3,14β-bis(benzyloxy)-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-6-one | 220556-55-8

• 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: 3,14β-bis(benzyloxy)-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-6-one
• 英文别名: 3,14-dibenzyloxy-17-cyclopropylmethyl-4,5α-epoxymorphinan-6-one；3,14β-dibenzyloxy-17-cyclopropylmethyl-4,5α-epoxy-morphinan-6-one；17-cyclopropylmethyl-4,5α-epoxy-3-benzyloxy-14-benzyloxymorphinan-6-one；17-Cyclopropylmethyl-4,5alpha-epoxy-3-benzyloxy-14-benzyloxymorphinan-6-one；(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-bis(phenylmethoxy)-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 220556-55-8
• 化学式: C₃₄H₃₅NO₄
• 分子量: 521.656
• InChiKey: MGVNXSVXMJXVIW-ODRDEDCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,14β-bis(benzyloxy)-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-6-one 在 钯 氢气 、 甲醇 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.58h， 以to give 4 (165 mg, 91%) as a yellow gum的产率得到14β-(benzyloxy)-17-(cyclopropylmethyl)-4,5α-epoxy-3-hydroxymorphinane-6-one
  参考文献：
  名称：

  N-Oxides of 4,5-Epoxy-Morphinanium Analogs

  摘要：

  本发明公开了4,5-环氧-吗啡铵类似物的新型N-氧化物。本发明还公开了含有4,5-环氧-吗啡铵类似物的N-氧化物的制药组合物及其制药用途的方法。公开的化合物可用作阿片受体调节剂等用途。

  公开号：

  US20080234306A1
• 作为产物：
  描述：

  盐酸纳曲酮 在 盐酸 、 三氟甲磺酸 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 Petroleum ether 为溶剂， 反应 22.0h， 生成 3,14β-bis(benzyloxy)-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-6-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 14-Alkoxymorphinans. 16. 14-O-Alkyl Derivatives of the m-Opioid Receptor Antagonist Cyprodime

  摘要：

  The 14-O-benzyl derivatives of cyprodime and 3-hydroxycyprodime (compounds (5) and (6), respectively) were synthesized in several steps from 3-desoxynaltrexone (2a) and naltrexone (2), respectively. In the mouse vas deferens preparation it was found that a 14-O-benzyl group could enhance mu opioid receptor affinity in cyprodime while the mu affinity of 3-hydroxycyprodime was not changed.

  DOI：

  10.3987/com-98-s60

文献信息

• [EN] N-OXIDES OF 4,5-EPOXY-MORPHINANIUM ANALOGS<br/>[FR] N-OXYDES D'ANALOGUES 4,5-ÉPOXY-MORPHINANIUM
  申请人：PROGENICS PHARM INC

  公开号：WO2009067275A1

  公开（公告）日：2009-05-28

  Novel N-oxides of 4,5-epoxy-morphinanIum analogs are disclosed. Pharmaceutical compositions containing the N-oxides of 4,5-epoxy-morphinanium analogs and methods of their pharmaceutical uses are also disclosed. The compounds disclosed are useful, inter alia, as modulators of opioid receptors.

  揭示了4,5-环氧吗啡啉盐类的新型N-氧化物。还揭示了含有4,5-环氧吗啡啉盐类的N-氧化物的药物组合物，以及它们的药用方法。所揭示的化合物可用作阿片受体调节剂等用途。
• Synthesis and Biological Evaluation of 14-Alkoxymorphinans. Part 19
  作者：Falko Schüllner、Ruth Meditz、Roland Krassnig、Günther Morandell、Valery N. Kalinin、Ellen Sandler、Mariana Spetea、Angela White、Helmut Schmidhammer、Ilona P. Berzetei-Gurske

  DOI：10.1002/hlca.200390187

  日期：2003.7

  The 14-O-benzylnaltrexones 3–6 were prepared from naltrexone (2) in several steps. The novel compounds were biologically evaluated in radioligand binding and in [35S]GTPγS functional assays in comparison to the reference compound naltrexone. In the binding assay, compounds 3–6 exhibited preference for κ opioid receptors, while the parent compound naltrexone shows preference for μ receptors. In the

  14- O-苄基纳曲酮3 – 6是由纳曲酮（2）分几步制备的。新化合物在放射性配体结合物的生物评估和[ 35 S] GTP γ š功能测定相比于参考化合物纳曲酮。在结合测定中，化合物3 – 6对κ阿片受体表现出偏爱，而母体化合物纳曲酮对μ受体表现出偏爱。在功能测定中，化合物3 – 6的μ拮抗剂效力在纳曲酮范围内，而κ 与纳曲酮相比，大多数新型化合物的拮抗药效力要高得多。
• Morphinan derivatives the quaternary ammonium salts thereof substituted in position 14, method for production and use thereof
  申请人：Schmidhammer Helmut

  公开号：US20050182258A1

  公开（公告）日：2005-08-18

  The present invention relates to a class of morphinan compounds and quaternary ammonium salts thereof, substituted in Position 14, which may be used as highly active analgesics or also as opioid antagonists. The present invention also relates to the pharmaceutically acceptable salts and easily produced derivatives thereof, a process for the production thereof and use thereof in the production of pharmaceutical specialities.

  本发明涉及一类在14位取代的吗啡型化合物和季铵盐，可用作高效镇痛剂或阿片受体拮抗剂。本发明还涉及药物可接受的盐和易于制备的衍生物，其制备方法及在制备药物专用品中的应用。
• Morphinan derivatives, the quaternary ammonium salts thereof substituted in position 14, method for production and use thereof
  申请人：Schmidhammer Helmut

  公开号：US20080064712A1

  公开（公告）日：2008-03-13

  The present invention relates to a class of morphinan compounds and quaternary ammonium salts thereof, substituted in Position 14, which may be used as highly active analgesics or also as opioid antagonists. The present invention also relates to the pharmaceutically acceptable salts and easily produced derivatives thereof, a process for the production thereof and use thereof in the production of pharmaceutical specialities.

  本发明涉及一类在14位取代的吗啡类化合物和其季铵盐，可用作高效镇痛剂或阿片类拮抗剂。本发明还涉及其药学上可接受的盐和易于制备的衍生物，其制备过程以及在制备药物专业用途中的应用。
• WO2008/70462
  申请人：——

  公开号：——

  公开（公告）日：——