Synthesis, characterization and antifungal activities of some benzenesulphonylamino acid derivatives.
Condensation of benzenesulphonyl chloride (1) with a series of amino acids afforded benzenesulphonylamino acids (2a-d). Esterification of the derivatives (2a-d) in methanol gave the corresponding benzensulphonylamino acid methylesters (3a-d), which condensed with o-aminophenol and o-phenylene diamine to give the benzoxazoles (4a-d) and benximidazoles (5a-d) respectively. Hydrazinolysis of the methyl esters (3a-d) afforded the hydrazide derivatives (6a-d). The 1,2-diazeridine derivatives (7a-d) can be prepared by the reaction of hydrazides (6a-d) with alpha-chloroacetylchloide. Schiff's bases (10a-d) were achieved by the condensation of p-chlorobenzaldehyde with the hydrazides (6a-d). Condensation of Schiff's bases (10a-d) with p-chlorophenyldiazonium chloride afforded the formazan derviatives (11a-d). The hydrazides (6a-d) were reacted with acetylethylacetate to give 3-methyl-2-pyrazoline-2-one derivatives (8a-d), which condensed with p-chlorobenzaldehyde to give 4-arylidino-3-methyl-2-pyrazoline-2-one derivatives (9a-d). All derivatives (2-11) were tested against: A. flavus, A. parasiticus, A. alutaceus and F. moniliforme. Some of the derivatives showed promising results against the tested fungi.
Abdel-Ghaffar
S A
SA
Department of Chemistry, Makerere University, Kampala, Uganda.
Mpango
G B
GB
Ismail
M A
MA
Nanyonga
S K
SK
D000596:Amino Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001557:Benzenesulfonates / Q000138:chemical synthesis* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D000596:Amino Acids; D000935:Antifungal Agents; D001557:Benzenesulfonates; D007202:Indicators and Reagents; D011720:Pyrazoles