N-{([(3-{(S)-α-[N-{2-(3,4-dichlorophenyl)acetyl}-N'-methylamino]-α-[pyrrolidin-1-ylmethyl]methyl}phenylaminocarbonyl)methyl]aminocarbonyl)methyl}-N'-({[(naltrindol-7'-ylaminocarbonyl)methyl]aminocarbonyl}methyl)succinamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-{([(3-{(S)-α-[N-{2-(3,4-dichlorophenyl)acetyl}-N'-methylamino]-α-[pyrrolidin-1-ylmethyl]methyl}phenylaminocarbonyl)methyl]aminocarbonyl)methyl}-N'-({[(naltrindol-7'-ylaminocarbonyl)methyl]aminocarbonyl}methyl)succinamide
• 英文别名: N'-[2-[[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]-2-oxoethyl]-N-[2-[[2-[3-[(1S)-1-[[2-(3,4-dichlorophenyl)acetyl]-methylamino]-2-pyrrolidin-1-ylethyl]anilino]-2-oxoethyl]amino]-2-oxoethyl]butanediamide
• 化学式: C₅₉H₆₆Cl₂N₁₀O₁₀
• 分子量: 1146.14
• InChiKey: IHXYEGBSVZDVIN-NYSGUXNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  81
• 可旋转键数：
  21
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  267
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  、 N-((S)-1-{3-[2-(2-Amino-acetylamino)-acetylamino]-phenyl}-2-pyrrolidin-1-yl-ethyl)-2-(3,4-dichloro-phenyl)-N-methyl-acetamide 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 以69%的产率得到N-{([(3-{(S)-α-[N-{2-(3,4-dichlorophenyl)acetyl}-N'-methylamino]-α-[pyrrolidin-1-ylmethyl]methyl}phenylaminocarbonyl)methyl]aminocarbonyl)methyl}-N'-({[(naltrindol-7'-ylaminocarbonyl)methyl]aminocarbonyl}methyl)succinamide
  参考文献：
  名称：

  A Bivalent Ligand (KDAN-18) Containing δ-Antagonist and κ-Agonist Pharmacophores Bridges δ₂ and κ₁ Opioid Receptor Phenotypes

  摘要：

  To characterize delta- and kappa-opioid receptor phenotypes, bivalent ligands (KDAN series) containing delta-antagonist (naltrindole) and kappa(1)-agonist (ICI-199,441) pharmacophores were synthesized and evaluated by the intrathecal route using the mouse tail-flick assay and binding studies. The data have suggested that KDAN-18 (2) bridges phenotypic delta(2)- and kappa(1)-receptors. A conceptual model is presented to explain the organizational differences between the opioid receptors that give rise to the phenotypes (delta(1), delta(2), kappa(1), kappa(2)).

  DOI：

  10.1021/jm034234f

文献信息

• A Bivalent Ligand (KDAN-18) Containing δ-Antagonist and κ-Agonist Pharmacophores Bridges δ₂ and κ₁ Opioid Receptor Phenotypes
  作者：David J. Daniels、Amol Kulkarni、Zhihua Xie、Rashmi G. Bhushan、Philip S. Portoghese

  DOI：10.1021/jm034234f

  日期：2005.3.1

  To characterize delta- and kappa-opioid receptor phenotypes, bivalent ligands (KDAN series) containing delta-antagonist (naltrindole) and kappa(1)-agonist (ICI-199,441) pharmacophores were synthesized and evaluated by the intrathecal route using the mouse tail-flick assay and binding studies. The data have suggested that KDAN-18 (2) bridges phenotypic delta(2)- and kappa(1)-receptors. A conceptual model is presented to explain the organizational differences between the opioid receptors that give rise to the phenotypes (delta(1), delta(2), kappa(1), kappa(2)).