3-(1H-imidazol-1-ylmethyl)-1H-indole | 19714-15-9

• 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-(1H-imidazol-1-ylmethyl)-1H-indole
• 英文别名: 1H-Indole, 3-(1H-imidazol-1-ylmethyl)-；3-(imidazol-1-ylmethyl)-1H-indole
• CAS: 19714-15-9
• 化学式: C₁₂H₁₁N₃
• mdl: MFCD00449959
• 分子量: 197.239
• InChiKey: FRADTKAUXQUOIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  452.8±20.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(1H-imidazol-1-ylmethyl)-1H-indole 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-(1H-imidazol-1-ylmethyl)-1H-indole-1-propanoic 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
• 作为产物：
  描述：

  N-(苯基磺酰基)-3-甲基吲哚 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 水 、 xylene 为溶剂， 反应 24.0h， 生成 3-(1H-imidazol-1-ylmethyl)-1H-indole
  参考文献：
  名称：

  Nagarathnam, Dhanapalan, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 953 - 958

  摘要：

  DOI：

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。
• The Reaction of Carbonyldiimidazole with Alcohols to Form Carbamates and<i>N-</i>Alkylimidazoles
  作者：Jonathan L. Vennerstrom、Yuanqing Tang、Yuxiang Dong

  DOI：10.1055/s-2004-831215

  日期：——

  The reactions of non-benzylic primary and secondary aliphatic alcohols with carbonyldiimidazole (CDI) afford the corresponding carbamates but not N-alkylimidazoles. For benzylic primary alcohols, formation of N-alkylimidazoles proceeds reasonably at 170 °C in several different solvents and occurs by way of the initially formed carbamate. However, under these rather forcing conditions, or even at lower

  非苄基伯醇和仲脂肪醇与羰基二咪唑 (CDI) 的反应得到相应的氨基甲酸酯，但没有得到 N-烷基咪唑。对于苄基伯醇，N-烷基咪唑的形成合理地在 170 °C 下在几种不同的溶剂中进行，并通过最初形成的氨基甲酸酯发生。然而，在这些相当强制的条件下，甚至在较低的反应温度下，消除对于具有 β-氢原子的苄基仲醇来说是一个重要的副反应。除了一个例外，六种 N,N-二取代的 β-氨基醇与 CDI 形成 N-烷基咪唑的反应在相对温和的条件下进行，并且可能通过氮丙啶中间体发生。
• Synthesis andIn Vitro Evaluation of 3-(1-Azolylmethyl)-1H-indoles and 3-(1-Azolyl-1-phenylmethyl)-1H-indoles as Inhibitors of P450 arom
  作者：Marc Le Borgne、Pascal Marchand、Muriel Duflos、Bénédicte Delevoye-Seiller、Sylvie Piessard-Robert、Guillaume Le Baut、Rolf W. Hartmann、M. Palzer

  DOI：10.1002/ardp.19973300506

  日期：——

  In the challenge to develop potent inhibitors of aromatase for reducing the levels of estrogens, we found that azolyl‐substituted indoles inhibit aromatase activity. 3‐(1‐Azolylmethyl)‐1H‐indoles 9–15 and 3‐(1‐azolyl‐1‐phenylmethyl)‐1H‐indoles 22–25 were prepared, and tested on their ability to inhibit P450 arom. Analysis of the inhibitory effect exerted by several derivatives (11, 12, 22, and 23)

  在开发有效的芳香酶抑制剂以降低雌激素水平的挑战中，我们发现唑基取代的吲哚会抑制芳香酶活性。制备了3-(1-Azolylmethyl)-1H-indoles 9-15和3-(1-azolyl-1-phenylmethyl)-1H-indoles 22-25，并测试了它们抑制P450 arom的能力。抑制分析几种衍生物（11、12、22 和 23）对微粒体芳香酶体外活性的影响表明，含有咪唑部分的唑基取代吲哚是比三唑衍生物更有效的抑制剂。在第一个系列中，已发现 N-苄基部分的引入增强了这些 3-(1-唑基甲基)-1H-吲哚衍生物的抑制作用。相应的 4-氟衍生物 12 显示出最高的抑制活性 (IC50 = 0. 0718 μM) 的所有研究化合物；因此，12 的效力是氨鲁米特 (AG) 的 258 倍。化合物 22 和 24 中苯环对位的氯基团的存在仅在三唑 - 1 - 基亚系列中发挥积极作用：化合物
• Imidazole derivatives and antiepileptics comprising said imidazole
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US05112841A1

  公开（公告）日：1992-05-12

  Described herein are imidazole derivatives having a specific structure and satisfactory as antiepileptics from the standpoint of the strength of action, prolonged action and side effects as well as their preparation processes.

  本文描述了具有特定结构的咪唑衍生物，从作用强度、持续时间和副作用等方面来看，它们作为抗癫痫药物具有满意的效果，同时还涉及它们的制备过程。
• 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。