(S)-ethyl 5-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-5-oxopentanoate | 1403822-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-ethyl 5-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-5-oxopentanoate
• CAS: 1403822-88-7
• 化学式: C₂₁H₃₁NO₄
• 分子量: 361.481
• InChiKey: XYFVRDCNHDFQPA-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 5-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-5-oxopentanoate 在 lithium aluminium tetrahydride 、 三溴化硼 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (6S,6'S)-6,6'-(pentane-1,5-diyl-bis(propylazanediyl))-bis(5,6,7,8-tetrahydronaphthalen-1-ol)
  参考文献：
  名称：

  Novel Bivalent Ligands for D2/D3 Dopamine Receptors: Significant Cooperative Gain in D2 Affinity and Potency

  摘要：

  This report describes development of a series of novel bivalent molecules with a pharmacophore derived from the D2/D3 agonist 5-OH-DPAT. The spacer length in the bivalent compounds had a pronounced influence on affinity for D2 receptors. A 23-fold increase of D2 affinity was observed at a spacer length of 9 or 10 (compounds lid and 14b) as compared to monovalent 5-OH-DPAT (K-ij 2.5 and 2.0 vs 59 nM for 11d and 146 vs 5-OH-DPAT, respectively). The functional potency of 11d and 14b indicated a 24- and 94-fold increase in potency at the D2 receptor as compared to 5-OH-DPAT (EC50; 1.7 and 0.44 vs 41 nM for 11d and 14b vs 5-OH-DPAT, respectively). These are the most potent bivalent agonists for the D2 receptor known to date. This synergism is consonant with cooperative interaction at the two orthosteric binding sites in the homodimeric receptor.

  DOI：

  10.1021/ml3002117
• 作为产物：
  描述：

  戊二酸单乙酯酰氯 、 (S)-5-甲氧基-1,2,3,4-四氢-N-丙基-2-萘胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到(S)-ethyl 5-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-5-oxopentanoate
  参考文献：
  名称：

  Novel Bivalent Ligands for D2/D3 Dopamine Receptors: Significant Cooperative Gain in D2 Affinity and Potency

  摘要：

  This report describes development of a series of novel bivalent molecules with a pharmacophore derived from the D2/D3 agonist 5-OH-DPAT. The spacer length in the bivalent compounds had a pronounced influence on affinity for D2 receptors. A 23-fold increase of D2 affinity was observed at a spacer length of 9 or 10 (compounds lid and 14b) as compared to monovalent 5-OH-DPAT (K-ij 2.5 and 2.0 vs 59 nM for 11d and 146 vs 5-OH-DPAT, respectively). The functional potency of 11d and 14b indicated a 24- and 94-fold increase in potency at the D2 receptor as compared to 5-OH-DPAT (EC50; 1.7 and 0.44 vs 41 nM for 11d and 14b vs 5-OH-DPAT, respectively). These are the most potent bivalent agonists for the D2 receptor known to date. This synergism is consonant with cooperative interaction at the two orthosteric binding sites in the homodimeric receptor.

  DOI：

  10.1021/ml3002117