DESIGN, SYNTHESIS, MOLECULAR DOCKING AND EVALUATION OF ANTIMICROBIAL ACTIVITY OF 4- AMINO-N- [(4-OXO-2-(PHENYLAMINO)-4H-CHROMEN-3-YL) METHY-LENE]BENZENESULFONAMIDE AND THEIR DERIVATIVESAbstract
2-Anilino-3-formylchromones are obtained in high yield by rearrangement of differently substituted C-(4-oxo-4H-benzopyran-3-yl)-N-phenylnitrones. These compounds undergo various facile nucleophilic substitution reactions leading to the synthesis of various pharmacologically active chromone based novel heterocyclic systems like sulphonamides. The C-2 and C-3 are the main positions in the chromone moiety for the attack of nucleophiles and electrophiles, respectively. The chromone system behaves as Micheal acceptor. Generally, the nucleophilic attack at C-2 is accompanied by ring transformation. Protonation and alkylation occur on the oxygen of chromone moiety. In the present study, the substituted 3-Formylchromones were synthesized by Vilsmeyer haack Reaction. These substituted 3-Formylchromones were then reacted with phenyl hydroxyl amine in dry benzene to obtain substituted 2-Anilino-3-formylchromones which were further reacted with various substituted sulphonamides in dry alcohol to furnish final derivatives, i.e. chromone based sulphonamide derivatives (8a-h). Chemical structures of these synthesized derivatives were characterized by I.R Spectroscopy, 1H-NMR, 13C-NMR, and Mass spectroscopy analysis. Further, these obtained chromone based sulfonamide derivatives (8a-h) were evaluated in-vitro for their antibacterial and antifungal activities. Staphylococcus aureus, Bacillus subtilis, Pseudomonas aerogenosa, and E. coli bacterial strains were used for the purpose and similarly, the fungal strains used were Aspergillus niger and Candida albicans. All the tested compounds (8a-h) exhibited potent antimicrobial activities.
A. Chopra, L. Singh *, V. K. Kapoor, R. Dhingra and N. Dhingra
C. G. C. College of Engineering, Landran, Mohali, Punjab, India.
18 March 2019
23 May 2019
26 May 2019
01 June 2019