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SYNTHESIS, CHARACTERIZATION AND ANTICANCER SCREENING OF NEW SULFONAMIDE-THIAZOLE DERIVED ACETAMIDE COMPOUNDS

Surendra Singh, Alok Pal Jain, Amit Nayak


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  <identifier identifierType="DOI">10.5281/zenodo.6798448</identifier>
  <creators>
    <creator>
      <creatorName>Surendra Singh, Alok Pal Jain, Amit Nayak</creatorName>
    </creator>
  </creators>
  <titles>
    <title>SYNTHESIS, CHARACTERIZATION AND ANTICANCER SCREENING OF NEW SULFONAMIDE-THIAZOLE DERIVED ACETAMIDE COMPOUNDS</title>
  </titles>
  <publisher>Zenodo</publisher>
  <publicationYear>2022</publicationYear>
  <dates>
    <date dateType="Issued">2022-07-05</date>
  </dates>
  <resourceType resourceTypeGeneral="JournalArticle"/>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://zenodo.org/record/6798448</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsVersionOf">10.5281/zenodo.6798447</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="https://creativecommons.org/licenses/by/4.0/legalcode">Creative Commons Attribution 4.0 International</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">&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 sulfonamide-thiazole derived acetamide derivatives and evaluated for t&lt;em&gt;hem for the anticancer potential.&lt;/em&gt;&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 sulfonamide-thiazole derived acetamide derivatives has been prepared by the two step process, in first step, 2-chloro-N-(4-((2,3-dihydro-4H-1,4-oxazin-4-yl)sulfonyl)phenyl) acetamide (&lt;strong&gt;Compound 2&lt;/strong&gt;) was synthesized, and in step 2, N-(4-((2,3-dihydro-4H-1,4-oxazin-4-yl)sulfonyl)phenyl)-2-((4-substitutedthiazol-2-yl)amino)acet-amide &lt;strong&gt;(Compound 3)&lt;/strong&gt; was synthesized by the reaction of synthesized compound 2 with different 4-substituted thiazol-2-amine to from the final compounds &lt;strong&gt;(compound 3)&lt;/strong&gt;. Total eleven compounds have been synthesized and characterized by physicochemical and IR, NMR and MASS spectral analysis. The final compounds (SA-1 to SA-11) have been evaluated for anticancer activity by SRB assay method.&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; The IR spectrum of the compounds (SA-1 to SA-11) has shown the characteristics peak (cm&lt;sup&gt;-1&lt;/sup&gt;) of N-H peak at 3331, N-H peak at 3118, aromatic C-H peak at 3039, C=O peak at 1672, C-H aliphatic peak at 2938, C-Cl peak at 850, C-Br peak at 1018, C-F peak at 1102, N-O peak at 1358 and N=O peak at 1562. The 1HNMR spectra depicted the&amp;nbsp;&amp;nbsp; peak of N-H at 10.25 ppm, Thiazole-H peak at 6.25 ppm, CH2 peak at 4.19. The 13CNMR spectrum denotes the peak in ppm of C=O at 170.5, C=N at 162.3 and CH2 at 45.6. Compound SA-1, mass spectrum has shown peak at m/z = 414.02, which matches the chemical formula C&lt;sub&gt;15&lt;/sub&gt;H&lt;sub&gt;15&lt;/sub&gt;ClN&lt;sub&gt;4&lt;/sub&gt;O&lt;sub&gt;4&lt;/sub&gt;S&lt;sub&gt;2&lt;/sub&gt;. The result data of the synthesized compounds by SRB assay stated the IC50 value of compounds SA-1 (7.7), SA-3 (9.5), SA-4 (14.7) and SA-11 (8.1) has shown better activity as compared to the standard drug paclitaxel (31.1)&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, NO&lt;sub&gt;2&lt;/sub&gt; and F compounds enhance the activity when it attached to 4-position of the thiazole ring as well as presence of sulfonamide bearing thiazole with addition to electronegative atom enhance the anticancer activity of compounds&lt;/em&gt;&lt;/p&gt;

&lt;p&gt;&lt;strong&gt;Keywords: &lt;/strong&gt;&lt;em&gt;Anticancer activity, thiazole, sulfonamide, SRB assay, acetamide &lt;/em&gt;&lt;/p&gt;</description>
  </descriptions>
</resource>
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