1-{4-[2-(环丙基甲氧基)-乙基]-苯氧基}-2,3-环氧丙烷 | 63659-17-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1-{4-[2-(环丙基甲氧基)-乙基]-苯氧基}-2,3-环氧丙烷
• 中文别名: 倍他洛尔中间体二
• 英文名称: 1-[2-(cyclopropyl-methoxy)-ethyl]-4-(2,3-epoxypropoxy)-benzene
• 英文别名: 1-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-2,3-epoxypropan；1-<4-<(cyclopropylmethoxy)ethyl>phenoxy>-2,3-epoxypropane；<4-(cyclopropylmethoxy)ethyl>phenyl (2,3-epoxy)propyl ether；1-<4-(2-cyclopropylmethoxyethyl)phenoxy>-2,3-epoxypropane；1,2-epoxy-3-(p-cyclopropylmethyloxyethylphenyloxy)propane；2-[4-(2-cyclopropylmethoxyethyl)phenoxymethyl]oxirane；2-((4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)methyl)oxirane；2-[[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]methyl]oxirane
• CAS: 63659-17-6
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: DQRZXLUCRJNWKV-UHFFFAOYSA-N

物化性质

• 沸点：
  358℃
• 密度：
  1.135
• 闪点：
  121℃
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2910900090

反应信息

• 作为反应物：
  描述：

  1-{4-[2-(环丙基甲氧基)-乙基]-苯氧基}-2,3-环氧丙烷 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以80%的产率得到1-chloro-3-<4-(2-cyclopropylmethoxy)ethyl>phenoxypropan-2-ol
  参考文献：
  名称：

  Di Bono; Scilimati, Synthesis, 1995, # 6, p. 699 - 702

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-苯甲氧基苯基)乙醇 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 25.0~60.0 ℃ 、344.73 kPa 条件下， 反应 30.0h， 生成 1-{4-[2-(环丙基甲氧基)-乙基]-苯氧基}-2,3-环氧丙烷
  参考文献：
  名称：

  Synthesis of a series of compounds related to betaxolol, a new .beta.1-adrenoceptor antagonist with a pharmacological and pharmacokinetic profile optimized for the treatment of chronic cardiovascular diseases

  摘要：

  A series of para-substituted phenoxypropanolamines has been synthesized and tested for beta-adrenoceptor blocking activity. Some derivatives (8, 11, 12, 20, 21) exhibited greater in vitro potency than the reference drugs metoprolol and propranolol. This series, in contrast to propranolol but similar to metoprolol, possesses cardioselectivity. The 3-[p-[(cycloalkylmethoxy)ethyl]phenoxy]-1-substituted-amino-2-prop anol derivatives 8 (cyclopropylmethoxyethyl: betaxolol) and 11 (cyclobutylmethoxyethyl) produced antihypertensive effects in spontaneously hypertensive rats. Betaxolol (Kerlon, 8) was found to exhibit an appropriate preclinical pharmacological and human pharmacokinetic profile (elevated oral bioavailability and prolonged plasma half-life) for the treatment of chronic cardiovascular diseases such as hypertension and angina.

  DOI：

  10.1021/jm00389a008
• 作为试剂：
  描述：

  1-{4-[2-(环丙基甲氧基)-乙基]-苯氧基}-2,3-环氧丙烷 、 6-<4-<3-(benzylamino)propionamido>phenyl>-5-methyl-4,5-dihydro-3(2H)-pyridazinone hydrobromide 在 1-{4-[2-(环丙基甲氧基)-乙基]-苯氧基}-2,3-环氧丙烷 作用下， 以38的产率得到6-<4-<3-phenoxy>-2-hydroxypropyl>amino>propionamido>phenyl>-5-methyl-4,5-dihydro-3(2H)-pyridazinone
  参考文献：
  名称：

  J. Med. Chem. 1988, 31, 345-351

  摘要：

  DOI：

文献信息

• Design and synthesis of a series of combined vasodilator-.beta.-adrenoceptor antagonists based on 6-arylpyridazinones
  作者：R. A. Slater、W. Howson、G. T. G. Swayne、E. M. Taylor、D. R. Reavill

  DOI：10.1021/jm00397a013

  日期：1988.2

  synthesized and evaluated as combined vasodilator/beta-adrenoceptor antagonists and potential antihypertensive agents. Many of the early compounds displayed an unacceptably high level of intrinsic sympathomimetic activity (ISA) and a relatively short duration of action. Disubstitution in the 2,3-positions or in the 4-position of the aryloxy ring gave compounds with low ISA levels and, in some instances,

  已经合成了一系列新的6- [4-[[（（芳氧基）酰基]氨基]苯基] -4,5-二氢吡啶并酮，并被评估为血管扩张剂/β-肾上腺素能受体拮抗剂和潜在的降压药。许多早期化合物显示出高水平的固有拟交感神经活性（ISA）和相对较短的作用时间。在芳氧基环的2，3-位或4-位二取代得到的化合物具有较低的ISA水平，并且在某些情况下改善了作用时间。所有这些化合物都是血管扩张药，但5-甲基哒嗪酮衍生物的抗高血压活性始终高于其5-H较低的同系物。
• Vasodilators and .beta.-adrenoceptor antagonists
  申请人：Smith Kline & French Laboratories Ltd.

  公开号：US04652563A1

  公开（公告）日：1987-03-24

  This invention relates to dihydropyridazinone compounds having a cyclopropylmethoxyethyl group in the 6-substituent. These compounds are vasodilators and .beta.-adrenoceptor antagonists. A particular compound of the invention is 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy) ethyl)phenoxy]propylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3 (2H)-pyridazinone.

  这项发明涉及具有6-取代物中环丙基甲氧乙基基团的二氢吡啶基酮化合物。这些化合物是血管扩张剂和β-肾上腺素受体拮抗剂。该发明的一种特定化合物是6-[4-[3-[2-羟基-3-[4-(2-(环丙基甲氧基)乙基)苯氧基]丙基氨基]丙酰氨基]苯基]-5-甲基-4,5-二氢-3(2H)-吡啶酮。
• 2-hydroxypropylamino-alkyl-benzimidazoly-5-yl derivatives and their use
  申请人：Dr. Karl Thomae GmbH

  公开号：US05135932A1

  公开（公告）日：1992-08-04

  The invention relates to new 2-hydroxy-n-propylamines of the formula R.sub.1 --O--CH.sub.2 --CHOH--CH.sub.2 --NH--A--R.sub.2 (I) wherein R.sub.1, R.sub.2 and A are defined as in claim 1, the tautomers, enantiomers and acid addition salts thereof, particularly for pharmaceutical use the physiologically acceptable acid addition salts thereof with inorganic or organic acids, which have valuable pharmacological properties, more particularly a simultaneous cardiotonic and .beta.-blocking activity, and the use thereof as pharmaceutical compositions and processes for preparing them.

  该发明涉及新的2-羟基-n-丙基胺，其化学式为R.sub.1 --O--CH.sub.2 --CHOH--CH.sub.2 --NH--A--R.sub.2 (I)，其中R.sub.1、R.sub.2和A如权利要求书中所定义，其互变异构体、对映体和酸盐，特别用于制药用途，其与无机或有机酸形成的生理学上可接受的酸盐，具有有价值的药理学性质，更具体地具有同时心力增强和β-阻滞活性，以及将其用作制药组合物和制备它们的方法。
• Synthesis and biological activity of the four stereoisomers of 6-[4-[3-[[2-hydroxy-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]propyl]amino]-propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone, a combined vasodilator and .beta.-adrenoceptor antagonist
  作者：W. Howson、J. Kitteringham、J. Mistry、M. B. Mitchell、R. Novelli、R. A. Slater、G. T. G. Swayne

  DOI：10.1021/jm00397a014

  日期：1988.2

  beta-adrenergic antagonist activity. This paper describes the synthesis of each of the four possible stereoisomers of 3 and provides clear evidence for the different pharmacological profile of each of the stereoisomers. The RA,SB isomer 3a has an overall profile slightly better than the complete mixture; the other three isomers all show reduced activity as vasodilators and/or beta-adrenergic antagonists.

  6- [4- [3-[[2-羟基-3- [4- [2-（环丙基甲氧基）乙基]苯氧基]丙基]氨基]丙酰胺基]苯基] -5-甲基-4,5-二氢-3（由于结构中包含两个不对称中心，2H）-哒嗪酮（3）由四种立体异构体（即两个外消旋体）的混合物组成。这两个外消旋物的等摩尔混合物显示出血管舒张作用和β-肾上腺素能拮抗剂活性的新型结合。本文描述了3种四种可能的立体异构体的合成，并为每种立体异构体的不同药理特性提供了明确的证据。RA，SB异构体3a的总体特征略好于完整混合物；其他三种异构体均显示出降低的血管扩张剂和/或β-肾上腺素能拮抗剂活性。
• Synthesis and Irreversible β-Adrenergic Blockade with a Bromoacetamido Derivative of Betaxolol
  作者：Nourdine Amlaiky、Gerard Leclerc

  DOI：10.1002/jps.2600741024

  日期：1985.7

  -2-methyl-2-propylamine]-2-propranol (8), which is a derivative of the beta 1-adrenergic agent betaxolol, was synthesized. Compound 8 showed less potent beta-adrenergic blocking activity than betaxolol in an in vitro test with guinea pig tracheal muscle and left atrium but retained high beta 1-selectivity. Irreversible beta-adrenoceptor antagonism of 8 was assessed by the blockade of the isoproterenol response of the

  1- [4-（2-环丙基甲氧基乙基）苯氧基] -3- [1-对-（溴乙酰胺基）-2-甲基-2-丙胺] -2-丙醇（8），其为β1-的衍生物合成肾上腺素药紫杉醇。在豚鼠气管肌肉和左心房的体外测试中，化合物8的有效β-肾上腺素阻断活性低于紫杉醇，但保留了较高的β1-选择性。通过阻断豚鼠心房的异丙肾上腺素反应以及通过对大鼠大脑皮层的配体结合研究，评估了8的不可逆β-肾上腺素受体拮抗作用。