N-hexyl-[(5R,6R)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan]-6-amine | 1092442-54-0

• 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: N-hexyl-[(5R,6R)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan]-6-amine
• 英文别名: (4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-7-(hexylamino)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol
• CAS: 1092442-54-0
• 化学式: C₂₆H₃₈N₂O₃
• 分子量: 426.599
• InChiKey: MUHQRFDXYSDWBJ-PUKUCHAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  65
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-hexyl-[(5R,6R)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan]-6-amine 在 盐酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以283.4 mg的产率得到N-hexyl-[(5R,6R)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan]-6-amine dihydrochloride
  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：

  N-[(5R,6R)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-hexanamide hydrochloride 在 dimethyl sulfide borane 、 盐酸 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 N-hexyl-[(5R,6R)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan]-6-amine
  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

文献信息

• Design, synthesis, and structure–activity relationship of novel opioid κ-agonists
  作者：Koji Kawai、Jun Hayakawa、Toru Miyamoto、Yoshifumi Imamura、Shinichi Yamane、Hisanori Wakita、Hideaki Fujii、Kuniaki Kawamura、Hirotoshi Matsuura、Naoki Izumimoto、Ryosuke Kobayashi、Takashi Endo、Hiroshi Nagase

  DOI：10.1016/j.bmc.2008.09.011

  日期：2008.10

  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.