Synthesis, characterization, antimicrobial and single crystal X-ray crystallographic studies of some new sulfonyl, 4-chloro phenoxy benzene and dibenzoazepine substituted benzamides

• Published in: European journal of medicinal chemistry 2006-11, Vol.41 (11), p.1262-1270
• Main Authors: Priya, B.S., Nanjunda Swamy, S., Tejesvi, M.V., Basappa, Sarala, G., Gaonkar, S.L., Naveen, S., Shashidhara Prasad, J., Rangappa, K.S.
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Azepines - chemical synthesis; Azepines - chemistry; Azepines - pharmacology; Benzamide; Benzamides - chemical synthesis; Benzamides - chemistry; Benzamides - pharmacology; Biological and medical sciences; Crystallography, X-Ray; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Magnetic Resonance Spectroscopy; Medical sciences; Microbial Sensitivity Tests; Mitosporic Fungi - drug effects; Molecular Structure; Monoclinic; Pharmacology. Drug treatments; Spectrophotometry, Infrared; Triclinic
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2006.05.011

A new class of benzamide derivatives 3a(I–VI) and 3b(I–VI), bearing different bioactive moieties were synthesized and evaluated for their efficacy as antimicrobials in vitro. Compounds 3bVI, 3aII, 3aV, 3bIII, 3aVI, 3bII showed significant antibacterial activity and 3bIII, 3bII, 3aIV, 3bV, 3bVI, 3aI exhibit significant antifungal activity. The title compounds are characterized by spectral and elemental analysis. Compounds 2-methoxy- N-[4-(thiazol-2-yl-sulfamoyl)-phenyl]-benzamide 3aII and 2-(2-(2-ethoxybenzoylamino) phenethyl)- N-(2-ethoxybenzoyl) benzenamine 3bV are characterized by the single crystal X-ray studies. Compound 3aII crystallizes in monoclinic space group P2 1 and 3bV in triclinic space group P-1 . Compounds 3aII and 3bV exhibit both inter and intra molecular hydrogen bonding. A new class of benzamide derivatives 3a(I–VI) and 3b(I–VI), bearing different bioactive moieties were synthesized and evaluated for their efficacy as antimicrobials in vitro. Compounds 3bVI, 3aII, 3aV, 3bIII, 3aVI, 3bII showed significant antibacterial activity and 3bIII, 3bII, 3aIV, 3bV, 3bVI, 3aI exhibit significant antifungal activity. The title compounds are characterized by spectral and elemental analysis. Compounds 2-methoxy- N-[4-(thiazol-2-yl-sulfamoyl)-phenyl]-benzamide 3aII and 2-(2-(2-ethoxybenzoylamino) phenethyl)- N-(2-ethoxybenzoyl) benzenamine 3bV are characterized by the single crystal X-ray studies. Compound 3aII crystallizes in monoclinic space group P2 1 and 3bV in triclinic space group P1. Compounds 3aII and 3bV exhibit both inter and intra molecular hydrogen bonding.