US EPA

7491468 

Journal Article 

New sulfonamide and carbamate derivatives of 4-(Oxiran-2-Ylmethoxy)-9hcarbazole: Synthesis, characterization, antimicrobial and antioxidant activities 

Reddy, SL; Naresh, K; Raju, CN 

2013 

5 

1 

221-231 

English 

A series of new N-substituted sulfonamides, 9-(substituted phenylsulfonyl)-4-(oxiran-2-ylmethoxy)-9H-carbazole 6(a-d) and carbamates, substituted phenyl/aliphatic-4-(oxiran-2-ylmethoxy)-9H-carbazole-9-carboxylate8(a-f) were synthesized in high yields through simple straight forward reaction of 4-(oxiran-2-ylmethoxy)-9H-carbazole (3) with various substituted sulfonyl chlorides and chloroformates in the presence of sodium hydride as a base. The structures of the synthesized compounds were confirmed by IR, NMR (1H, 13C), mass and elemental analysis data. All the compounds were screenedin vitroantibacterial (Staphylococcus aureus, Bacillus subtilis and Escherichia coli), antifungal (Fusariumoxysporum, Candida albicans and Aspergillusniger) activities and antioxidant activities using DPPH and NO methods. All the compounds exhibited moderate to potent antimicrobial activities and good antioxidant activities. 

4-(Oxiran-2-ylmethoxy)-9H-carbazole; Antimicrobial activity; Antioxidant activity; Carbamates; Sulfonamides; 1,1 diphenyl 2 picrylhydrazyl; 2,2,2 trichloroethyl 4 (oxiran 2 ylmethoxy) 9h carbazole 9 carboxylate; 4 (oxiran 2 ylmethoxy) 9 (trifluoromethylsulfonyl) 9h carbazole; 4 (oxiran 2 ylmethoxy) 9h carbazole; 4 chlorophenyl 4 (oxiran 2 ylmethoxy) 9h carbazole 9 carboxylate; 4 nitrobenzyl 4 (oxiran 2 ylmethoxy) 9h carbazole 9 carboxylate; 4 nitrophenyl 4 (oxiran 2 ylmethoxy) 9h carbazole 9 carboxylate; 9 (4 bromophenylsulfonyl) 4 (oxiran 2 ylmethoxy) 9h carbazole; 9 (4 chloro 3 fluorophenylsulfonyl) 4 (oxiran 2 ylmethoxy) 9h carbazole; 9 (4 chloro 3 nitrophenylsulfonyl) 4 (oxiran 2 ylmethoxy) 9h carbazole; antifungal agent; antiinfective agent; antioxidant; butylcresol; carbamic acid derivative; carboxyl group; ciprofloxacin; ethyl 4 (oxiran 2 ylmethoxy) 9h carbazole 9 carboxylate; fluconazole; isobutyl 4 (oxiran 2 ylmethoxy) 9h carbazole 9 carboxylate; nitric oxide; sulfonamide; unclassified drug; antibacterial activity; antifungal activity; antimicrobial activity; antioxidant activity; article; Aspergillus niger; Bacillus subtilis; Candida albicans; carbon nuclear magnetic resonance; chemical reaction kinetics; controlled study; drug determination; drug effect; drug screening; drug structure; drug synthesis; Escherichia coli; Fusarium oxysporum; in vitro study; infrared spectroscopy; nonhuman; proton nuclear magnetic resonance; Staphylococcus aureus; structure analysis