2-[1-(4-Methoxy-3-phenethyloxy-phenyl)-meth-(E)-ylidene]-butyric acid ethyl ester | 177587-72-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[1-(4-Methoxy-3-phenethyloxy-phenyl)-meth-(E)-ylidene]-butyric acid ethyl ester
• 英文别名: Ethyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-ethylacrylate；ethyl 2-[[4-methoxy-3-(2-phenylethoxy)phenyl]methylidene]butanoate
• CAS: 177587-72-3
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: ZKWMBRJKTNSTFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-(4-Methoxy-3-phenethyloxy-phenyl)-meth-(E)-ylidene]-butyric acid ethyl ester 在 palladium on activated charcoal 氢氧化钾 、 叠氮磷酸二苯酯 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 25.5h， 生成 1-(4-Methoxy-3-phenethyloxy-benzyl)-propylamine
  参考文献：
  名称：

  Synthesis and SAR of 1-Alkyl-2-phenylethylamine Derivatives Designed from N,N-Dipropyl-4-methoxy-3-(2-phenylethoxy)phenylethylamine To Discover σ₁ Ligands

  摘要：

  The synthesis and structure-activity relationships (SAR) of 1-alkyl-2-phenylethylamine derivatives 5-8 designed from N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl] ethylamine hydrochloride (1, NE-100) are presented. The SAR between compound 1 and 1-alkyl-2-phenylethylamine derivatives suggested that the alkyl group on the 1-position carbon of 2-[4-methoxy-3-(2-phenylethyl)phenyl]ethylamine derivatives played the role of one of the propyl groups on the aminic nitrogen of compound 1. (-)-N-Propyl-1-butyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6d, NE-537) and (-)-N-propyl-1-(3-methybutyl)2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6i, NE-535), typical compounds in this series, have potent and selective ol affinity.

  DOI：

  10.1021/jm990135j
• 作为产物：
  描述：

  2-膦酰丁酸三乙脂 、 4-甲氧基-3-苯乙氧基苯甲醛 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.5h， 生成 2-[1-(4-Methoxy-3-phenethyloxy-phenyl)-meth-(E)-ylidene]-butyric acid ethyl ester
  参考文献：
  名称：

  Synthesis and SAR of 1-Alkyl-2-phenylethylamine Derivatives Designed from N,N-Dipropyl-4-methoxy-3-(2-phenylethoxy)phenylethylamine To Discover σ₁ Ligands

  摘要：

  The synthesis and structure-activity relationships (SAR) of 1-alkyl-2-phenylethylamine derivatives 5-8 designed from N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl] ethylamine hydrochloride (1, NE-100) are presented. The SAR between compound 1 and 1-alkyl-2-phenylethylamine derivatives suggested that the alkyl group on the 1-position carbon of 2-[4-methoxy-3-(2-phenylethyl)phenyl]ethylamine derivatives played the role of one of the propyl groups on the aminic nitrogen of compound 1. (-)-N-Propyl-1-butyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6d, NE-537) and (-)-N-propyl-1-(3-methybutyl)2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6i, NE-535), typical compounds in this series, have potent and selective ol affinity.

  DOI：

  10.1021/jm990135j

文献信息

• Optically active substituted phenylalkylamine derivatives
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US05990151A1

  公开（公告）日：1999-11-23

  The present invention relates to an optically active, substituted phenylalkylamine derivative represented by Formula [1]: ##STR1## wherein A is a substituted or non-substituted phenyl or thienyl; X.sup.1 is hydrogen, halogen, hydroxyl or a substituted or non-substituted C.sub.1-5 alkoxy; R.sup.1 and R.sup.2 are equally or differently hydrogen, C.sub.1-7 alkyl, C.sub.3-7 alkenyl or C.sub.3-7 alkynyl; R.sup.3 is C.sub.1-10 alkyl, C.sub.2-10 alkenyl or C.sub.2-10 alkynyl; n is an integer from 2 to 5; and m is an integer from 1 to 4, or a pharmaceutically acceptable salt thereof, and pharmaceutical use of such compound or salt. The compound of the invention is excellent in sigma 1 receptor antagonism and useful for treating schizophrenia, depression, anxiety, cerebrovascular diseases/senile troublesome behaviors, and cognitive dysfunctions and motor dysfunctions such as Alzheimer's disease, Parkinson's disease and Huntington's disease which are neurodegenerative diseases. Further, the compound of the invention is also useful for treating dependence resulted from drug abuse.

  本发明涉及一种光学活性的取代苯基烷基胺衍生物，其由公式[1]表示：##STR1##其中，A是取代或未取代的苯基或噻吩基；X1是氢、卤素、羟基或取代或未取代的C1-5烷氧基；R1和R2是相同或不同的氢、C1-7烷基、C3-7烯基或C3-7炔基；R3是C1-10烷基、C2-10烯基或C2-10炔基；n是从2到5的整数；m是从1到4的整数，或其药学上可接受的盐，以及该化合物或盐的药物用途。该发明的化合物在sigma 1受体拮抗作用方面表现优异，适用于治疗精神分裂症、抑郁症、焦虑症、脑血管疾病/老年人的麻烦行为、认知功能障碍和运动功能障碍，如神经退行性疾病阿尔茨海默病、帕金森病和亨廷顿病。此外，该发明的化合物还适用于治疗由药物滥用引起的依赖症。