Zeid Hassan Abood
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Synthesis and Preliminary Antibacterial Activities of New 2, 3-Disubstituted-1, 3-Oxazepane-4, 7-Diones of Benzothiazole Zeid Hassan Abood
Journal of Global Pharma Technology Volume 12 Issue 02 (2020) Feb. 2020
Publisher : Journal of Global Pharma Technology

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Abstract

2-aminobenzothiazole 1 was converted to analogues diazonium salt which reacted with alkaline solution of 2-hydroxybenzaldehyde to yield azo-benzothiazole derivative 2 bearing aldehyde group. The resulting aldehyde 2 was then condensed with some aromatic amines including (4-nitroaniline, 3-nitroaniline, 4-aminophenol, 4-methoxyaniline, 4-bromoaniline, 4-chloroaniline and 2, 4-dichloroaniline) using microwave irradiation technique in absolute ethanol to produce seven imine derivatives of benzothiazole 3a-g, respectively. Treatment of the resulting imines 3a-g with succinic anhydride using microwave irradiation in dry benzene afforded seven new 1, 3-oxazepane-4, 7-diones 4a-g bearing the benzothiazole moiety, respectively. Preliminary in vitro antibacterial activity of the target compounds were investigated using two types of bacteria, Staphylococcus aurous (Gram-positive) and Escherichia coli (Gram-negative). The results indicated that all oxazepane compounds exhibited better activity to gentamycin against Gram-positive bacteria. On the other hand, the oxazepane compounds (4a, 4e and 4g) showed greater activity against Gram-negative bacteria when compared with that of the control drug.Keywords: Benzothiazoles; Oxazepanes; Imines; Azo; Antibacterial activity.
Synthesis and Preliminary Antibacterial Effects of New 1, 3, 4-Oxadiazoles Zeid Hassan Abood
Journal of Global Pharma Technology Volume 12 Issue 02 (2020) Feb. 2020
Publisher : Journal of Global Pharma Technology

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Abstract

4-aminobenzoyl hydrazide [I] was reacted with carbon disulfide in the existence of potassium hydroxide in ethyl alcohol to give 5-(4-aminophenyl)-2-thiol-1,3,4-oxadiazole [II]. The initiator aldehyde [III] was prepared via coupling reaction of 2-hydroxybenzaldehyde with the corresponding diazonium salt of compound [II]. Aldehyde [III] was condensed with some anilines including (3-bromoaniline, 4-aminophenol, 3-aminophenol, 2-aminophenol, 4-methoxyaniline, 2, 4-dimethylaniline and 4-acetamidoaniline) utilizing microwave irradiation technique in ethyl alcohol to yield seven imines [IV] a-g. Treatment of imines [IV]a-g with phthalic anhydride in microwave oven gave seven 1,3-benzoxazepine-4,7-diones derivatives of 1,3,4-oxadiazole [V]a-g. The antibacterial activities for the desired compounds were investigated on bacteria, Staphylococcus aurous and Escherichia coli. The results showed that the synthesized 1, 3, 4-oxadiazoles (compounds [V]a, [V]b, [V]c, [V]d and [V]e expressed better activity to gentamycin athwart positive bacteria. On the other hand, the 1,3-oxazepine-4,7-diones [V]a, [V]b, [V]c, [V]d, [V]f and [V]g exhibited greater effect against negative bacteria in comparison with that of the control drug (Gentamycin).Keywords: 1, 3, 4-Oxadiazoles, Benzoxazepines, Imines, Cycloaddition, Antibacterial action.