MCL-117 | 736-76-5

• 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-117
• 英文别名: 17-prop-2-ynyl-morphinan-3-ol；17-Prop-2-inyl-morphinan-3-ol；(-)3-hydroxy-N-propargylmorphinan；(1R,9R,10R)-17-prop-2-ynyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
• CAS: 736-76-5
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: OKICQDFBWUMTDE-QXAKKESOSA-N

物化性质

• 熔点：
  198-200 °C(Solv: ethanol (64-17-5))
• 沸点：
  441.0±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)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  MCL-117 在 氢溴酸 作用下， 生成 17-(3ξ-bromo-allyl)-morphinan-3-ol
  参考文献：
  名称：

  羟基吗啡喃。第七次沟通。（-）-3-羟基-N-烯丙基吗啡喃及相关化合物

  摘要：

  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。

  DOI：

  10.1002/hlca.19560390212
• 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-117
  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

• Synthesis and Preliminary In vitro Investigation of Bivalent Ligands Containing Homo- and Heterodimeric Pharmacophores at μ, δ, and κ Opioid Receptors
  作者：Xuemei Peng、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm050577x

  日期：2006.1.1

  A series of homo- and heterodimeric ligands containing kappa agonist and mu agonist/antagonist pharmacophores joined by a linker chain of varying lengths was synthesized and evaluated in vitro by their binding affinity at mu, delta, and kappa opioid receptors. The functional activities of these compounds were measured in the [S-35]- GTP gamma S binding assay. The data suggest that the stereochemistry of the pharmacophores, the N-substituents of the pharmacophore, ester linkages, and the spacer length were crucial factors for optimum interactions of such ligands at opioid receptor binding sites. These novel ligands as well as their pharmacological properties will serve as the basis for our continuing investigation of such bivalent ligands as probes of the opioid receptor oligomerization phenomena and for in vivo studies as analgesics.
• US2740788
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• DE951722
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