9-(1H-imidazol-1-yl)-8-{[(4-methoxyphenyl)methoxy]methyl}nonanoic acid | 109786-89-2

• 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: 9-(1H-imidazol-1-yl)-8-{[(4-methoxyphenyl)methoxy]methyl}nonanoic acid
• 英文别名: 9-Imidazol-1-yl-8-(4-methoxy-benzyloxymethyl)-nonanoic acid；8-(imidazol-1-ylmethyl)-9-[(4-methoxyphenyl)methoxy]nonanoic acid
• CAS: 109786-89-2
• 化学式: C₂₁H₃₀N₂O₄
• 分子量: 374.48
• InChiKey: ZAZLBFUOKKZIBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(1H-imidazol-1-yl)-8-{[(4-methoxyphenyl)methoxy]methyl}nonanoic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 生成 9-Imidazol-1-yl-8-(4-methoxy-benzyloxymethyl)-nonanoic acid ethyl ester
  参考文献：
  名称：

  Thromboxane synthase inhibitors. Synthesis and pharmacological activity of (R)-, (S)-, and (.+-.)-2,2-dimethyl-6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoic acids

  摘要：

  A series of substituted omega-[2-(1H-imidazol-1-yl)ethoxy]alkanoic acid derivatives were synthesized and evaluated for their ability to inhibit thromboxane synthase both in vitro and in vivo. Compound 13 was identified as a potent and selective competitive inhibitor of human platelet thromboxane synthase having a Ki value of 9.6 X 10(-8) M. In collagen-treated human whole blood, 13 potentiated levels of 6-keto PGF1 alpha. Enantiospecific syntheses afforded the R and S enantiomers of 13, of which the S enantiomer 13b was the more potent. Compounds 13 and 13b were potent in vivo inhibitors of thromboxane synthase with good oral activity and duration of action.

  DOI：

  10.1021/jm00393a022
• 作为产物：
  描述：

  methyl 4-(1H-imidazol-1-yl)-3-<<(4-methoxyphenyl)methoxy>methyl>-2-butenoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 草酰氯 、 potassium tert-butylate 、 氢气 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， -60.0~25.0 ℃ 、101.33 kPa 条件下， 反应 30.75h， 生成 9-(1H-imidazol-1-yl)-8-{[(4-methoxyphenyl)methoxy]methyl}nonanoic acid
  参考文献：
  名称：

  Thromboxane synthase inhibitors. Synthesis and pharmacological activity of (R)-, (S)-, and (.+-.)-2,2-dimethyl-6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoic acids

  摘要：

  A series of substituted omega-[2-(1H-imidazol-1-yl)ethoxy]alkanoic acid derivatives were synthesized and evaluated for their ability to inhibit thromboxane synthase both in vitro and in vivo. Compound 13 was identified as a potent and selective competitive inhibitor of human platelet thromboxane synthase having a Ki value of 9.6 X 10(-8) M. In collagen-treated human whole blood, 13 potentiated levels of 6-keto PGF1 alpha. Enantiospecific syntheses afforded the R and S enantiomers of 13, of which the S enantiomer 13b was the more potent. Compounds 13 and 13b were potent in vivo inhibitors of thromboxane synthase with good oral activity and duration of action.

  DOI：

  10.1021/jm00393a022

文献信息

• MANLEY, PAUL W.;TUFFIN, DAVID P.;ALLANSON, NIGEL M.;BUCKLE, PHILIP E.;LAD+, J. MED. CHEM., 30,(1987) N 10, 1812-1818
  作者：MANLEY, PAUL W.、TUFFIN, DAVID P.、ALLANSON, NIGEL M.、BUCKLE, PHILIP E.、LAD+

  DOI：——

  日期：——
• Thromboxane synthase inhibitors. Synthesis and pharmacological activity of (R)-, (S)-, and (.+-.)-2,2-dimethyl-6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoic acids
  作者：Paul W. Manley、David P. Tuffin、Nigel M. Allanson、Philip E. Buckle、Nagin Lad、Steve M. F. Lai、David O. Lunt、Roderick A. Porter、Patricia J. Wade

  DOI：10.1021/jm00393a022

  日期：1987.10

  A series of substituted omega-[2-(1H-imidazol-1-yl)ethoxy]alkanoic acid derivatives were synthesized and evaluated for their ability to inhibit thromboxane synthase both in vitro and in vivo. Compound 13 was identified as a potent and selective competitive inhibitor of human platelet thromboxane synthase having a Ki value of 9.6 X 10(-8) M. In collagen-treated human whole blood, 13 potentiated levels of 6-keto PGF1 alpha. Enantiospecific syntheses afforded the R and S enantiomers of 13, of which the S enantiomer 13b was the more potent. Compounds 13 and 13b were potent in vivo inhibitors of thromboxane synthase with good oral activity and duration of action.