(2E)-N-[(5R,6R)-3-acetamido-17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxymorphinan-6-yl]-3-(furan-3-yl)-N-methylprop-2-enamide | 1092369-49-7

• 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: (2E)-N-[(5R,6R)-3-acetamido-17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxymorphinan-6-yl]-3-(furan-3-yl)-N-methylprop-2-enamide
• 英文别名: (E)-N-[(4R,4aS,7R,7aR,12bS)-9-acetamido-3-(cyclopropylmethyl)-4a-hydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-3-(furan-3-yl)-N-methylprop-2-enamide
• CAS: 1092369-49-7
• 化学式: C₃₀H₃₅N₃O₅
• 分子量: 517.625
• InChiKey: VCGPPQOREQXTHA-QBDBJEPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-酒石酸 、 (2E)-N-[(5R,6R)-3-acetamido-17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxymorphinan-6-yl]-3-(furan-3-yl)-N-methylprop-2-enamide 以 甲醇 为溶剂， 生成 (2E)-N-[(5R,6R)-3-acetamido-17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxymorphinan-6-yl]-3-(furan-3-yl)-N-methylprop-2-enamide tartrate
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship of novel opioid κ-agonists

  摘要：

  By focusing on 4,5-epoxymorphinan, a traditional opioid skeleton but a new structure in the opioid kappa-agonist research field, and by rationally applying the 'message-address concept' and 'accessory site hypothesis,' we discovered a new chemical class opioid kappa- gonist, TRK-820 (1). Its development as an antipruritus is now in the final stage. Here, the full scope of its design, synthesis, and structure-activity relationship are described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.011
• 作为产物：
  描述：

  (2E)-N-[(5R,6R)-3-amino-17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxymorphinan-6-yl]-3-(furan-3-yl)-N-methylprop-2-enamide 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以58%的产率得到(2E)-N-[(5R,6R)-3-acetamido-17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxymorphinan-6-yl]-3-(furan-3-yl)-N-methylprop-2-enamide
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship of novel opioid κ-agonists

  摘要：

  By focusing on 4,5-epoxymorphinan, a traditional opioid skeleton but a new structure in the opioid kappa-agonist research field, and by rationally applying the 'message-address concept' and 'accessory site hypothesis,' we discovered a new chemical class opioid kappa- gonist, TRK-820 (1). Its development as an antipruritus is now in the final stage. Here, the full scope of its design, synthesis, and structure-activity relationship are described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.011