3-(3-Chlorophenyl)-1-methylpyrrole | 1021700-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(3-Chlorophenyl)-1-methylpyrrole
• CAS: 1021700-59-3
• 化学式: C₁₁H₁₀ClN
• 分子量: 191.66
• InChiKey: PZEXBZWRIBJAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (E)-N-(2-(3-chlorophenyl)-3-(dimethylamino)allylidene)-N-methylmethanaminium perchlorate 在 吡啶 、 sodium methylate 作用下， 反应 24.0h， 以33.6%的产率得到3-(3-Chlorophenyl)-1-methylpyrrole
  参考文献：
  名称：

  Structure–activity relationships in the inhibition of monoamine oxidase B by 1-methyl-3-phenylpyrroles

  摘要：

  Methyl-3-phenyl-3-pyrrolines are structural analogues of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and like MPTP are selective substrates of monoamine oxidase B (MAO-B). As part of an ongoing investigation into the substrate properties of various 1-methyl-3-phenyl-3-pyrrolinyl derivatives, it is shown in the present study that their respective MAO-B catalyzed oxidation products act as reversible competitive inhibitors of the enzyme. The most potent inhibitor among the oxidation products considered was 1-methyl-3-(4-trifluoromethylphenyl)pyrrole with an enzyme-inhibitor dissociation constant (K-i value) of 1.30 mu M. The least potent inhibitor was found to be 1-methyl-3-phenylpyrrole with a K-i value of 118 mu M. The results of an SAR study established that the potency of MAO-B inhibition by the 1-methyl-3-phenylpyrrolyl derivatives examined here is dependent on the Taft steric parameter (E-s) and Swain-Lupton electronic constant (F) of the substituents attached to C-4 of the phenyl ring. Electron-withdrawing substituents with a large degree of steric bulkiness appear to enhance inhibition potency. Potency was also found to vary with the substituents at C-3, again with E-s and F being the principal substituent descriptors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.059

文献信息

• Structure–activity relationships in the inhibition of monoamine oxidase B by 1-methyl-3-phenylpyrroles
  作者：Modupe O. Ogunrombi、Sarel F. Malan、Gisella Terre’Blanche、Neal Castagnoli、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bmc.2007.11.059

  日期：2008.3

  Methyl-3-phenyl-3-pyrrolines are structural analogues of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and like MPTP are selective substrates of monoamine oxidase B (MAO-B). As part of an ongoing investigation into the substrate properties of various 1-methyl-3-phenyl-3-pyrrolinyl derivatives, it is shown in the present study that their respective MAO-B catalyzed oxidation products act as reversible competitive inhibitors of the enzyme. The most potent inhibitor among the oxidation products considered was 1-methyl-3-(4-trifluoromethylphenyl)pyrrole with an enzyme-inhibitor dissociation constant (K-i value) of 1.30 mu M. The least potent inhibitor was found to be 1-methyl-3-phenylpyrrole with a K-i value of 118 mu M. The results of an SAR study established that the potency of MAO-B inhibition by the 1-methyl-3-phenylpyrrolyl derivatives examined here is dependent on the Taft steric parameter (E-s) and Swain-Lupton electronic constant (F) of the substituents attached to C-4 of the phenyl ring. Electron-withdrawing substituents with a large degree of steric bulkiness appear to enhance inhibition potency. Potency was also found to vary with the substituents at C-3, again with E-s and F being the principal substituent descriptors. (C) 2007 Elsevier Ltd. All rights reserved.