17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxymorphinan-6-spiro-2'-(1',3'-dioxolane) | 220556-50-3

• 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: 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxymorphinan-6-spiro-2'-(1',3'-dioxolane)
• 英文别名: 17-cyclopropylmethyl-4,5α-epoxy-14-hydroxymorphinan-6-spiro-2'-dioxolane；(4'R,4'aS,7'aR,12'bS)-3'-(cyclopropylmethyl)spiro[1,3-dioxolane-2,7'-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline]-4'a-ol
• CAS: 220556-50-3
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: QKKSNAXUXLEEAR-AYWYSENESA-N

物化性质

• 沸点：
  537.6±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxymorphinan-6-spiro-2'-(1',3'-dioxolane) 在 吡啶 、 氯化亚砜 作用下， 以73%的产率得到17-cyclopropylmethyl-8,14-didehydro-4,5α-epoxymorphinan-6-spiro-2'-(1',3'-dioxolane)
  参考文献：
  名称：

  Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists

  摘要：

  The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the delta opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the 8 receptor over the mu receptor than the corresponding SN-28 derivatives with the 3-hydroxy group (SN-11, 23, 28). Derivatives with the 4-hydroxy group showed potent agonist activities for the 5 receptor in the [S-35]GTPyS binding assay. Although the 17-cyclopropylmethyl derivative (SN-11) with a 3-hydroxy group showed the lowest selectivity for the delta receptor among the morphinan derivatives, the agonist activity toward the delta receptor was the most potent for candidates with the 3-hydroxy group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.047
• 作为产物：
  描述：

  17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-3-[(1-phenyl-1H-tetrazol-5-yl)oxy]-morphinan-6-one 在 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 32.0h， 生成 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxymorphinan-6-spiro-2'-(1',3'-dioxolane)
  参考文献：
  名称：

  Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists

  摘要：

  The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the delta opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the 8 receptor over the mu receptor than the corresponding SN-28 derivatives with the 3-hydroxy group (SN-11, 23, 28). Derivatives with the 4-hydroxy group showed potent agonist activities for the 5 receptor in the [S-35]GTPyS binding assay. Although the 17-cyclopropylmethyl derivative (SN-11) with a 3-hydroxy group showed the lowest selectivity for the delta receptor among the morphinan derivatives, the agonist activity toward the delta receptor was the most potent for candidates with the 3-hydroxy group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.047

文献信息

• Synthesis and Biological Evaluation of 14-Alkoxymorphinans. 16. 14-O-Alkyl Derivatives of the m-Opioid Receptor Antagonist Cyprodime
  作者：Helmut Schmidhammer、Roland Krassnig、Elisabeth Greiner、John R. Traynor

  DOI：10.3987/com-98-s60

  日期：——

  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.