Synthesis, Characterization of New Phenylene Bis Tetrazole and Bis Benzoxazepinedione Derivatives from some Bis Imines with its Biological Activity Assessment.

Shakhawan Beebany
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Abstract

Some new phenylene bis tetrazole (T1-3) and bis benzoxazepinedione (B1-3) derivatives have been successfully synthesized through cyclization reaction for some bisimines (S1-3). The bisimines were transferred to heterocyclic compounds by adding sodium azide and phthalic anhydride to form bistetrazoles and bisbenzoxazepinediones respectively. The structures of the prepared compounds have been identified using infrared spectroscopy technique (FT-IR), the proton nuclear magnetic resonance (1HNMR) and the carbon nuclear magnetic resonance 13CNMR. Antibacterial effect of the novel compounds has been evaluated against Staphylococcus aureus (gram-positive bacteria) and Escherichia coli (gram-negative bacteria). The results indicated that bistetrazole T1 and bisbenzoxazepinedione B1 showed the highest inhibition zone against the growth of the applied bacteria. This may relate to presence of dimethyl amino group (CH3)2N increasing the potential of bacterial cell attack by the tested compound as this substituent can behave as donating group. This leads to less resistivity from bacteria to the tested compound resulting in an increase in the inhibition zone. Thus, tetrazole and oxazepine derivatives bearing dimethyl amino group should be considered as antibacterial agents for drug industry application field.
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双亚胺衍生物苯基双四唑及双苯并恶氮平二酮的合成、表征及生物活性评价
通过二亚胺(S1-3)的环化反应,成功合成了新的苯基双四唑(T1-3)和双苯并恶氮平二酮(B1-3)衍生物。通过添加叠氮化钠和邻苯二酸酐,将二亚胺转化为杂环化合物,分别生成双四唑和双苯并恶氮平二酮。利用红外光谱技术(FT-IR)、质子核磁共振(1HNMR)和碳核磁共振(13CNMR)对所制备化合物的结构进行了鉴定。新化合物对金黄色葡萄球菌(革兰氏阳性菌)和大肠杆菌(革兰氏阴性菌)的抑菌效果进行了评价。结果表明,双四唑T1和双苯并恶氮平二酮B1对施菌的抑制作用最强。这可能与二甲基氨基(CH3)2N的存在增加了被试化合物攻击细菌细胞的潜力有关,因为这个取代基可以作为给体基。这导致细菌对被测化合物的电阻率降低,从而导致抑制区增加。因此,含二甲基氨基的四氮唑和恶氮平衍生物应考虑作为药物工业应用领域的抗菌剂。
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