KMCH College of Pharmacy, Coimbatore, Tamilnadu, India.
Eur Rev Med Pharmacol Sci. 2013 Jan;17(1):95-104.
A series of ten novel derivatives of 3-substituted-2-thioxoquinazolin-4(3H)-ones have been synthesized from anthranilic acid via Mannich reaction with various secondary amines in presence of formaldehyde in ice cold condition.
The structure of these compounds have been elucidated by spectral (FTIR, 1H-NMR and mass) analysis. The titled compounds were evaluated for antimicrobial and anticonvulsant activities. Antimicrobial activities were determined by cup plate method and MIC values using the micro dilution broth method against two Gram positive bacteria Staphylococcus aureus and Streptococcus aureus, two Gram negative bacteria Escherichia coli and Proteus vulgaris and against two fungi Candida albicans and Aspergillus niger. Amikacin and fluconazole were used as standard antibacterial and antifungal agents in the concentration of 10 µg/disc 20 µg/disc respectively.
Amongst the compounds tested, compound 2-(2,3-dimethylphenyl) (3-(4-ethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydroquinazolin-1-2H)-1ylmethyl amino)benzoic acid (PTQ-03) and 2-((2,3-dimethylphenyl)((3-(4-ethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)amino)benzoic acid (ETQ-03) showed broad spectrum of activity against all the tested Gram positive bacteria, Gram negative bacteria and the fungi. Anti-convulsant activity of the compounds was evaluated by maximal electro shock (MES) convulsion method. The compounds sodium 2-(2-((2,6-Dichlorophenyl)(3-(4-oxo-2-thioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)amino) phenyl acetate (PTQ-04) and N-(4-Hydroxyphenyl)-N-((3-naphthalen-2-yl)-4-oxo-2-thioxo-3,4-dihydorquinazolin-1(2H)-ylmethyl)acetamide (NTQ-01) showed potent anticonvulsant activity.
通过曼尼希反应，在冰冷条件下用甲醛与各种仲胺与邻氨基苯甲酸合成了一系列十个新型 3-取代-2-硫代喹唑啉-4（3H）-酮衍生物。
通过光谱（FTIR、1H-NMR 和质谱）分析阐明了这些化合物的结构。对这些化合物进行了抗菌和抗惊厥活性评价。采用杯碟法和微量稀释肉汤法测定了对两种革兰氏阳性菌金黄色葡萄球菌和链球菌、两种革兰氏阴性菌大肠杆菌和普通变形杆菌以及两种真菌白色念珠菌和黑曲霉的最小抑菌浓度（MIC）值。阿米卡星和氟康唑分别作为标准抗菌和抗真菌药物，浓度为 10 µg/disc 和 20 µg/disc。
在所测试的化合物中，化合物 2-（2,3-二甲基苯基）（3-（4-乙氧基苯基）-4-氧代-2-硫代-3,4-二氢喹唑啉-1-2H）-1-基甲基氨基）苯甲酸（PTQ-03）和 2-（（2,3-二甲基苯基）（（3-（4-乙氧基苯基）-4-氧代-2-硫代-3,4-二氢喹唑啉-1-2H）-1-基甲基氨基）苯甲酸（ETQ-03）对所有测试的革兰氏阳性菌、革兰氏阴性菌和真菌均表现出广谱活性。通过最大电休克（MES）惊厥法评价了化合物的抗惊厥活性。化合物钠 2-（2-（（2,6-二氯苯基）（3-（4-氧代-2-硫代-3,4-二氢喹唑啉-1-2H）-1-基甲基氨基）苯基）乙酸盐（PTQ-04）和 N-（4-羟基苯基）-N-（（3-萘-2-基）-4-氧代-2-硫代-3,4-二氢喹唑啉-1-2H）-1-基甲基）乙酰胺（NTQ-01）表现出较强的抗惊厥活性。
