N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6,7,7a octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-N-methylcinnamamide hydrochloride | 152658-57-6

• 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-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6,7,7a octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-N-methylcinnamamide hydrochloride
• 英文别名: (2E)-N-[(5R,6R)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-3-phenyl-N-methylprop-2-enamide hydrochloride；(E)-N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-N-methyl-3-phenylprop-2-enamide;hydrochloride
• CAS: 152658-57-6
• 化学式: C₃₀H₃₄N₂O₄*ClH
• 分子量: 523.072
• InChiKey: BAFHTKCGWYXPMX-MFZMKTNQSA-N

物化性质

• 熔点：
  225 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 、 6β-N-methylnaltrexamine 以46%的产率得到N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6,7,7a octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-N-methylcinnamamide hydrochloride
  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