3-methoxy-4-(pent-4-yn-1-yloxy)benzoic acid | 1346263-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methoxy-4-(pent-4-yn-1-yloxy)benzoic acid
• 英文别名: 3-Methoxy-4-pent-4-ynoxybenzoic acid；3-methoxy-4-pent-4-ynoxybenzoic acid
• CAS: 1346263-95-3
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: AEIGSEVSWRBXSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-(pent-4-yn-1-yloxy)benzoic acid 在 copper(ll) sulfate pentahydrate 、 TATU 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-[3-[1-[8-[4-[3-[4-[[[4-[(indan-2-yl)(propyl)amino]butyl]amino]carbonyl]-2-methoxyphenoxy]propyl]-1H-1,2,3-triazol-1-yl]octyl]-1H-1,2,3-triazol-4-yl]propoxy]-3-methoxy-N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]benzamide
  参考文献：
  名称：

  Development of a Bivalent Dopamine D₂ Receptor Agonist

  摘要：

  Bivalent D-2 agonists may function as useful molecular probes for the discovery of novel neurological therapeutics. On the basis of our recently developed bivalent dopamine D-2 receptor antagonists of type 1, the bivalent agonist 2 was synthesized when a spacer built from 22 atoms was employed. Compared to the monovalent control compound 6 containing a capped spacer, the bis-aminoindane derivative 2 revealed substantial steepening of the competition curve, indicating a bivalent binding mode. Dimer-specific Hill slopes were not a result of varying functional properties because both the dopaminergic 2 and the monovalent control agent 6 proved to be D-2 agonists substantially inhibiting cAMP accumulation and inducing D-2 receptor internalization. Investigation of the heterobivalent ligands 8 and 9, containing an agonist and a phenylpiperazine-based antagonist pharmacophore, revealed moderate steepening of the displacement curves and antagonist to very weak partial agonist properties.

  DOI：

  10.1021/jm2009919
• 作为产物：
  描述：

  methyl 3-methoxy-4-(pent-4-yn-1-yloxy)benzoate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以89%的产率得到3-methoxy-4-(pent-4-yn-1-yloxy)benzoic acid
  参考文献：
  名称：

  Development of a Bivalent Dopamine D₂ Receptor Agonist

  摘要：

  Bivalent D-2 agonists may function as useful molecular probes for the discovery of novel neurological therapeutics. On the basis of our recently developed bivalent dopamine D-2 receptor antagonists of type 1, the bivalent agonist 2 was synthesized when a spacer built from 22 atoms was employed. Compared to the monovalent control compound 6 containing a capped spacer, the bis-aminoindane derivative 2 revealed substantial steepening of the competition curve, indicating a bivalent binding mode. Dimer-specific Hill slopes were not a result of varying functional properties because both the dopaminergic 2 and the monovalent control agent 6 proved to be D-2 agonists substantially inhibiting cAMP accumulation and inducing D-2 receptor internalization. Investigation of the heterobivalent ligands 8 and 9, containing an agonist and a phenylpiperazine-based antagonist pharmacophore, revealed moderate steepening of the displacement curves and antagonist to very weak partial agonist properties.

  DOI：

  10.1021/jm2009919

文献信息

• Development of a Bivalent Dopamine D₂ Receptor Agonist
  作者：Julia Kühhorn、Angela Götz、Harald Hübner、Dawn Thompson、Jennifer Whistler、Peter Gmeiner

  DOI：10.1021/jm2009919

  日期：2011.11.24

  Bivalent D-2 agonists may function as useful molecular probes for the discovery of novel neurological therapeutics. On the basis of our recently developed bivalent dopamine D-2 receptor antagonists of type 1, the bivalent agonist 2 was synthesized when a spacer built from 22 atoms was employed. Compared to the monovalent control compound 6 containing a capped spacer, the bis-aminoindane derivative 2 revealed substantial steepening of the competition curve, indicating a bivalent binding mode. Dimer-specific Hill slopes were not a result of varying functional properties because both the dopaminergic 2 and the monovalent control agent 6 proved to be D-2 agonists substantially inhibiting cAMP accumulation and inducing D-2 receptor internalization. Investigation of the heterobivalent ligands 8 and 9, containing an agonist and a phenylpiperazine-based antagonist pharmacophore, revealed moderate steepening of the displacement curves and antagonist to very weak partial agonist properties.