5-<2'-(cyanobiphenyl-4-yl)methyl>-4-mercapto-2-methyl-6-n-propyl pyrimidine | 169772-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-<2'-(cyanobiphenyl-4-yl)methyl>-4-mercapto-2-methyl-6-n-propyl pyrimidine
• 英文别名: 2-[4-[(2-methyl-6-propyl-4-sulfanylidene-1H-pyrimidin-5-yl)methyl]phenyl]benzonitrile
• CAS: 169772-85-4
• 化学式: C₂₂H₂₁N₃S
• 分子量: 359.495
• InChiKey: PGELPBNDLGOYAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-<2'-(cyanobiphenyl-4-yl)methyl>-4-mercapto-2-methyl-6-n-propyl pyrimidine 在 trimethyltin azide 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以49%的产率得到4-mercapto-2-methyl-6-n-propyl-5-<<2'-(1H-tetrazol-5-yl)-biphenyl-4-yl>methyl>pyrimidine
  参考文献：
  名称：

  Synthesis and angiotensin II receptor antagonist activity of C-linked pyrimidine derivatives

  摘要：

  The synthesis and pharmacological activity of nonpeptide angiotensin II (Ang II) receptor antagonists are presented. These 3-N-substituted pyrimidine-4(3H)-one and 4-O,N,S-substituted pyrimidine derivatives represent a series of C-linked biphenyl tetrazole Ang II antagonists. In vitro, they displayed a high affinity for rat adrenal Ang II receptors, several compounds causing more than 60% displacement of [I-125]Sar(1)-Ile(8)-Ang II from the rat adrenal Ang II receptor at 10(-7) M. In vivo, several compounds displayed a high oral antihypertensive activity in renal hypertensive rat with decreases in systolic arterial pressure (SAP) greater than 60 mmHg 10 mg/kg. 2-[2-Methyl-4-oxo-6-n-propyl-5-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidin-3-yl]ethanol hydrochloride (compound 17) was compared with Losartan in the renal artery-ligated rat model. It was shown that at 3 mg/kg po, 17 induced a maximal decrease in mean arterial pressure (MAP) of 60.8 mmHg, which was similar to that was observed with Losartan (maximal decrease of 60 mmHg at 3 mg/kg) with a long duration of action (greater than 16 h).

  DOI：

  10.1016/0223-5234(96)88246-8
• 作为产物：
  描述：

  2-氰基-4'-溴甲基联苯 在 盐酸 、 氢氧化钾 、 sodium methylate 、 N,N-二异丙基乙胺 、 lithium chloride 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 30.25h， 生成 5-<2'-(cyanobiphenyl-4-yl)methyl>-4-mercapto-2-methyl-6-n-propyl pyrimidine
  参考文献：
  名称：

  Synthesis and angiotensin II receptor antagonist activity of C-linked pyrimidine derivatives

  摘要：

  The synthesis and pharmacological activity of nonpeptide angiotensin II (Ang II) receptor antagonists are presented. These 3-N-substituted pyrimidine-4(3H)-one and 4-O,N,S-substituted pyrimidine derivatives represent a series of C-linked biphenyl tetrazole Ang II antagonists. In vitro, they displayed a high affinity for rat adrenal Ang II receptors, several compounds causing more than 60% displacement of [I-125]Sar(1)-Ile(8)-Ang II from the rat adrenal Ang II receptor at 10(-7) M. In vivo, several compounds displayed a high oral antihypertensive activity in renal hypertensive rat with decreases in systolic arterial pressure (SAP) greater than 60 mmHg 10 mg/kg. 2-[2-Methyl-4-oxo-6-n-propyl-5-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidin-3-yl]ethanol hydrochloride (compound 17) was compared with Losartan in the renal artery-ligated rat model. It was shown that at 3 mg/kg po, 17 induced a maximal decrease in mean arterial pressure (MAP) of 60.8 mmHg, which was similar to that was observed with Losartan (maximal decrease of 60 mmHg at 3 mg/kg) with a long duration of action (greater than 16 h).

  DOI：

  10.1016/0223-5234(96)88246-8

文献信息

• Synthesis and angiotensin II receptor antagonist activity of C-linked pyrimidine derivatives
  作者：E Nicolaï、G Curé、J Goyard、M Kirchner、JM Teulon、A Versigny、M Cazes、A Virone-Oddos、F Caussade、A Cloarec

  DOI：10.1016/0223-5234(96)88246-8

  日期：1995.1

  The synthesis and pharmacological activity of nonpeptide angiotensin II (Ang II) receptor antagonists are presented. These 3-N-substituted pyrimidine-4(3H)-one and 4-O,N,S-substituted pyrimidine derivatives represent a series of C-linked biphenyl tetrazole Ang II antagonists. In vitro, they displayed a high affinity for rat adrenal Ang II receptors, several compounds causing more than 60% displacement of [I-125]Sar(1)-Ile(8)-Ang II from the rat adrenal Ang II receptor at 10(-7) M. In vivo, several compounds displayed a high oral antihypertensive activity in renal hypertensive rat with decreases in systolic arterial pressure (SAP) greater than 60 mmHg 10 mg/kg. 2-[2-Methyl-4-oxo-6-n-propyl-5-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidin-3-yl]ethanol hydrochloride (compound 17) was compared with Losartan in the renal artery-ligated rat model. It was shown that at 3 mg/kg po, 17 induced a maximal decrease in mean arterial pressure (MAP) of 60.8 mmHg, which was similar to that was observed with Losartan (maximal decrease of 60 mmHg at 3 mg/kg) with a long duration of action (greater than 16 h).