ethyl 6-methyl-2-methoxy-3-([4-methoxyphenyl]-2-oxoethyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1187376-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-methyl-2-methoxy-3-([4-methoxyphenyl]-2-oxoethyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(4-hydroxyphenyl)-2-methoxy-3-[2-(4-methoxyphenyl)-2-oxoethyl]-6-methyl-2,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1187376-85-7
• 化学式: C₂₄H₂₈N₂O₆
• 分子量: 440.496
• InChiKey: SZDRIMLSGMYDSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethyl 6-methyl-2-methoxy-4-(4-hydroxyphenyl)-1,4-dihydropyrimidine-5-carboxylate 、 alpha-溴-4-甲氧基苯乙酮 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以60%的产率得到ethyl 6-methyl-2-methoxy-3-([4-methoxyphenyl]-2-oxoethyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacological investigation of 3-(substituted 1-phenylethanone)-4-(substituted phenyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylates

  摘要：

  Fifteen new ethyl 6-methyl-2-methoxy-3-(substituted 1-phenylethanone)4-(substituted phenyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylates (6a-o) have been synthesized in a two step reaction. In first step ethyl acetoacetate, s-methylisourea and appropriate benzaldehydes reacted in a single step reaction to obtain ethyl 6-methyl-2-methoxy-4-(substituted phenyl)-1, 4-dihydropyrimidine-5-carboxylates (4a-e). Second step involves synthesis of reaction between substituted phenacyl bromides and 1-4-dihydropyrimidine-5-carboxylates (6a-o). Their structures are confirmed by IR, (1)H NMR, mass and elemental analyses. The compounds were tested for anti hypertensive activity by non-invasive tail-cuff, and evaluated by carotid artery cannulation method for determining the diastolic blood pressure. Hypertension was induced by DOCA-salt. Anti-inflammatory activity was carried out by carrageenan induced rat-paw oedema method. Test compounds 6b, 6c, 6e, 6f, 6j, 6h, 6k, 6l, 6m, 6n and 6o exerted comparative antihypertensive activity at 10 mg/kg dose level compared to nifedipine. Compounds 6j, 6m and 6o showed excellent results on evaluation by direct method. Test compounds 6a-6h, 6l, 6m, 6n and 6o exerted moderate to comparative anti-inflammatory activity at the 100 mg/kg dose level compared to indomethacin. Their further investigation for analgesic activity and acute ulcerogenesis was carried out, compounds 6m, 6f, 6k, 6o showed excellent to good analgesic activity and low ulcerogenic activity. (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.ejmech.2009.02.021

文献信息

• Synthesis and pharmacological investigation of 3-(substituted 1-phenylethanone)-4-(substituted phenyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylates
  作者：R.V. Chikhale、R.P. Bhole、P.B. Khedekar、K.P. Bhusari

  DOI：10.1016/j.ejmech.2009.02.021

  日期：2009.9

  Fifteen new ethyl 6-methyl-2-methoxy-3-(substituted 1-phenylethanone)4-(substituted phenyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylates (6a-o) have been synthesized in a two step reaction. In first step ethyl acetoacetate, s-methylisourea and appropriate benzaldehydes reacted in a single step reaction to obtain ethyl 6-methyl-2-methoxy-4-(substituted phenyl)-1, 4-dihydropyrimidine-5-carboxylates (4a-e). Second step involves synthesis of reaction between substituted phenacyl bromides and 1-4-dihydropyrimidine-5-carboxylates (6a-o). Their structures are confirmed by IR, (1)H NMR, mass and elemental analyses. The compounds were tested for anti hypertensive activity by non-invasive tail-cuff, and evaluated by carotid artery cannulation method for determining the diastolic blood pressure. Hypertension was induced by DOCA-salt. Anti-inflammatory activity was carried out by carrageenan induced rat-paw oedema method. Test compounds 6b, 6c, 6e, 6f, 6j, 6h, 6k, 6l, 6m, 6n and 6o exerted comparative antihypertensive activity at 10 mg/kg dose level compared to nifedipine. Compounds 6j, 6m and 6o showed excellent results on evaluation by direct method. Test compounds 6a-6h, 6l, 6m, 6n and 6o exerted moderate to comparative anti-inflammatory activity at the 100 mg/kg dose level compared to indomethacin. Their further investigation for analgesic activity and acute ulcerogenesis was carried out, compounds 6m, 6f, 6k, 6o showed excellent to good analgesic activity and low ulcerogenic activity. (C) 2009 Elsevier Ltd. All rights reserved