1-Chloro-3-[chloro-(4-fluorophenyl)methyl]benzene | 247089-79-8

• 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: 1-Chloro-3-[chloro-(4-fluorophenyl)methyl]benzene
• CAS: 247089-79-8
• 化学式: C₁₃H₉Cl₂F
• 分子量: 255.119
• InChiKey: ZCZNIOBFCPSMHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-tropanol 、 1-Chloro-3-[chloro-(4-fluorophenyl)methyl]benzene 生成
  参考文献：
  名称：

  CoMFA Study of Novel Phenyl Ring-Substituted 3α-(Diphenylmethoxy)tropane Analogues at the Dopamine Transporter

  摘要：

  A series of phenyl ring-substituted analogues of 3 alpha-(diphenylmethoxy)tropane (benztropine) has been prepared as novel probes for the dopamine transporter. Cross-validated comparative molecular field analysis (CoMFA) models of the binding domain on the dopamine transporter were constructed using 37 geometry-optimized structures of these compounds and their corresponding binding affinities (Ki values) for the displacement of [H-3]WIN 35,428 or potency of [H-3]dopamine uptake inhibition (IC50 values) in rat caudate putamen tissue. The most predictive model (q(2) = 0.78) correlated the steric component of CoMFA to the dependent variable of [H-3]WIN 35,428 binding affinities. A novel series of seven phenyl ring-substituted analogues of 3a-(diphenylmethoxy)tropane was prepared, and our best molecular model was used to accurately predict their binding affinities. This study is the first to provide a CoMFA model for this class of dopamine uptake inhibitors. This model represents an advancement in the design of novel dopamine transporter ligands, based on 3a-(diphenylmethoxy)tropane, and further substantiates structure-activity relationships that have previously been proposed for this class of compounds. This CoMFA model can now be used to predict the binding affinities of novel 3a-(diphenylmethoxy)tropane analogues at the dopamine transporter and will be useful in the design of molecular probes within this class of dopamine uptake inhibitors.

  DOI：

  10.1021/jm980701v
• 作为产物：
  描述：

  (4-fluorophenyl)(3-chlorophenyl)methanol 在 氯化亚砜 作用下， 生成 1-Chloro-3-[chloro-(4-fluorophenyl)methyl]benzene
  参考文献：
  名称：

  CoMFA Study of Novel Phenyl Ring-Substituted 3α-(Diphenylmethoxy)tropane Analogues at the Dopamine Transporter

  摘要：

  A series of phenyl ring-substituted analogues of 3 alpha-(diphenylmethoxy)tropane (benztropine) has been prepared as novel probes for the dopamine transporter. Cross-validated comparative molecular field analysis (CoMFA) models of the binding domain on the dopamine transporter were constructed using 37 geometry-optimized structures of these compounds and their corresponding binding affinities (Ki values) for the displacement of [H-3]WIN 35,428 or potency of [H-3]dopamine uptake inhibition (IC50 values) in rat caudate putamen tissue. The most predictive model (q(2) = 0.78) correlated the steric component of CoMFA to the dependent variable of [H-3]WIN 35,428 binding affinities. A novel series of seven phenyl ring-substituted analogues of 3a-(diphenylmethoxy)tropane was prepared, and our best molecular model was used to accurately predict their binding affinities. This study is the first to provide a CoMFA model for this class of dopamine uptake inhibitors. This model represents an advancement in the design of novel dopamine transporter ligands, based on 3a-(diphenylmethoxy)tropane, and further substantiates structure-activity relationships that have previously been proposed for this class of compounds. This CoMFA model can now be used to predict the binding affinities of novel 3a-(diphenylmethoxy)tropane analogues at the dopamine transporter and will be useful in the design of molecular probes within this class of dopamine uptake inhibitors.

  DOI：

  10.1021/jm980701v

文献信息

• CoMFA Study of Novel Phenyl Ring-Substituted 3α-(Diphenylmethoxy)tropane Analogues at the Dopamine Transporter
  作者：Amy Hauck Newman、Sari Izenwasser、Michael J. Robarge、Richard H. Kline

  DOI：10.1021/jm980701v

  日期：1999.9.1

  A series of phenyl ring-substituted analogues of 3 alpha-(diphenylmethoxy)tropane (benztropine) has been prepared as novel probes for the dopamine transporter. Cross-validated comparative molecular field analysis (CoMFA) models of the binding domain on the dopamine transporter were constructed using 37 geometry-optimized structures of these compounds and their corresponding binding affinities (Ki values) for the displacement of [H-3]WIN 35,428 or potency of [H-3]dopamine uptake inhibition (IC50 values) in rat caudate putamen tissue. The most predictive model (q(2) = 0.78) correlated the steric component of CoMFA to the dependent variable of [H-3]WIN 35,428 binding affinities. A novel series of seven phenyl ring-substituted analogues of 3a-(diphenylmethoxy)tropane was prepared, and our best molecular model was used to accurately predict their binding affinities. This study is the first to provide a CoMFA model for this class of dopamine uptake inhibitors. This model represents an advancement in the design of novel dopamine transporter ligands, based on 3a-(diphenylmethoxy)tropane, and further substantiates structure-activity relationships that have previously been proposed for this class of compounds. This CoMFA model can now be used to predict the binding affinities of novel 3a-(diphenylmethoxy)tropane analogues at the dopamine transporter and will be useful in the design of molecular probes within this class of dopamine uptake inhibitors.