Synthesis and biological activity of 2-azetidinones, sulphonamides, arylamides and thiourea derivatives

Abstract

2-Amino-4-[2-(<i style="mso-bidi-font-style:normal">p</i>-chlorobenzenesulphonamido)phenyl]thiazole <b style="mso-bidi-font-weight:normal">1</b> on condensation with aromatic aldehydes afford 2-benzalamino-4-[2-(<i style="mso-bidi-font-style:normal">p</i>- chlorobenzenesulphonamido)phenyl]thiazole of the type <b style="mso-bidi-font-weight: normal">2</b>. The latter undergoes cyclisation with chloroacetyl chloride in the presence of triethylamine furnishing 2-(4'-aryl-3'-chloro-2'-azetidinon-1'-yl)-4-[2-(<i style="mso-bidi-font-style: normal">p</i>-chlorobenzenesulphonamido)

<span style="font-size:12.0pt;font-family:" times="" new="" roman";="" mso-fareast-font-family:"times="" roman";mso-ansi-language:en-in;mso-fareast-language:="" en-in;mso-bidi-language:ar-sa"="" lang="EN-IN">Phenyl]thiazole <b style="mso-bidi-font-weight: normal">3</b>. Thiazole <b style="mso-bidi-font-weight:normal">1</b> on reaction with different arylsulphonyl chlorides, substituted benzoyl chlorides and various aryl isothiocyanates gives the corresponding 2-aryl sulphonamido-4-[2-(<i style="mso-bidi-font-style:normal">p</i>-chlorobenzene-sulphonamido)phenyl]thiazoles <b style="mso-bidi-font-weight:normal">4</b>, 2-aroylamino-4-[2-(<i style="mso-bidi-font-style:normal">p</i>-chlorobenzenesulphonamido)phenyl]thiazoles <b style="mso-bidi-font-weight:normal">5</b> and 2- substituted arylthioureidoamino-4-[2-(<i style="mso-bidi-font-style:normal">p</i>-chlorobenzene-sulphonamido)phenyl]thiazoles <b style="mso-bidi-font-weight:normal">6</b>. The products display moderate to good antimicrobial and tuberculostatic activities. The structures of the products <b style="mso-bidi-font-weight:normal">2-6</b> have been elucidated by elemental analyses and spectral data.</span>