14-O-Ethyl-5-methylnaltrexone | 147847-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 14-O-Ethyl-5-methylnaltrexone
• 英文别名: 17-(cyclopropylmethyl)-4,5α-epoxy-14β-ethoxy-3-hydroxy-5β-methylmorphinan-6-one；14-O-ethyl-5β-methylnaltrexone；(-)-17-(cyclopropylmethyl)-4,5α-epoxy-14β-ethoxy-3-hydroxy-5β-methylmorphinan-6-one；(4R,4aS,7aR,12bR)-3-(cyclopropylmethyl)-4a-ethoxy-9-hydroxy-7a-methyl-1,2,4,5,6,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 147847-14-1
• 化学式: C₂₃H₂₉NO₄
• 分子量: 383.488
• InChiKey: ZQZLDDPHSAAHQV-LMDOGRNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯肼,盐酸盐 、 14-O-Ethyl-5-methylnaltrexone 在 氨 作用下， 以 溶剂黄146 、 水 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Use of opioid receptor antagonist compounds for the prevention and/or treatment of diseases associated with the target calcineurin

  摘要：

  公式为吗啡啶衍生物及其药用盐可用作治疗和/或预防与靶向钙调神经酶相关的疾病的药物。

  公开号：

  EP1595541A1
• 作为产物：
  描述：

  盐酸纳曲酮 在 potassium tert-butylate 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 14-O-Ethyl-5-methylnaltrexone
  参考文献：
  名称：

  A Novel Method for the Introduction of a 5β-Methyl Group into 4,5α-Epoxymorphinan-6-onesvia the Enol Ether

  摘要：

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<380::aid-hlca380>3.0.co;2-v

文献信息

• Synthesis and Biological Evaluation of 14-Alkoxymorphinans. Part 9. 14-O-ethyl-5-methylnaltrexone, and opioid antagonist with unusual selectivity
  作者：Helmut Schmidhammer、Andrea Schratz、Charlotte Schmidt、Dinesh Patel、John R. Traynor

  DOI：10.1002/hlca.19930760131

  日期：1993.2.10

  14O-Ethyl-5m-ethylnaloxone (7) and 14O-ethyl-5-methylnaltrexone (8) have been prepared starting from 14O-ethyl-5-methyloxycodone (9) in several steps. Both, 7 and 8, were found to be opioid antagonists in vitro and in vivo. Compound 7 exhibited some selectivity for μ opioid receptors, whereas compound 8 did not show selectivity for any of the receptor types. In the AcOH-writhing antagonism test, 8

  14 ø -乙基5M-ethylnaloxone（7）和14 ø -乙基-5-甲基纳曲酮（8）已制备的起始从14 ø -乙基-5- methyloxycodone（9在几个步骤中）。既，7和8，被发现是阿片样物质拮抗剂在体外和体内。化合物7对μ阿片样物质受体表现出一定的选择性，而化合物8对任何一种受体类型均不表现出选择性。在对AcOH的拮抗作用测试中，8 不能拮抗吗啡引起的镇痛作用，但可以拮抗芬太尼和舒芬太尼引起的镇痛作用。
• Opioid receptor antagonist compounds
  申请人：Astra AB

  公开号：US06136817A1

  公开（公告）日：2000-10-24

  New morphinane derivatives of the formula ##STR1## their pharmaceutically acceptable salts, a process for their preparation and their use in the manufacture of pharmaceutical preparations.

  新的吗啡啶衍生物的分子式为##STR1##，它们的药用盐，以及用于它们制备和用于制造药物制剂的过程。
• Synthesis and biological evaluation of 14-alkoxymorphinans. 14.1 14-ethoxy-5-methyl substituted indolomorphinans with δ opioid receptor selectivity
  作者：Helmut Schmidhammer、Dietmar Daurer、Martina Wieser、Krisztina Monory、Anna Borsodi、Jackie Elliott、John R. Traynor

  DOI：10.1016/s0960-894x(96)00599-9

  日期：1997.1

  The 5-methyl and 14-ethoxy substituted analogues (compounds 2-4) of the delta opioid receptor antagonist naltrindole showed similar selectivity when compared with the reference drug. Compound 2 was a delta receptor antagonist in the mouse vas deferens preparation (MVD) exhibiting considerably higher selectivity ratios than naltrindole, while compound 4 was found to be a full and potent delta receptor agonist in the MVD. (C) 1997, Elsevier Science Ltd.
• Use of opioid receptor antagonist compounds for the prevention and/or treatment of diseases associated with the target calcineurin
  申请人：ALCASYNN PHARMACEUTICALS GMBH

  公开号：EP1595541A1

  公开（公告）日：2005-11-16

  Morphinane derivatives of the formula their pharmaceutically acceptable salts are provided for use as medicaments for the treatment and/or prevention of disorders associated with the target calcineurin.

  公式为吗啡啶衍生物及其药用盐可用作治疗和/或预防与靶向钙调神经酶相关的疾病的药物。
• A Novel Method for the Introduction of a 5β-Methyl Group into 4,5α-Epoxymorphinan-6-onesvia the Enol Ether
  作者：Roland Krassnig、Helmut Schmidhammer、Klaus Wurst

  DOI：10.1002/(sici)1522-2675(20000216)83:2<380::aid-hlca380>3.0.co;2-v

  日期：2000.2.16