<abstract xmlns="http://www.w3.org/1999/xhtml"><p>In the present work, interaction of the strategic starting material, methyl 2-isothiocyanatobenzoate (1), with sulfa drugs resulted in the formation of methyl 2-[3-(4-(N-substituted sulfamoyl)phenyl)thioureido] benzoates 2-5, which upon reaction with hydrazine hydrate afforded N-amino derivatives 6-9. Triazoloquinazoline derivatives 10-18 were obtained via reaction of compounds 6-8 with aromatic aldehydes. Also, the reaction of compound 8 with formic acid gave the corresponding triazoloquinazoline derivative 19. Triazinoquinazoline derivatives 22, 23 were obtained via reaction of N-amino derivatives 6 or 8 with ethyl chloroacetate. Interaction of 6 with diethyloxalate yielded triazoloquinazoline 26. The synthesized compounds were screened for their in vitro antimicrobial activities and some of them exhibited promising antibacterial activity compared to ampicillin as positive control. Compounds that revealed significant activity are able to satisfy effectively the proposed pharmacophore geometry.</p></abstract>

In the present work, interaction of the strategic starting material, methyl 2-isothiocyanatobenzoate (1), with sulfa drugs resulted in the formation of methyl 2-[3-(4-(N-substituted sulfamoyl)phenyl)thioureido] benzoates 2-5, which upon reaction with hydrazine hydrate afforded N-amino derivatives 6-9. Triazoloquinazoline derivatives 10-18 were obtained via reaction of compounds 6-8 with aromatic aldehydes. Also, the reaction of compound 8 with formic acid gave the corresponding triazoloquinazoline derivative 19. Triazinoquinazoline derivatives 22, 23 were obtained via reaction of N-amino derivatives 6 or 8 with ethyl chloroacetate. Interaction of 6 with diethyloxalate yielded triazoloquinazoline 26. The synthesized compounds were screened for their in vitro antimicrobial activities and some of them exhibited promising antibacterial activity compared to ampicillin as positive control. Compounds that revealed significant activity are able to satisfy effectively the proposed pharmacophore geometry.

Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety

Medicinal, Aromatic and Poisonous Plants Research Center (MAPPRC) College of Pharmacy, King Saud University Riyadh, Riyadh 11451 Saudi Arabia

Department of Drug Radiation Research National Center for Radiation Research and Technology, Atomic Energy Authority Nasr City, Cairo, Egypt

Department of Chemistry, Faculty of Science (Girls), Al-Azhar University Cairo, Egypt

Kayyali Chair, Pharmaceutical Technology Center (PTC), College of Pharmacy King Saud University, Riyadh 11451, Saudi Arabia

Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy Assiut University, Assiut 71527, Egypt

Department of Organic Chemistry Faculty of Pharmacy, October 6 University Cairo, Egypt

Acta Pharmaceutica

In the present work, interaction of the strategic starting material, methyl 2-isothiocyanatobenzoate (1), with sulfa drugs resulted in the formation of methyl...

Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety

Publié en ligne: 12 mars 2013

Pages: 1 - 18

DOI: https://doi.org/10.2478/acph-2013-0006

Mots clés
quinazolines, fused quinazolines, sulfonamide, antimicrobial, pharmacophore

This content is open access.

Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety

Publié en ligne: 12 mars 2013

Pages: 1 - 18

DOI: https://doi.org/10.2478/acph-2013-0006

Mots clésquinazolines, fused quinazolines, sulfonamide, antimicrobial, pharmacophore

This content is open access.

Mots clés
quinazolines, fused quinazolines, sulfonamide, antimicrobial, pharmacophore