3-desoxy-3-cyanonaltrexone | 207732-98-7

• 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: 3-desoxy-3-cyanonaltrexone
• 英文别名: 17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-carbonitrile；(5a)-17-(Cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-carbonitrile；(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a-hydroxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carbonitrile
• CAS: 207732-98-7
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: MWKGWVXYJYQQQA-MBPVOVBZSA-N

物化性质

• 沸点：
  572.2±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-desoxy-3-cyanonaltrexone 在 氯化铵 、 锌 、 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以62%的产率得到(1R,9R,10S)-17-(cyclopropylmethyl)-3,10-dihydroxy-13-oxo-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4-carbonitrile
  参考文献：
  名称：

  WO2006/52710

  摘要：

  公开号：
• 作为产物：
  描述：

  氰化锌 、 17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以61%的产率得到3-desoxy-3-cyanonaltrexone
  参考文献：
  名称：

  [EN] QUATERNARY OPIOID CARBOXAMIDES
  [FR] CARBOXAMIDES OPIOÏDES QUATERNAIRES

  摘要：

  本发明揭示了化合物(A)和(B)的配方。本发明的化合物对于缓解治疗阿片类药物的副作用很有用。

  公开号：

  WO2009023567A1

文献信息

• Syntheses of novel high affinity ligands for opioid receptors
  作者：Mark P. Wentland、Rongliang Lou、Qun Lu、Yigong Bu、Christoph Denhardt、Jin Jin、Rakesh Ganorkar、Melissa A. VanAlstine、Chengyun Guo、Dana J. Cohen、Jean M. Bidlack

  DOI：10.1016/j.bmcl.2009.02.078

  日期：2009.4

  series of novel high affinity opioid receptor ligands have been made whereby the phenolic-OH group of nalbuphine, naltrexone methiodide, 6-desoxonaltrexone, hydromorphone and naltrindole was replaced by a carboxamido group and the furan ring was opened to the corresponding 4-OH derivatives. These furan ring ‘open’ derivatives display very high affinity for μ and κ receptors and much less affinity for δ

  制备了一系列新型高亲和力阿片受体配体，其中纳布啡、纳曲酮甲硫醚、6-去氧纳曲酮、氢吗啡酮和纳曲吲哚的酚羟基被羧酰胺基团取代，呋喃环开环形成相应的 4-羟基衍生物. 这些呋喃环“开放”衍生物对 μ 和 κ 受体显示出非常高的亲和力，而对 δ 的亲和力要低得多。观察到这些目标化合物比相应的环“闭合”羧酰胺具有更高的受体亲和力，这显着加强了我们关于羧酰胺基团生物活性构象的潜在药效团假设。
• Quaternary opioid carboxamides
  申请人：Rensselaer Polytechnic Institute

  公开号：US08263807B2

  公开（公告）日：2012-09-11

  Compounds of formulas: are disclosed. The compounds are useful for ameliorating the side effects of therapeutic opiates.

  公式为的化合物被披露。这些化合物对于改善治疗鸦片副作用是有用的。
• QUATERNARY OPIOID CARBOXAMIDES
  申请人：Wentland Mark P.

  公开号：US20120302594A1

  公开（公告）日：2012-11-29

  Compounds of formulas: are disclosed. The compounds are useful for ameliorating the side effects of therapeutic opiates.

  公式为的化合物被披露。这些化合物可用于改善治疗阿片类药物的副作用。
• Syntheses and opioid receptor binding properties of carboxamido-substituted opioids
  作者：Mark P. Wentland、Rongliang Lou、Qun Lu、Yigong Bu、Melissa A. VanAlstine、Dana J. Cohen、Jean M. Bidlack

  DOI：10.1016/j.bmcl.2008.10.134

  日期：2009.1

  A series of 15 novel opioid derivatives were made where the prototypic phenolic-OH group of traditional opioids was replaced by a carboxamido (CONH2) group. For 2,6-methano-3-benzazocines and morphinans similar or, in a few instances, enhanced affinity for mu, delta and kappa opioid receptors was observed when the OH --> CONH2 switch was applied. For 4,5 alpha-epoxymorphinans, binding affinities for the corresponding carboxamide derivatives were much lower than the OH partner consistent with our pharmacophore hypothesis concerning carboxamide bioactive conformation. The active metabolite of tramadol and its carboxamide counterpart had comparable affinities for the three receptors. (C) 2008 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide
  作者：Hitoshi Kubota、Kenner C. Rice

  DOI：10.1016/s0040-4039(98)00414-6

  日期：1998.5

  We examined the palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide using 2-methoxyphenyl trifluoromethanesulfonate (4) as a model compound The reaction with two equivalents of Zn(CN)(2) and catalytic Pd(PPh3)(4) in DMF at 120 degrees C for 2 hr afforded 2-methoxybenzonitrile (5)in 81% yield. The synthesis of 3-cyano-3-desoxynaltrexone(3), which had not previouly been obtained by the reaction with potassium or sodium cyanid: as a cyanide source, was achieved by applying this procedure to its corresponding triflate 2. Published by Elsevier Science Ltd.