibenzofuran&lt;/em&gt;&lt;/p&gt;</subfield>
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