Amir Mohammad, Javed Sadique Akhtar, Kumar Harish
Department of Pharmaceutical Chemistry, Hamdard University (Jamia Hamdard), New Delhi-10062, India.
Acta Pharm. 2008 Dec;58(4):467-77. doi: 10.2478/v10007-008-0028-x.
Twelve new 4-(1H-indol-3-yl)-6-phenyl-1,2,3,4-tetrahydropyrimidin-2-ones/thiones (7-18) have been synthesized by reacting 1-aryl-3-(1H-indol-3-yl)-2-propen-1-one with urea and thiourea in ethanolic potassium hydroxide. Their structures have been confirmed by IR, 1H NMR and mass spectral data. The compounds were tested for their anti-inflammatory activity. Test results revealed that compounds showed 49.5 to 70.7% anti-inflammatory activity where-as the standard drug ibuprofen showed 86.4% activity at the same oral dose. Four compounds, 4-(1H-indol-3-yl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-2-one (8), 4-(1H-indol-3-yl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-2-one (10), 4-(1H-indol-3-yl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-2-thione (14), 4-(1H-indol-3-yl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-2-thione (16), that showed significant anti-inflammatory activity were selected to study their ulcerogenic and lipid peroxidation activities. All tested compounds showed significant reduction in the ulcerogenic potential and lipid peroxidation compared to the standard drug ibuprofen.
通过在乙醇氢氧化钾中使1-芳基-3-(1H-吲哚-3-基)-2-丙烯-1-酮与尿素和硫脲反应，合成了12种新的4-(1H-吲哚-3-基)-6-苯基-1,2,3,4-四氢嘧啶-2-酮/硫酮(7-18)。它们的结构已通过红外光谱、1H核磁共振和质谱数据得到证实。对这些化合物进行了抗炎活性测试。测试结果表明，这些化合物表现出49.5%至70.7%的抗炎活性，而标准药物布洛芬在相同口服剂量下的活性为86.4%。选择了4种具有显著抗炎活性的化合物，即4-(1H-吲哚-3-基)-6-(4-氯苯基)-1,2,3,4-四氢嘧啶-2-酮(8)、4-(1H-吲哚-3-基)-6-(4-甲基苯基)-1,2,3,4-四氢嘧啶-2-酮(10)、4-(1H-吲哚-3-基)-6-(4-氯苯基)-1,2,3,4-四氢嘧啶-2-硫酮(14)、4-(1H-吲哚-3-基)-6-(4-甲基苯基)-1,2,3,4-四氢嘧啶-2-硫酮(16)，来研究它们的致溃疡和脂质过氧化活性。与标准药物布洛芬相比，所有测试化合物的致溃疡潜力和脂质过氧化均显著降低。
