3-(imidazol-1-ylmethyl)-5-methoxyindole | 72818-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(imidazol-1-ylmethyl)-5-methoxyindole
• 英文别名: 3-(1-imidazolylmethyl)-5-methoxyindole；3-(imidazol-1-ylmethyl)-5-methoxy-1H-indole
• CAS: 72818-38-3
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: GKIXADSCPKQIOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(imidazol-1-ylmethyl)-5-methoxyindole 在 氢氧化钾 、 苄基三甲基氢氧化铵 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 4.5h， 生成 3-(3-Imidazol-1-ylmethyl-5-methoxy-indol-1-yl)-propionic acid
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 2. 3-(1H-Imidazol-1-ylmethyl)-2-methyl-1H-indole-1-propanoic acid and analogs.

  摘要：

  The preparation of a series of 3-(1H-imidazol-1-ylmethyl)-1H-indole-1-alkanoic acids is described. Several compounds were found to be more potent thromboxane synthetase inhibitors than the corresponding analogues lacking an acidic substituent. In the cases examined, compounds had no significant activity against PGI2 synthetase or cyclooxygenase, and introduction of the carboxylic acid substituent led to a reduction in activity against adrenal steroid 11 beta-hydroxylase. Compound 21 strongly inhibited thromboxane formation after iv administration to anesthetized rabbits and oral administration to conscious dogs. The compound had a long duration of action, and marked inhibition of thromboxane production was observed 15 h after oral administration of 1 mg/kg to conscious dogs.

  DOI：

  10.1021/jm00153a007

文献信息

• Inhibition of thromboxane synthetase by 3-(1-Imidazolylalkyl) indoles
  申请人：Pfizer Inc.

  公开号：US04273782A1

  公开（公告）日：1981-06-16

  Novel 3-(1-Imidazolylalkyl)indoles and the pharmaceutically acceptable acid addition salts thereof are disclosed. The novel compounds are useful in selectively inhibiting the action of the thromboxane synthetase enzyme without significantly inhibiting the action of the prostacycline synthetase or cyclooxygenase enzymes and are thus of value as therapeutic agents for the treatment of ischaemic heart disease, stroke, transient ischaemic attack, thrombosis, migraine and the vascular complications of diabetes.

  本文披露了新型3-(1-咪唑基烷基)吲哚化合物及其药用酸盐。这些新型化合物可用于选择性抑制血栓素合酶酶的作用，而不显著抑制前列环素合酶或环氧合酶的作用，因此对于治疗缺血性心脏病、中风、短暂性缺血性发作、血栓形成、偏头痛和糖尿病的血管并发症具有治疗价值。
• Inhibition of thromboxane synthetase with 3-(imidazol-1-ylalkyl)indoles
  申请人：Pfizer Inc.

  公开号：US04217357A1

  公开（公告）日：1980-08-12

  A series of unsubstituted and substituted 3-(imidazol-1-ylalkyl)indole compounds has been prepared by reacting the appropriately substituted 3-methylindole starting material with imidazole per se, followed by further reaction with a proper acylating or alkylating agent of choice, if so desired. The resulting indole derivatives are useful in therapy for the treatment at ischaemic heart disease, migraine, transient ischaemic attack and stroke. Typical members include such preferred compounds as 3-(imidazol-1-ylmethyl)-1-methylindole and 3-(imidazol-1-ylmethyl)-2-isopropylindole, respectively.

  一系列未取代和取代的3-(咪唑-1-基烷基)吲哚化合物是通过将适当取代的3-甲基吲哚起始物质与咪唑本身反应，然后再与所选择的适当酰化或烷基化试剂进一步反应，如果需要的话，制备而成。所得的吲哚衍生物在治疗缺血性心脏病、偏头痛、短暂性缺血性发作和中风方面具有用途。典型的成员包括3-(咪唑-1-基甲基)-1-甲基吲哚和3-(咪唑-1-基甲基)-2-异丙基吲哚等优选化合物。
• 3-(Imidazol-1-ylalkyl)indoles as selective inhibitors of thromboxane synthetase,pharmaceutical compositions thereof, and methods for preparing them
  申请人：Pfizer Limited

  公开号：EP0003901A2

  公开（公告）日：1979-09-05

  Substituted 3-fimidazol-1-ylmethyl)indoles of the formula: wherein R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, lower cycloalkyl, adamantyl, or a phenyl or benzyl group in which the benzene ring is optionally mono-substituted with halogen, hydroxy, lower alkyl, lower alkoxy or trifluoromethyl; R3 is hydrogen, lower alkyl, allyl, 3-methyl-allyl, lower cycloalkyl-methyl, lower cydoalkyl-ethyl, lower alkoxylower alkyl, di(lower alkyl)amino-lower alkyl, lower alkanoyl, lower cycloalkyl-carbonyl, or a benzyl or benzoyl group in which the benzene ring is optionally substituted as in R2; and R4 is hydrogen, lower alkyl, lower alkoxy, halogen, hydroxy, trifluoromethyl, di(lower alkyl)amino, or a benzyloxy group in which the benzene ring is optionally substituted as in R2; are described which are selective inhibitors of the action of the thromboxane synthetase enzyme, but which do not significantly affect the actions of the prostacyclin synthetase or cyclo-oxygenase enzymes, and which are therefore useful in the treatment of ischaemic heart disease, stroke, transient ischaemic attack and migraine. All the compounds, except that In which R1, R2, R3 and R4 are each hydrogen, are novel. Methods for their preparation are also described.

  式中的被取代的 3-咪唑-1-基甲基)吲哚： 其中 R1 是氢或低级烷基； R2 是氢、低级烷基、低级环烷基、金刚烷基、或苯基或苄基，其中苯环可选地被卤素、羟基、低级烷基、低级烷氧基或三氟甲基单取代； R3 是氢、低级烷基、烯丙基、3-甲基-烯丙基、低级环烷基-甲基、低级环烷基-乙基、低级烷氧基低级烷基、二（低级烷基）氨基低级烷基、低级烷酰基、低级环烷基-羰基，或其中苯环被 R2 中任选取代的苄基或苯甲酰基； 和 R4 是氢、低级烷基、低级烷氧基、卤素、羟基、三氟甲基、二（低级烷基）氨基或苄氧基，其中苯环如 R2 中那样被任选取代；所述化合物是血栓素合成酶作用的选择性抑制剂，但对前列环素合成酶或环氧化酶的作用无明显影响，因此可用于治疗缺血性心脏病、中风、短暂性脑缺血发作和偏头痛。除 R1、R2、R3 和 R4 均为氢的化合物外，所有化合物均为新型化合物。此外，还介绍了制备这些化合物的方法。
• CROSS, P. E.;DICKINSON, R. P.;PARRY, M. J.;RANDALL, M. J., J. MED. CHEM., 1986, 29, N 3, 342-346
  作者：CROSS, P. E.、DICKINSON, R. P.、PARRY, M. J.、RANDALL, M. J.

  DOI：——

  日期：——
• US4217357A
  申请人：——

  公开号：US4217357A

  公开（公告）日：1980-08-12