3-(3,4-dichlorophenyl)-3-(3-methoxyphenyl)propionic acid | 321525-41-1

• 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-(3,4-dichlorophenyl)-3-(3-methoxyphenyl)propionic acid
• 英文别名: 3-(3,4-Dichlorophenyl)-3-(3-methoxyphenyl)propanoic acid
• CAS: 321525-41-1
• 化学式: C₁₆H₁₄Cl₂O₃
• 分子量: 325.191
• InChiKey: AKVIQVRJXAMPJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenyl)-3-(3-methoxyphenyl)propionic acid 在 5percent Pd/C sodium tetrahydroborate 、 PPA 、 叠氮磷酸二苯酯 、 氢气 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、241.32 kPa 条件下， 反应 4.0h， 生成 trans-[3-(3,4-dichlorophenyl)-7-methoxyindan-1-yl]methylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, Synthesis, and Monoamine Transporter Binding Site Affinities of Methoxy Derivatives of Indatraline

  摘要：

  A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline affected its affinity and selectivity greatly. Except for the 4-methoxy derivative 13a,which had the same high affinity at the dopamine transporter binding site as indatraline, the other methoxy-containing analogues (13b-f and 17) exhibited lower affinity than indatraline for the three transporter binding sites. However, some of the analogues were more selective than indatraline, and the B-methoxy derivative 13c displayed the highest affinity for both the serotonin and norepinephrine transporters. This compound retained reasonable affinity for the dopamine transporter and is a promising template for the development of a long-acting inhibitor of monoamine transporters. Such inhibitors have potential as medications for treatment, as a substitution medication, or for prevention of the abuse of methamphetamine-like stimulants.

  DOI：

  10.1021/jm000329v
• 作为产物：
  描述：

  ethyl 2-cyano-3-(3-methoxyphenyl)acrylate 在 硫酸 、 碘 、 magnesium 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 29.0h， 生成 3-(3,4-dichlorophenyl)-3-(3-methoxyphenyl)propionic acid
  参考文献：
  名称：

  Design, Synthesis, and Monoamine Transporter Binding Site Affinities of Methoxy Derivatives of Indatraline

  摘要：

  A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline affected its affinity and selectivity greatly. Except for the 4-methoxy derivative 13a,which had the same high affinity at the dopamine transporter binding site as indatraline, the other methoxy-containing analogues (13b-f and 17) exhibited lower affinity than indatraline for the three transporter binding sites. However, some of the analogues were more selective than indatraline, and the B-methoxy derivative 13c displayed the highest affinity for both the serotonin and norepinephrine transporters. This compound retained reasonable affinity for the dopamine transporter and is a promising template for the development of a long-acting inhibitor of monoamine transporters. Such inhibitors have potential as medications for treatment, as a substitution medication, or for prevention of the abuse of methamphetamine-like stimulants.

  DOI：

  10.1021/jm000329v

文献信息

• Design, Synthesis, and Monoamine Transporter Binding Site Affinities of Methoxy Derivatives of Indatraline
  作者：Xiao-Hui Gu、Han Yu、Arthur E. Jacobson、Richard B. Rothman、Christina M. Dersch、Clifford George、Judith L. Flippen-Anderson、Kenner C. Rice

  DOI：10.1021/jm000329v

  日期：2000.12.1

  A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline affected its affinity and selectivity greatly. Except for the 4-methoxy derivative 13a,which had the same high affinity at the dopamine transporter binding site as indatraline, the other methoxy-containing analogues (13b-f and 17) exhibited lower affinity than indatraline for the three transporter binding sites. However, some of the analogues were more selective than indatraline, and the B-methoxy derivative 13c displayed the highest affinity for both the serotonin and norepinephrine transporters. This compound retained reasonable affinity for the dopamine transporter and is a promising template for the development of a long-acting inhibitor of monoamine transporters. Such inhibitors have potential as medications for treatment, as a substitution medication, or for prevention of the abuse of methamphetamine-like stimulants.