ethyl 4-[2-(1-imidazolyl)ethoxy]-phenoxyacetate | 75912-67-3

• 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: ethyl 4-[2-(1-imidazolyl)ethoxy]-phenoxyacetate
• 英文别名: Ethyl 4-[2-(1-imidazolyl)ethoxy]phenoxyacetate；ethyl 2-[4-(2-imidazol-1-ylethoxy)phenoxy]acetate
• CAS: 75912-67-3
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: JXHKIFQVMHUCTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-[2-(1-imidazolyl)ethoxy]-phenoxyacetate 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以42%的产率得到<4-<2-(1H-imidazol-1-yl)ethoxy>phenoxy>acetamide
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles

  摘要：

  1-(2-Phenoxyethyl)-1H-imidazole was found to be an inhibitor of thromboxane (TxA2) synthetase, but it also inhibited the adrenal cytochrome P-450 enzyme steroid 11 beta-hydroxylase. The preparation of a series of analogues is described, and activity against TxA2 synthetase, PGI2 synthetase, cyclooxygenase, and steroid 11 beta-hydroxylase is discussed. Potency against TxA2 synthetase was increased by introduction of a carboxyl group at a suitable distance from the imidazole ring. A distance of 8.1-8.8 A between N-1 of the imidazole and the carboxyl carbon was found to be optimal. Introduction of a carboxyl group also had the effect of reducing activity against steroid 11 beta-hydroxylase. The most potent and selective compound was found to be 4-[2-(1H-imidazol-1-yl) ethoxy]benzoic acid (14).

  DOI：

  10.1021/jm00148a009
• 作为产物：
  描述：

  2-(4-羟基苯氧基)乙酸乙酯 在 sodium hydride 作用下， 反应 8.83h， 生成 ethyl 4-[2-(1-imidazolyl)ethoxy]-phenoxyacetate
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles

  摘要：

  1-(2-Phenoxyethyl)-1H-imidazole was found to be an inhibitor of thromboxane (TxA2) synthetase, but it also inhibited the adrenal cytochrome P-450 enzyme steroid 11 beta-hydroxylase. The preparation of a series of analogues is described, and activity against TxA2 synthetase, PGI2 synthetase, cyclooxygenase, and steroid 11 beta-hydroxylase is discussed. Potency against TxA2 synthetase was increased by introduction of a carboxyl group at a suitable distance from the imidazole ring. A distance of 8.1-8.8 A between N-1 of the imidazole and the carboxyl carbon was found to be optimal. Introduction of a carboxyl group also had the effect of reducing activity against steroid 11 beta-hydroxylase. The most potent and selective compound was found to be 4-[2-(1H-imidazol-1-yl) ethoxy]benzoic acid (14).

  DOI：

  10.1021/jm00148a009

文献信息

• N-(phenoxyalkyl)imidazoles as selective inhibitors of the thromboxane
  申请人：Pfizer Inc.

  公开号：US04602016A1

  公开（公告）日：1986-07-22

  N-(mono or disubstituted phenoxyalkyl)imidazoles and the pharmaceutically acceptable acid addition salts thereof are able to selectively inhibit the action of the thromboxane synthetase enzyme without significantly inhibiting the action of the prostacycline synthetase or cyclooxygenase enzymes and are thus useful in the treatment of ischaemic heart disease, stroke, transient ischaemic attack, thrombosis, migraine, and the vascular complications of diabetes.

  N-(单取代或双取代苯氧烷基)咪唑及其药用可接受的酸盐能够选择性地抑制血栓素合成酶酶的作用，而不显著抑制前列环素合成酶或环氧化酶酶的作用，因此在缺血性心脏病、中风、短暂性缺血发作、血栓形成、偏头痛以及糖尿病的血管并发症治疗中是有用的。
• CROSS, P. E.;DICKINSON, R. P.;PARRY, M. J.;RANDALL, M. J., J. MED. CHEM., 1985, 28, N 10, 1427-1432
  作者：CROSS, P. E.、DICKINSON, R. P.、PARRY, M. J.、RANDALL, M. J.

  DOI：——

  日期：——
• US4602016A
  申请人：——

  公开号：US4602016A

  公开（公告）日：1986-07-22
• US4636500A
  申请人：——

  公开号：US4636500A

  公开（公告）日：1987-01-13
• Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles
  作者：Peter E. Cross、Roger P. Dickinson、M. John Parry、Michael J. Randall

  DOI：10.1021/jm00148a009

  日期：1985.10

  1-(2-Phenoxyethyl)-1H-imidazole was found to be an inhibitor of thromboxane (TxA2) synthetase, but it also inhibited the adrenal cytochrome P-450 enzyme steroid 11 beta-hydroxylase. The preparation of a series of analogues is described, and activity against TxA2 synthetase, PGI2 synthetase, cyclooxygenase, and steroid 11 beta-hydroxylase is discussed. Potency against TxA2 synthetase was increased by introduction of a carboxyl group at a suitable distance from the imidazole ring. A distance of 8.1-8.8 A between N-1 of the imidazole and the carboxyl carbon was found to be optimal. Introduction of a carboxyl group also had the effect of reducing activity against steroid 11 beta-hydroxylase. The most potent and selective compound was found to be 4-[2-(1H-imidazol-1-yl) ethoxy]benzoic acid (14).