Some New Heterocyclic Sulphonates with potential antimicrobial activity

✍ Scribed by Dr. O. M. O. Habib; E. B. Moawad; D. S. Badawy; F. A. Mansour

• Book ID: 105353758
• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 341 KB
• Volume: 332
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19903320531

✦ Synopsis

Abstract

4‐(Phenylhydrazono‐4′‐benzenesulphonato)‐3‐methyl‐2‐pyrazolin‐5‐one (2) was prepared by treating 4‐(4′‐hydroxyphenylhydrazono)‐3‐methyl‐2‐pyrazolin‐5‐one (1) with benzenesulphonyl chloride. Heating 2 with acetic anhydride, chloroacetyl chloride and benzenesulphonyl chloride afforded the N‐acetyl (3), N‐chloroacetyl (4) and O‐benzenesulphonyl (5) derivatives, respectively. 2 reacted with benzenesulphonyl chloride under cooling conditions to give the N‐benzenesulphonyl derivative (6). 2 undergoes Mannich reaction to give the N‐Mannich base (7). Reaction of 2 with formaldehyde in methanol afforded the N‐hydroxymethyl derivative (8) which undergoes condensation with ethyl acetoacetate, ethyl cyanoacetate and malononitrile to give compounds 9, 10 and 11 respectively. The antimicrobial activity of these products against gram‐positive (+ve), gram‐negative (−ve) bacteria and fungi was screened. They showed potential bactericidal activity and some of them exhibited high fungicidal activity.