(4bR,8aS,9R)-8a-hydroxy-11-isobutyl-3-methoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one | 1000410-42-3

• 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: (4bR,8aS,9R)-8a-hydroxy-11-isobutyl-3-methoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one
• CAS: 1000410-42-3
• 化学式: C₂₁H₂₉NO₃
• 分子量: 343.466
• InChiKey: MXULUAJRXXAKLE-NJDAHSKKSA-N

物化性质

• 沸点：
  501.8±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4bR,8aS,9R)-8a-hydroxy-11-isobutyl-3-methoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one 、 2-氨基苯甲醛 在 甲烷磺酸 作用下， 以 乙醇 为溶剂， 以70%的产率得到(6R,6aS,14aR)-17-isobutyl-2-methoxy-5,6,7,14-tetrahydro-6aH-6,14a-(epiminoethano)naphtho[2,1-b]acridin-6a-ol
  参考文献：
  名称：

  Design and synthesis of KNT-127, a δ-opioid receptor agonist effective by systemic administration

  摘要：

  We have reported previously the novel delta-opioid agonist, SN-28, which was more potent in in vitro assays than the prototype delta-agonists, TAN-67 and SNC-80. However, when administered by subcutaneous injection, this compound showed no analgesic effect at dosages greater than 30 mg/kg in the acetic acid writhing test. We speculated that SN-28 was not effective in the test because the presence of the charged ammonium groups prevented its penetration through the blood-brain barrier. On the basis of our proposal, we designed the novel delta-agonist, KNT-127, which was effective with systemic administration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.083
• 作为产物：
  描述：

  (1'R,9'R,10'S)-17'-(cyclopropylmethyl)-4'-methoxyspiro[1,3-dioxolane-2,13'-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene]-10'-ol 在 platinum(IV) oxide 、 氢溴酸 、 氢气 作用下， 以 甲醇 为溶剂， 以56%的产率得到(4bR,8aS,9R)-8a-hydroxy-11-isobutyl-3-methoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one
  参考文献：
  名称：

  Design and synthesis of KNT-127, a δ-opioid receptor agonist effective by systemic administration

  摘要：

  We have reported previously the novel delta-opioid agonist, SN-28, which was more potent in in vitro assays than the prototype delta-agonists, TAN-67 and SNC-80. However, when administered by subcutaneous injection, this compound showed no analgesic effect at dosages greater than 30 mg/kg in the acetic acid writhing test. We speculated that SN-28 was not effective in the test because the presence of the charged ammonium groups prevented its penetration through the blood-brain barrier. On the basis of our proposal, we designed the novel delta-agonist, KNT-127, which was effective with systemic administration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.083