MCL-111 | 116597-85-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: MCL-111
• 英文别名: 17-benzyl-morphinan-3-ol；(1R,9R,10R)-17-benzyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
• CAS: 116597-85-4
• 化学式: C₂₃H₂₇NO
• 分子量: 333.473
• InChiKey: RWLNQUZNBYIVJE-MDNUFGMLSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  497.7±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  左啡诺 在 盐酸 、 sodium hydroxide 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 MCL-111
  参考文献：
  名称：

  Mixed κ agonists and μ agonists/Antagonists as potential pharmacotherapeutics for cocaine abuse: synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan

  摘要：

  A series of new N-substituted derivatives of morphinan was synthesized and their binding affinity for the three opioid receptors (mu, delta, and kappa) was determined. A paradoxical effect of N-propargyl (MCL-117) and N-(3-iodoprop-(2E)-enyl) (MCL-118) substituents on the binding affinities for the mu and kappa opioid receptors was observed. All of these novel derivatives showed a preference for the mu and kappa versus delta binding. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00543-1

文献信息

• Hydroxy-morphinane. 7. Mitteilung. (−)-3-Hydroxy-N-allyl-morphinan und verwandte Verbindungen
  作者：J. Hellerbach、A. Grüssner、O. Schnider

  DOI：10.1002/hlca.19560390212

  日期：——

  1-(p-Hydroxybenzyl)-1, 2,3,4,5,6,7,8-octahydro-isoquinoline has been resolved into the optical antipodes, from which any desired optically active 3-hydroxy-morphinan substituted at the nitrogen atom can easily be obtained. The (-)-3-hydroxy-N-allyl-morphinan thus obtained as well as its ethers and ester counteract the effect of opiates and other potent narcotics. Given in adequate small doses they

  1-（对羟基苄基）-1，2,3,4,5,6,7,8-八氢异喹啉已拆分成旋光对映体，氮上取代了任何所需的旋光3-羟基吗啡喃原子很容易获得。如此获得的（-）-3-羟基-N-烯丙基吗啡及其醚和酯抵消了鸦片剂和其他有效麻醉剂的作用。给予足够的小剂量，它们能够缓解不良的副作用。
• Mixed κ agonists and μ agonists/Antagonists as potential pharmacotherapeutics for cocaine abuse: synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan
  作者：John L Neumeyer、Xiao-Hui Gu、L.Alexander van Vliet、Nicholas J DeNunzio、Daniela E Rusovici、Dana J Cohen、S.Stevens Negus、Nancy K Mello、Jean M Bidlack

  DOI：10.1016/s0960-894x(01)00543-1

  日期：2001.10

  A series of new N-substituted derivatives of morphinan was synthesized and their binding affinity for the three opioid receptors (mu, delta, and kappa) was determined. A paradoxical effect of N-propargyl (MCL-117) and N-(3-iodoprop-(2E)-enyl) (MCL-118) substituents on the binding affinities for the mu and kappa opioid receptors was observed. All of these novel derivatives showed a preference for the mu and kappa versus delta binding. (C) 2001 Elsevier Science Ltd. All rights reserved.