1-(1H-imidazol-1-yl)-3-<(4-methoxyphenyl)methoxy>-2-propanone | 99500-31-9

• 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: 1-(1H-imidazol-1-yl)-3-<(4-methoxyphenyl)methoxy>-2-propanone
• 英文别名: 1-(1H-imidazol-1-yl)-3-[(4-methoxyphenyl)methoxy]-2-propanone；1-imidazol-1-yl-3-[(4-methoxyphenyl)methoxy]propan-2-one
• CAS: 99500-31-9
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: DTDIVCNZHAECNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1H-imidazol-1-yl)-3-<(4-methoxyphenyl)methoxy>-2-propanone 在 lithium aluminium tetrahydride 、 草酰氯 、 potassium tert-butylate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 100.75h， 生成 (Z)-8-(imidazol-1-ylmethyl)-9-[(4-methoxyphenyl)methoxy]non-5-enoic 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
• 作为产物：
  描述：

  α-<<(4-methoxyphenyl)methoxy>methyl>-1-H-imidazole-1-ethanol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以92%的产率得到1-(1H-imidazol-1-yl)-3-<(4-methoxyphenyl)methoxy>-2-propanone
  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

• Substituted alkylidene imidazoles
  申请人：G.D. Searle & Co.

  公开号：EP0150892B1

  公开（公告）日：1991-04-24
• MANLEY, PAUL W.;PORTER, RODERICK A.;LAI, MUN F.
  作者：MANLEY, PAUL W.、PORTER, RODERICK A.、LAI, MUN F.

  DOI：——

  日期：——
• 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：——
• US4837333A
  申请人：——

  公开号：US4837333A

  公开（公告）日：1989-06-06
• 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.