Synthesis characterization and antibacterial, antifungal activity of n-(benzyl carbamoyl or carbamothioyl)-2-hydroxy substituted benzamide and 2-benzyl amino-substituted benzoxazines

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Date: Annual 2013
Publisher: Hindawi Limited
Document Type: Report
Length: 15,018 words
Lexile Measure: 1400L

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Abstract :

New N-(benzyl carbamothioyl)-2-hydroxy substituted benzamides 13, 20, and 21 were synthesized using sodium bicarbonate and benzyl amine with 2-thioxo-substituted-1,3-benzoxazines 6, 10a, b, 11c, and 12a-n. The 2-thioxo-substituted-1,3-oxazines 6,10ab, 11d 12a-n, and 26 were converted to the corresponding 2-methylthio-substituted-1,3-oxazines 14a-l and 24 which were then converted to 2-benzyl amino-substituted-benzoxazines 15a-i by refluxing with benzylamine. Products 15a, b, e, f, and g were also synthesized by boiling the corresponding N-(benzyl carbamothioyl)-2-hydroxy substituted benzamides 13a, b, f, l, and m in acetic acid. 2-Oxo-substituted-1,3-benzoxazines 22 and 25 were prepared by treating the corresponding 2-methylthio-substituted- 1,3oxazines 14 and 24 with dilute HCl. The N-(benzyl carbamoyl)-2-hydroxy substituted benzamide 23 was synthesized from the reaction of 2-oxo-substituted-1,3-benzoxazine 22 with benzylamine. The new products were characterized using IR, [sup1]H, and [sup.13]C NMR in addition to microanalysis. Selected compounds were tested in vitro for antibacterial and antifungi activity and the most active compounds were found to be the 4-(substituted-benzylamino)-2-hydroxy benzoic acids 9a and d (M. chlorophenolicum, MIC 50 and 25 [micro]gm [L.sup.-1], resp.), N1, N3-bis (benzyl carbamothioyl)-4,6-dihydroxy-substituted phthalamides 20a and 20C (B. subtilis MIC 12.5, 50 [micro]gm [L.sup.-1], resp.) and 21 (M. chlorophenolicum, MIC 50 [micro]gm [L.sup.-1]).

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Gale Document Number: GALE|A374527558