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Coumarin derivatives Synthesis and antimicrobial activity of certain sulphonamide, sulphonylhydrazine and sulphonyl azide derivatives of 4-methyl-7-hydroxycoumarin

Badran, M.M.; Ismail, M.A. Hamid; Ismail, M.M.; Abdel Hakeem, M.

Egyptian Journal of Pharmaceutical Sciences 33(5-6): 1081-1098

1993


Accession: 030739223

THE SYNTHESIS of novel coumarin-6-sulphonamide, sulphonylhdrazine and sulphonyl azide derivatives is described. Treatment of 7-hydroxy-4-methylcoumarin-6-sulphonyl chloride (I) with 5 moles of hydrazine hydrate afforded the sulphonylhydrazine (II), whereas using 1.5 moles of the reagent produced the N-1, N-2-bis (7-hydroxy-4-methyl coumarin-6-sulphonyl) hydrazine (III). The later compound was also obtained by condensation of (II) with (I). Reaction of (II) with acyl chlorides, nitrous acid and 1,3-dicarbonyl compounds, independently, gave N-2-acyl-N-1-coumarinsulphonylhydrazines (IV, a-c), coumarinsulphonyl azide (v) and coumarinsulphonylhydrazones (VI, a-b). The azide (V) can be converted to benzopyrano (6,7-d) (1,2,3) oxathiazole (VII) upon thermolysis in xylene. Hydrolysis of (VII) gave 6-amino-7-hydroxy-4-methylcoumarin (VIII). Heating the hydrazide (II) or its hydrazone derivatives (VI, a-b) resulted in the formation of bis (7-hydroxy-4-methyl coumarin-6-yl) disulphide (IX). Moreover, condensation of the sulphonyl chloride (I) with certain heterocyclic amines, produced the respective coumarin-6-sulphonamides (x, a-b). However, using weak nucleophilic amines, under the same conditions, the dimer (XI) was produced. Preliminary antimicrobial screening and MIC determinations revealed that some of the new compounds possess potent antibacterial and antifungal activity.

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