5-(1-羟基-2-氨基乙基)-1H-吲哚-7-甲酰胺 | 101544-49-4

• 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
• 中文名称: 5-(1-羟基-2-氨基乙基)-1H-吲哚-7-甲酰胺
• 英文名称: 5-(2-amino-1-hydroxy-ethyl)-1H-indole-7-carboxamide
• 英文别名: AY 30191；5-(2-amino-1-hydroxyethyl)-1H-indole-7-carboxamide；5-(2-amino-1-hydroxyethyl)indole-7-carboxamide；5-(1-Hydroxy-2-aminoethyl)-1H-indole-7-carboxamide
• CAS: 101544-49-4
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: GHZFFYJKVKWIPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氯-2-甲氧基苯甲酸 、 5-(1-羟基-2-氨基乙基)-1H-吲哚-7-甲酰胺 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以1.01 g的产率得到5-<2-<(5-chloro-2-methoxybenzoyl)amino>-1-hydroxyethyl>-1H-indole-7-carboxamide
  参考文献：
  名称：

  Rimele; Caggiano; Buckley, Arzneimittel-Forschung/Drug Research, 1989, vol. 39, # 2, p. 187 - 195

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰基-5-(氯乙酰基)二氢吲哚 在 palladium on activated charcoal 吡啶 、 盐酸 、 potassium cyanide 、 manganese(IV) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 tetrafluoroboric acid 、 双氧水 、 硝酸 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， -5.0~60.0 ℃ 、101.33 kPa 条件下， 反应 26.58h， 生成 5-(1-羟基-2-氨基乙基)-1H-吲哚-7-甲酰胺
  参考文献：
  名称：

  Indole-phenol-bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analog of labetalol

  摘要：

  The synthesis of 5-[hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-7- carboxamide, 5, a pyrrolo analogue of labetalol, is described. Compound 5 was found to reduce blood pressure in spontaneously hypertensive rats with an ED50 of 5 mg/kg po, without causing any decrease in heart rate. Isolated tissue studies with 5 shows that it is a nonselective beta-adrenoceptor antagonist and that it is a weaker alpha-adrenoceptor antagonist with a relative selectivity for alpha 1-receptors. Additionally, the compound displayed significant beta-adrenoceptor intrinsic sympathomimetic activity. Evidence is presented that the beta-adrenoceptor antagonist and agonist properties of 5 are mediated via hydrogen-bond formation with the receptor.

  DOI：

  10.1021/jm00156a019

文献信息

• 5-Indolyl substituted aminoethanols
  申请人：American Home Products Corp.

  公开号：US04521606A1

  公开（公告）日：1985-06-04

  Herein is disclosed bicyclic-substituted aminoethanol derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for treating hypertension in a mammal.

  本文披露了双环取代氨基乙醇衍生物，其治疗可接受的酸盐，其制备过程，衍生物的使用方法和制药组合物。这些衍生物可用于治疗哺乳动物的高血压。
• Cyclic amine phenyl beta-3 adrenergic receptor agonists
  申请人：——

  公开号：US20020028835A1

  公开（公告）日：2002-03-07

  This invention provides compounds of Formula I having the structure 1 wherein, R 1 , R 2 , R 3 , R 4 , R 5 , T, T 1 , T 2 , and X are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  本发明提供了具有结构1的化合物，其中R1、R2、R3、R4、R5、T、T1、T2和X如前所定义，或其药学上可接受的盐，其在治疗或抑制与胰岛素抵抗或高血糖有关的代谢紊乱（通常与肥胖或葡萄糖不耐症有关）、动脉粥样硬化、胃肠道疾病、神经遗传性炎症、青光眼、眼压增高和频繁排尿方面非常有用；尤其适用于治疗或抑制2型糖尿病。
• 5(Indolyl) and 5(2,3-dihydroindolyl) substituted aminoethanols and their
  申请人：American Home Products Corporation

  公开号：US04562200A1

  公开（公告）日：1985-12-31

  Herein is disclosed bicyclic-substituted aminoethanol derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for treating hypertension in a mammal.

  本发明公开了双环取代的氨基乙醇衍生物及其治疗上可接受的酸盐，其制备方法，使用衍生物的方法和制药组合物。该衍生物可用于治疗哺乳动物的高血压症。
• Bicyclo-heterocyclic nitrogen substituted aminoethanol derivatives
  申请人：American Home Products Corporation

  公开号：US04622399A1

  公开（公告）日：1986-11-11

  Herein is disclosed bicyclic-substituted aminoethanol derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for treating hypertension in a mammal.

  本发明公开了二环取代氨基乙醇衍生物、其治疗上可接受的酸盐、其制备方法、使用该衍生物的方法以及制备药物组合物的方法。该衍生物可用于治疗哺乳动物的高血压。
• Novel (4-Piperidin-1-yl)-phenyl Sulfonamides as Potent and Selective Human β3 Agonists
  作者：Baihua Hu、John Ellingboe、Stella Han、Elwood Largis、Kitae Lim、Michael Malamas、Ruth Mulvey、Chuansheng Niu、Alexander Oliphant、Jeffrey Pelletier、Thiruvikraman Singanallore、Fuk-Wah Sum、Jeff Tillett、Victoria Wong

  DOI：10.1016/s0968-0896(01)00114-6

  日期：2001.8

  A series of novel (4-piperidin-1-yl)-phenyl sulfonamides was prepared and evaluated for their biological activity on the human beta (3)-adrenergic receptor (AR). Replacement of the 3,4-dihydroxyl group of the catechol moiety with 4-hydroxyl-3-methyl sulfonamide on the left-hand side of the compounds resulted in a number of potent full agonists at the beta (3) receptor. Modification of the right-hand side of the compounds by incorporation of a free carboxylic acid resulted in a few potent human beta (3) agonists with low affinities for beta (1)- and beta (2)-ARs. N-Alkyl substitution on the 4-piperidin-1-yl-phenylamine further increased the beta (3) potency while maintaining the selectivity. For example, sulfonamide 48 is a potent full beta (3) agonist (EC50 = 0.004 muM, IA = 1.0) with > 500-fold selectivity over beta (1)- and beta (2)-ARs. (C) 2001 Elsevier Science Ltd. All rights reserved.