(1′S,5α,6R,7R,14α)-1′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethanomorphinan-7-yl)-1′-(3-chlorophenyl)ethan-1′-ol | 1417783-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (1′S,5α,6R,7R,14α)-1′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethanomorphinan-7-yl)-1′-(3-chlorophenyl)ethan-1′-ol
• 英文别名: (1’S,5α,6R,7R,14α)-1'-(3-chlorophenyl)-1'-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethanomorphinan-7-yl)ethan-1'-ol；(1'S,5α,6R,7R,14α)-1'-(3-chlorophenyl)-1'-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethanomorphinan-7-yl)-ethan-1'-ol；BU10098；(1S,2S,6R,14R,15R,16R)-16-[(1S)-1-(3-chlorophenyl)-1-hydroxyethyl]-5-(cyclopropylmethyl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
• CAS: 1417783-67-5
• 化学式: C₃₁H₃₆ClNO₄
• 分子量: 522.084
• InChiKey: YFBHWYAQYNXSFZ-JTTXIWGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 六甲基磷酰三胺 、 丙烷-1-硫醇 、 sodium hydride 作用下， 反应 3.0h， 生成 (1′S,5α,6R,7R,14α)-1′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethanomorphinan-7-yl)-1′-(3-chlorophenyl)ethan-1′-ol
  参考文献：
  名称：

  Selectively Promiscuous Opioid Ligands: Discovery of High Affinity/Low Efficacy Opioid Ligands with Substantial Nociceptin Opioid Peptide Receptor Affinity

  摘要：

  Emerging clinical and preclinical evidence suggests that a compound displaying high affinity for mu, K, and delta opioid (MOP, KOP, and DOP) receptors and antagonist activity at each, coupled with moderate affinity and efficacy at nociceptin opioid peptide (NOP) receptors will have utility as a relapse prevention agent for multiple types of drug abuse. Members of the orvinol family of opioid ligands have the desired affinity profile but have typically displayed substantial efficacy at MOP and or KOP receptors. In this study it is shown that a phenyl ring analogue (1d) of buprenorphine displays the desired profile in vitro with high, nonselective affinity for the MOP, KOP, and DOP receptors coupled with moderate affinity for NOP receptors. In vivo, Id lacked any opioid agonist activity and was an antagonist of both the MOP receptor agonist morphine and the KOP receptor agonist ethylketocydazocine, confirming the desired opioid receptor profile in vivo.

  DOI：

  10.1021/jm401964y

文献信息

• ORVINOL AND THEVINOL DERIVATIVES USEFUL IN THE TREATMENT OF DRUG AND ALCOHOL ABUSE
  申请人：Lewis John

  公开号：US20140213603A1

  公开（公告）日：2014-07-31

  The invention provides orvinol and thevinol compounds useful for the treatment of drug and alcohol abuse, the compounds being particularly useful for the prevention of relapse in recovering addicts.

  这项发明提供了用于治疗药物和酒精滥用的奥维诺尔（orvinol）和西维诺尔（thevinol）化合物，这些化合物特别适用于预防康复成瘾者的复发。
• Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse, depression, anxiety, or a compulsive disorder
  申请人：The University of Bath

  公开号：US10030031B2

  公开（公告）日：2018-07-24

  The invention provides a method of treating drug and alcohol abuse, depression, anxiety, or a compulsive disorder in a subject comprising administering to the subject a compound having the formula: or a pharmaceutically acceptable salt or solvate thereof, wherein R, R1, R2, R3, R4, R5, and X are as defined in the specification.

  本发明提供了一种治疗吸毒和酗酒、抑郁、焦虑或强迫症的方法，该方法包括向受试者施用一种具有以下式子的化合物： 或其药学上可接受的盐或溶液，其中 R、R1、R2、R3、R4、R5 和 X 如说明书中所定义。
• Orvinol and Thevinol Derivatives Useful in the Treatment of Drug and Alcohol Abuse
  申请人：The University of Bath

  公开号：US20150202200A1

  公开（公告）日：2015-07-23

  The invention provides orvinol and thevinol compounds useful for the treatment of drug and alcohol abuse, the compounds being particularly useful for the prevention of relapse in recovering addicts.
• Orvinol and Thevinol Derivatives Useful in the Treatment of Anxiety or a Compulsive Disorder
  申请人：The University of Bath

  公开号：US20160136151A1

  公开（公告）日：2016-05-19

  The invention provides a method of treating anxiety or a compulsive disorder in a subject comprising administering to the subject a compound having formula 2: or a pharmaceutically acceptable salt or solvate thereof, wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , and X are as defined in the specification.
• Orvinol and Thevinol Derivatives Useful in the Treatment of Drug and Alcohol Abuse, Depression, Anxiety, or a Compulsive Disorder
  申请人：The University of Bath

  公开号：US20170044173A1

  公开（公告）日：2017-02-16

  The invention provides a method of treating drug and alcohol abuse, depression, anxiety, or a compulsive disorder in a subject comprising administering to the subject a compound having formula 2 : or a pharmaceutically acceptable salt or solvate thereof, wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , and X are as defined in the specification.