2-(3,5-dimethoxyphenyl)ethan-1-amine hydrochloride | 637-26-3

• 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: 2-(3,5-dimethoxyphenyl)ethan-1-amine hydrochloride
• 英文别名: (3,5-dimethoxyphenyl)ethylamine hydrochloride；3,5-dimethoxy-phenethylamine; hydrochloride；3,5-Dimethoxy-phenaethylamin; Hydrochlorid；2-(3,5-dimethoxyphenyl)ethanamine;hydrochloride
• CAS: 637-26-3
• 化学式: C₁₀H₁₅NO₂*ClH
• 分子量: 217.696
• InChiKey: NYEFQPLFIIYNRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethoxyphenyl)ethan-1-amine hydrochloride 在 甲酸 、 (S,S)-N-(对甲苯磺酰)-1,2-二苯乙烷二胺(对异丙基苯)氯化钌(II) 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 (S)-1,3-dimethoxy-4-hydroxymethyl-10,11-methylenedioxytetrahydroprotoberberine
  参考文献：
  名称：

  Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: Selective inhibitors of dopamine D1 receptor

  摘要：

  A series of new tetrahydroprotoberberine (THPB) derivatives were designed, synthesized, and tested for their binding affinity towards dopamine (D-1 and D-2) and serotonin (5-HT1A and 5-HT2A) receptors. Many of the THPB compounds exhibited high binding affinity and activity at the dopamine D-1 receptor, as well as high selectivity for the D-1 receptor over the D-2, 5-HT1A, and 5-HT2A receptors. Among these, compound 19c exhibited a promising D-1 receptor binding affinity (K-i = 2.53 nM) and remarkable selectivity versus D2R (inhibition = 81.87%), 5-HT1AR (inhibition = 61.70%), and 5-HT2AR (inhibition = 24.96%). Compared with l-(S)-stepholidine (l-SPD) (D-1 K-i = 6.23 nM, D-2 K-i = 56.17 nM), compound 19c showed better binding affinity for the D-1 receptor (2.5-fold higher) and excellent D-2/D-1 selectivity. Functional assays found compounds 18j, 18k, and 19c are pure D-1 receptor antagonists. These results indicate that removing the C10 hydroxy group and introducing a methoxy group at C11 of the pharmacophore of l-SPD can reverse the function of THPB compounds at the D-1 receptor. These results are in accord with molecular docking studies. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.057
• 作为产物：
  描述：

  3,5-dimethoxy-β-nitrostyrene 在 lithium aluminium tetrahydride 、 水 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 以69%的产率得到2-(3,5-dimethoxyphenyl)ethan-1-amine hydrochloride
  参考文献：
  名称：

  Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: Selective inhibitors of dopamine D1 receptor

  摘要：

  A series of new tetrahydroprotoberberine (THPB) derivatives were designed, synthesized, and tested for their binding affinity towards dopamine (D-1 and D-2) and serotonin (5-HT1A and 5-HT2A) receptors. Many of the THPB compounds exhibited high binding affinity and activity at the dopamine D-1 receptor, as well as high selectivity for the D-1 receptor over the D-2, 5-HT1A, and 5-HT2A receptors. Among these, compound 19c exhibited a promising D-1 receptor binding affinity (K-i = 2.53 nM) and remarkable selectivity versus D2R (inhibition = 81.87%), 5-HT1AR (inhibition = 61.70%), and 5-HT2AR (inhibition = 24.96%). Compared with l-(S)-stepholidine (l-SPD) (D-1 K-i = 6.23 nM, D-2 K-i = 56.17 nM), compound 19c showed better binding affinity for the D-1 receptor (2.5-fold higher) and excellent D-2/D-1 selectivity. Functional assays found compounds 18j, 18k, and 19c are pure D-1 receptor antagonists. These results indicate that removing the C10 hydroxy group and introducing a methoxy group at C11 of the pharmacophore of l-SPD can reverse the function of THPB compounds at the D-1 receptor. These results are in accord with molecular docking studies. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.057

文献信息

• Dopamine receptor model and its application in the design of a new class of rigid pyrrolo[2,3-g]isoquinoline antipsychotics
  作者：Gary L. Olson、Ho-Chuen Cheung、Keith D. Morgan、John F. Blount、Louis Todaro、Leo Berger、Arnold B. Davidson、Edward Boff

  DOI：10.1021/jm00141a002

  日期：1981.9

  antagonism) and one lipophilic auxiliary binding site are identified. The geometry is defined via the three-dimensional structures of drugs exhibiting receptor activity, including (R)-apomorphine, (+)-dexclamol, and molindone (whose crystal structure has been determined). A new conformationally rigid pyrrolo[2,3-g]isoquinoline derivative has been designed to conform to the receptor model. The compound

  描述了一种抗精神病药与多巴胺受体相互作用的假想模型。该三维分子模型是根据各种类型的抗精神病药的药效基团与假定的受体蛋白氨基酸侧链取代基之间可能存在的分子间相互作用而开发的。确定了三个基本的结合位点（可能需要拮抗作用之一）和一个亲脂性的辅助结合位点。几何形状是通过具有受体活性的药物的三维结构定义的，包括（R）-阿扑吗啡，（+）-右旋糖醇和molindone（已确定其晶体结构）。一种新的构象刚性吡咯并[2,3-g]异喹啉衍生物已被设计为符合受体模型。化合物（+/-）-1（2,6-二甲基-3-乙基-4,4a，5，6,7,8,8a，9-八氢-4a，8a-反式-1H-吡咯并[2,3-g]异喹啉-4-酮; Ro 22-1319）表现出有效的抗精神病药样活性。该活性是立体特异性的，存在于（-）对映异构体中，通过（-）-1.HCl的X射线晶体结构分析预测和证实，该活性具有4aR，8aR绝对构型。
• BERGER, L.;OLSON, G. L.
  作者：BERGER, L.、OLSON, G. L.

  DOI：——

  日期：——
• US4260762A
  申请人：——

  公开号：US4260762A

  公开（公告）日：1981-04-07
• US4349678A
  申请人：——

  公开号：US4349678A

  公开（公告）日：1982-09-14
• US4442291A
  申请人：——

  公开号：US4442291A

  公开（公告）日：1984-04-10