benzyl (4-((2-(((4bS,8R,8aS,14bR)-7-(cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-13-yl)amino)-2-oxoethyl)amino)-4-oxobutanoyl)glycinate | 804483-34-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: benzyl (4-((2-(((4bS,8R,8aS,14bR)-7-(cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-13-yl)amino)-2-oxoethyl)amino)-4-oxobutanoyl)glycinate
• CAS: 804483-34-9
• 化学式: C₄₁H₄₃N₅O₈
• 分子量: 733.821
• InChiKey: IZMFULDCPCSKQU-NXKNDHFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  54.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  182.32
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzyl (4-((2-(((4bS,8R,8aS,14bR)-7-(cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-13-yl)amino)-2-oxoethyl)amino)-4-oxobutanoyl)glycinate 在 氢气 作用下， 反应 48.0h， 以60%的产率得到2-[[4-[[2-[[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5(10),6,8,15,17,19(25)-heptaen-9-yl]amino]-2-oxoethyl]amino]-4-oxobutanoyl]amino]acetic acid
  参考文献：
  名称：

  A Bivalent Ligand (KDN-21) Reveals Spinal δ and κ Opioid Receptors Are Organized as Heterodimers That Give Rise to δ₁ and κ₂ Phenotypes. Selective Targeting of δ−κ Heterodimers

  摘要：

  In view of recent pharmacological studies suggesting the existence of delta-kappa opioid receptor heterodimers/oligomers in the spinal cord, we have synthesized and evaluated (intrathecally in mice) a series of bivalent ligands (KDN series) containing kappa and delta antagonist pharmacophores. Pharmacological and binding data have provided evidence for the bridging of spinal delta-kappa receptor heterodimers by KDN-21 and for their identification as delta(1) and kappa(2). The selectivity profile of KDN-21 and the apparent absence of coupled delta(1)-kappa(2) phenotypes in the brain suggest a new approach for targeting receptors.

  DOI：

  10.1021/jm0342358
• 作为产物：
  描述：

  succinyl-Gly-OBzl 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.67h， 生成 benzyl (4-((2-(((4bS,8R,8aS,14bR)-7-(cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-13-yl)amino)-2-oxoethyl)amino)-4-oxobutanoyl)glycinate
  参考文献：
  名称：

  A Bivalent Ligand (KDN-21) Reveals Spinal δ and κ Opioid Receptors Are Organized as Heterodimers That Give Rise to δ₁ and κ₂ Phenotypes. Selective Targeting of δ−κ Heterodimers

  摘要：

  In view of recent pharmacological studies suggesting the existence of delta-kappa opioid receptor heterodimers/oligomers in the spinal cord, we have synthesized and evaluated (intrathecally in mice) a series of bivalent ligands (KDN series) containing kappa and delta antagonist pharmacophores. Pharmacological and binding data have provided evidence for the bridging of spinal delta-kappa receptor heterodimers by KDN-21 and for their identification as delta(1) and kappa(2). The selectivity profile of KDN-21 and the apparent absence of coupled delta(1)-kappa(2) phenotypes in the brain suggest a new approach for targeting receptors.

  DOI：

  10.1021/jm0342358