17-Cyclopropylmethyl-3-hydroxy morphinan-6-one | 26989-37-7

• 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: 17-Cyclopropylmethyl-3-hydroxy morphinan-6-one
• 英文别名: 17-Cyclopropylmethyl-3-hydroxy-morphinan-6-one；(1S,9R,10R)-17-(cyclopropylmethyl)-4-hydroxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
• CAS: 26989-37-7
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: WGEOQAZWFGLHIA-SXLOBPIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-Cyclopropylmethyl-3-hydroxy morphinan-6-one 、 亚甲基三苯基膦烷 以 二甲基亚砜 为溶剂， 生成 17-Cyclopropylmethyl-3-hydroxy-6-methylene-morphinan
  参考文献：
  名称：

  17-Cyclobutylmethyl-3-hydroxy-.beta.-methyl-6-methylene morphinane, and

  摘要：

  公开了对应于以下式子的6-亚甲基吗啡酸衍生物化合物：##STR1## 其中R.sub.1和R.sub.3为H或甲基，R.sub.2为环丙基甲基或环丁基甲基。这些化合物可用作混合镇痛剂/麻醉拮抗剂。

  公开号：

  US04259329A1
• 作为产物：
  描述：

  3-methoxymorphinan-6-one hydrochloride 在 氢溴酸 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 17-Cyclopropylmethyl-3-hydroxy morphinan-6-one
  参考文献：
  名称：

  止痛麻醉剂。2. 8-烷基吗啡喃-6-。

  摘要：

  通过将二烷基铜酸锂共轭添加到相应的7,8-二氢-6-烷基中来制备一系列的8-烷基-3-甲氧基-17-甲基吗啡喃-6-（3C）和-异吗啡喃-6-酮（3T）。 2C和2T。这些17-甲基化合物是有效的镇痛药，并通过用环烷基甲基部分取代17-甲基而转化为混合的麻醉激动剂-拮抗剂7-10。8个取代基改变了观察到的活性类型。这些化合物之一，即17-（环丁基甲基）-3-羟基-8β-甲基吗啡喃-6-（10Ca）的激动剂与拮抗剂之比为0.1。化合物10Ca在大鼠中不支持或不引起依赖性。然而，该化合物似乎是吗啡依赖性猴子中的典型麻醉剂。

  DOI：

  10.1021/jm00176a013

文献信息

• 17-Cycloalkylmethyl-6-methylene-morphinane-derivatives
  申请人：MILES LABORATORIES, INC.

  公开号：EP0027925A1

  公开（公告）日：1981-05-06

  Disclosed are 6-methylene, morphinan compounds corresponding to the formula: wherein R1 und R3 are H or methyl and R2 is cyclopropylmethyl or cyclobutylmethyl. These compounds are useful as mixed analgesics/narcotic antagonists.

  所公开的 6-亚甲基吗啡烷化合物符合以下式子： 其中 R1 和 R3 为 H 或甲基，R2 为环丙基甲基或环丁基甲基。这些化合物可用作混合镇痛剂/麻醉拮抗剂。
• Synthesis and Pharmacological Evaluation of Aminothiazolomorphinans at the Mu and Kappa Opioid Receptors
  作者：Brian A. Provencher、Anna W. Sromek、Wei Li、Shayla Russell、Elena Chartoff、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm401290y

  日期：2013.11.14

  Previous studies with aminothiazolomorphinans suggested that this class of opioid ligands may be useful as a potential pharmacotherapeutic to decrease drug abuse. Novel aminothiazole derivatives of cyclorphan were prepared to evaluate a series of aminothiazolomorphinans with, varying pharmacological properties at the kappa opioid receptor (KOR) and mu opioid receptor (MOR). This study was focused on exploring the regioisomeric analogs with the aminothiazole on the C-ring of the morphinan skeleton. Receptor binding and [S-35]GTP gamma S binding assays were used to characterize the affinity and pharmacological properties of the aminothiazolomorphinans. Intracranial self-stimulation (ICSS) was used to compare the effects of a representative aminothiazolomorphinan with the morphinan mixed-KOR/MOR agonist butorphan (MCL-101) on brain-stimulation reward.
• Analgesic narcotic antagonists. 9. 6-Methylene-8.beta.-alkyl-N-(cycloalkylmethyl)-3-hydroxy- or -methoxymorphinans
  作者：Joseph O. Polazzi、Michael P. Kotick、John F. Howes、Ann R. Bousquet

  DOI：10.1021/jm00144a029

  日期：1981.12

  Series of N-(cyclopropylmethyl) (P series) or N-(cyclobutylmethyl) (B series) 3-methoxy (1) or 3-hydroxy (2) morphinan-6-ones with hydrogen (a), methyl (b), or ethyl (c) groups in the 8 beta position were converted to the 6-methylene compounds 3 or 4 by reaction with Ph3P = CH2. One member of this new series, N-(cyclobutylmethyl)-8 beta-methyl-6-methylenemorphinan-3-ol (4Bb), had potent mixed agonist-narcotic antagonist properties and, in contrast to the previously studied 6-oxo compound 2Bb, did not substitute for morphine in dependent rats or monkeys.
• Nitrogen Containing Morphinan Derivatives and the Use Thereof
  申请人：Purdue Pharma L.P.

  公开号：US20140171461A1

  公开（公告）日：2014-06-19

  The application is directed to compounds of Formula I-A and pharmaceutically acceptable salts and solvates thereof, wherein R 1a -R 3a , R 4 , Y, and Z are defined as set forth in the specification. The invention is also directed to use of compounds of Formula I-A to treat disorders responsive to the modulation of one or more opioid receptors, or as synthetic intermediates. Certain compounds of the present invention are especially useful for treating pain.
• US4230712A
  申请人：——

  公开号：US4230712A

  公开（公告）日：1980-10-28