4-[(2S)-oxiranylmethoxy]-2-oxindole | 392690-82-3

• 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: 4-[(2S)-oxiranylmethoxy]-2-oxindole
• 英文别名: 4-[[(2S)-oxiran-2-yl]methoxy]-1,3-dihydroindol-2-one
• CAS: 392690-82-3
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: QPBYYTKPYJRYKF-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2S)-oxiranylmethoxy]-2-oxindole 、 1-[4-(4-Aminomethyl-piperidine-1-sulfonyl)-phenyl]-3-octyl-urea 以 甲醇 为溶剂， 生成 1-[4-(4-{[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-4-yloxy)-propylamino]-methyl}-piperidine-1-sulfonyl)-phenyl]-3-octyl-urea
  参考文献：
  名称：

  Novel substituted 4-aminomethylpiperidines as potent and selective human β3-agonists. Part 1: aryloxypropanolaminomethylpiperidines

  摘要：

  The synthesis and SAR of a series of human beta(3) adrenoreceptor agonists based on a template derived from a common pharmacophore coupled with 4-aminomethylpiperidine is described. Potent and selective agents were identified such as 26 that was in vitro active in CHO cells expressing human beta(3)-AR (EC50 = 49 nNl, IA = 1.1), and in vivo active in a transgenic mouse model. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00607-8
• 作为产物：
  描述：

  (2-甲氧基-6-硝基苯基)乙腈 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢溴酸 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 4-[(2S)-oxiranylmethoxy]-2-oxindole
  参考文献：
  名称：

  Novel substituted 4-aminomethylpiperidines as potent and selective human β3-agonists. Part 1: aryloxypropanolaminomethylpiperidines

  摘要：

  The synthesis and SAR of a series of human beta(3) adrenoreceptor agonists based on a template derived from a common pharmacophore coupled with 4-aminomethylpiperidine is described. Potent and selective agents were identified such as 26 that was in vitro active in CHO cells expressing human beta(3)-AR (EC50 = 49 nNl, IA = 1.1), and in vivo active in a transgenic mouse model. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00607-8

文献信息

• Substituted 2- (S) -hydroxy-3- (piperidin-4-yl-methylamino) -propyl ethers and substituted 2-aryl-2- (R) - hydroxy-1- (piperidin-4-yl-methyl) -ethylamine beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020037907A1

  公开（公告）日：2002-03-28

  This invention provides compounds of Formula I having the structure 1 wherein A, B, Z, R and R 1 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.

  这项发明提供了具有结构式1的化合物，其中A、B、Z、R和R1如前文所定义，或其药学上可接受的盐，用于治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖不耐受有关）、动脉粥样硬化、胃肠道疾病、神经炎症、青光眼、眼压增高和频繁排尿；特别适用于治疗或抑制2型糖尿病。
• Substituted 2-(S)-hydroxy-3-(piperidin-4-yl-methylamino)-propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)-ethylamine &bgr;-3 adrenergic receptor agonists
  申请人：Wyeth

  公开号：US06506901B2

  公开（公告）日：2003-01-14

  This invention provides compounds of Formula I having the structure wherein A, B, Z, R and R1 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.

  本发明提供具有式I的化合物，其结构中A、B、Z、R和R1如前所定义，或其药学上可接受的盐，这些化合物在治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖耐受性不良有关）、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；并且在治疗或抑制II型糖尿病方面特别有用。
• Potent oxindole based human β3 adrenergic receptor agonists
  作者：F. Craig Stevens、William E. Bloomquist、Anthony G. Borel、Marlene L. Cohen、Christine A. Droste、Mark L. Heiman、Aidas Kriauciunas、Daniel J. Sall、Frank C. Tinsley、Cynthia D. Jesudason

  DOI：10.1016/j.bmcl.2007.09.011

  日期：2007.11

  The synthesis and biological evaluation of a series of oxindole beta(3) adrenergic receptor agonists is described. A modulation of rat atrial tachycardia was observed with substitution at the 3-position of the oxindole moiety. (C) 2007 Elsevier Ltd. All rights reserved.
• US6506901B2
  申请人：——

  公开号：US6506901B2

  公开（公告）日：2003-01-14
• [EN] SUBSTITUTED 2-(S)-HYDROXY-3-(PIPERIDIN-4-YL-METHYLAMINO)-PROPYL ETHERS AND SUBSTITUTED 2-ARYL-2-(R)-HYDROXY-1-(PIPERIDIN-4-YL-METHYL)-ETHYLAMINE BETA-3 ADRENERGIC RECEPTOR AGONISTS<br/>[FR] AGONISTES VIS-A-VIS DE RECEPTEUR ADRENERGIQUE BETA 3 DE 2-(S)-HYDROXY-3-(PIPERIDINE-4-YL-METHYLAMINO)-PROPYL ETHERS SUBSTITUES ET DE 2-ARYL-2-(R)-HYDROXY-1-(PIPERIDINE-4-YL-METHYL)-ETHYLAMINE SUBSTITUEE
  申请人：AMERICAN HOME PROD

  公开号：WO2002006255A2

  公开（公告）日：2002-01-24

  The invention provides compounds of Formula (I) having the structure wherein A, B, Z, R and R1 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.