1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine | 43091-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine
• 英文别名: 1-(2-methoxyphenyl)-4-(2-chloroethyl)-piperazine；2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl chloride
• CAS: 43091-72-1
• 化学式: C₁₃H₁₉ClN₂O
• mdl: MFCD09753649
• 分子量: 254.76
• InChiKey: MUSOMUXTQGJZKD-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  374.0±42.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(2-Methoxyphenyl)-4-<2-(methylamino)ethyl>piperazine
  参考文献：
  名称：

  Perrone; Berardi; Leopoldo, Il Farmaco, 1995, vol. 50, # 7-8, p. 505 - 510

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(氯乙酰基)-4-(2-甲氧基苯基)哌嗪盐酸盐 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以73%的产率得到1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine
  参考文献：
  名称：

  2-[(3-Methoxyphenylethyl)phenoxy]-Based ABCB1 Inhibitors: Effect of Different Basic Side-Chains on Their Biological Properties

  摘要：

  Recently, 2-[(3-methoxyphenylethyl)phenoxy]-moiety has been selected for the design and synthesis of new small ABCB1 inhibitors. In the present paper, this moiety has been linked through a spacer of 2-5 carbon atoms to the nitrogen of three different basic nuclei such as: (i) N-4-arylpiperazine, (ii) N-4-methylpiperazine, and (iii) 6,7-dimethoxytctrahydroisoquinoline. The results demonstrated that all the selected basic nuclei were well tolerated and that, globally, the best inhibitory activity for each series was obtained when the spacer between the 2-[(3-methoxyphenylethyl)phenoxy]moiety and the basic nucleus consisted of a four-carbon chain. Among the synthesized compounds, N-4-methylpiperazine- 10C (IC50 = 0.15 W) and tetrahydroisoquinoline-derivatives 11c (IC50 = 0.08 W) with the spacer n = 4 for both series, displayed the best potency to inhibit ABCB1 activity. Moreover, for each compound, the ABCB1 interacting mechanism has been evaluated by three combined biological assays. N-4-methylpiperazine- (10a-d) and tetrahydroisoquinoline-(11a-d) derivatives were Cyclosporin A-like ABCB1 nontransported substrates.

  DOI：

  10.1021/jm800928j

文献信息

• 1-(N-phenylalkylaminoalkyl)piperazine derivatives substituted at position 2 of the phenyl ring
  申请人：Recordati S.A., Chemical and Pharmaceutical Comoany

  公开号：US20020193383A1

  公开（公告）日：2002-12-19

  The present invention is directed to novel 1-(N-phenylaminoalkyl)piperazine derivatives substituted at the position 2 of the phenyl ring. Pharmaceutical compositions comprising the compounds of the invention also are contemplated. The compounds of the present invention also are contemplated for use in treating neuromuscular dysfunction of the lower urinary tract in a mammal.

  本发明涉及在苯环的位置2被取代的新型1-(N-苯基氨基烷基)哌嗪衍生物。还考虑包括本发明化合物的药物组合物。本发明化合物还被考虑用于治疗哺乳动物下尿路神经肌肉功能障碍。
• 1-(N-phenylaminoalkyl)piperazine derivatives substituted at position 2 of the phenyl ring
  申请人：Recordati S.A. Chemical and Pharmaceutical Company

  公开号：US06399614B1

  公开（公告）日：2002-06-04

  The present invention is directed to novel 1-(N-phenylaminoalkyl)piperazine derivatives substituted at the position 2 of the phenyl ring. Pharmaceutical compositions comprising the compounds of the invention also are contemplated. The compounds of the present invention also are contemplated for use in treating neuromuscular dysfunction of the lower urinary tract in a mammal.

  本发明涉及在苯环的位置2处取代的新型1-(N-苯基氨基烷基)哌嗪衍生物。还考虑包括本发明化合物的药物组合物。本发明化合物还被考虑用于治疗哺乳动物下尿路神经肌肉功能障碍。
• Design, synthesis, and biological evaluation of arylpiperazine–benzylpiperidines with dual serotonin and norepinephrine reuptake inhibitory activities
  作者：Suresh Paudel、Srijan Acharya、Kyeong-Man Kim、Seung Hoon Cheon

  DOI：10.1016/j.bmc.2016.03.044

  日期：2016.5

  The limitations of established serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) reuptake inhibitors necessitate the development of safer and more effective therapeutic agents. Based on the structures of 4-benzylpiperidine carboxamides and trazodone, arylpiperazine–benzylpiperidines with chemical scaffolds different from those of marketed drugs were designed, synthesized, and evaluated

  既定的5-羟色胺（5-羟色胺，5-HT）和去甲肾上腺素（NE）再摄取抑制剂的局限性需要开发更安全，更有效的治疗剂。根据4-苄基哌啶羧酰胺和曲唑酮的结构，设计，合成和评估化学支架与市售药物不同的芳基哌嗪-苄基哌啶，并评估其对神经递质再摄取的抑制活性。大多数合成化合物显示出比5-HT再摄取抑制更大的NE。其活性甚至大于标准药物盐酸文拉法辛。具有三碳连接基的衍生物表现出比具有二碳连接基的衍生物更好的活性。在新合成的化合物中，第2d表现出最强的神经递质再摄取抑制作用（ NE的IC 50 = 0.38μM，5-HT的IC 50 = 1.18μM）。生物学活性数据表明，芳基哌嗪-苄基哌啶具有开发作为治疗神经精神病和神经退行性疾病的新型治疗剂的潜力。
• ADENOSINE A2A RECEPTOR ANTAGONISTS
  申请人：Moorman Allan R.

  公开号：US20080242672A1

  公开（公告）日：2008-10-02

  The present invention provides compounds of the formula wherein R 1 and R 2 have meaning as defined herein in the specification. The compounds of formula (I) are adenosine A 2A receptor antagonists and, thus, may be employed for the treatment of conditions and diseases mediated by the adenosine A 2A receptor activity. Such conditions include, but are not limited to, diseases of the central nervous system such as depression, cognitive function diseases and neurodegenerative diseases such as Parkinson's disease, senile dementia as in Alzheimer's disease or psychoses and stroke. The compounds of the present invention may also be employed for the treatment of attention related disorders such as attention deficit disorder (ADD) and attention deficit hyperactivity disorder (ADHD), extra pyramidal syndrome, e.g., dystonia, akathisia, pseudoparkinsonism and tardive dyskinesia, and disorders of abnormal movement such as restless leg syndrome (RLS) and periodic limb movement in sleep (PLMS); cirrhosis, and fibrosis and fatty liver; dermal fibrosis in diseases such as scleroderma; and the mitigation of addictive behavior. In particular, the compounds of the present invention may be employed to improve motor-impairment due to neurodegenerative diseases such as Parkinson's disease.

  本发明提供了以下式的化合物 其中R 1 和R 2 的含义如规范中所定义。式(I)的化合物是腺苷A 2A 受体拮抗剂，因此可用于治疗由腺苷A 2A 受体活性介导的疾病和病症。这些疾病包括但不限于中枢神经系统疾病，如抑郁症、认知功能疾病和神经退行性疾病，如帕金森病、老年性痴呆症、精神病和中风。本发明的化合物还可用于治疗注意力相关障碍，如注意力缺陷障碍（ADD）和注意力缺陷多动障碍（ADHD），额外锥体综合征，例如肌张力障碍、不安坐立、假性帕金森症和迟发性运动障碍，以及异常运动障碍，如不宁腿综合征（RLS）和睡眠中期肢体运动（PLMS）；肝硬化、纤维化和脂肪肝；在硬皮病等疾病中的皮肤纤维化；以及对成瘾行为的缓解。特别是，本发明的化合物可用于改善由帕金森病等神经退行性疾病引起的运动障碍。
• Benzimidazole derivatives
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US04886803A1

  公开（公告）日：1989-12-12

  Compounds are described of formula (I) ##STR1## wherein R.sup.1 is a hydrogen atom, an alkyl group, an alkoxy group, a dialkylamino group or a halogen atom; n is 1 to 4; R.sup.2 is a hydrogen atom, an alkyl group, an unsubstituted or substituted aminoalkyl group, an acyl group, an unsubstituted or substituted aralkyl group, a carboxyalkyl group, an alkoxycarbonyalkyl group or ##STR2## wherein X is an unsubstituted or substituted-phenyl, -benzyl, -benzoyl or -furoyl group; A is -NR.sup.3 - where R.sup.3 is hydrogen or alkyl, an alkylene or an alkylidene; and B is a heterocyclic group selected from triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, benzimidazolyl, benzothiazolyl, quinolyl and isoquinolyl, said heterocyclic group being optionally substituted by one or more alkyl, alkoxy, nitro or phenyl group, and the physiologically acceptable acid addition salts thereof. The compound of formula (I) are or cardiotonic activity and thus may be useful for the treatment of circulatory diseases.

  化合物具有式(I)的结构 ##STR1## 其中R1是一个氢原子、一个烷基、一个烷氧基、一个二烷基氨基或一个卤素原子；n是1到4；R2是一个氢原子、一个烷基、一个未取代或取代的氨基烷基、一个酰基、一个未取代或取代的芳烷基、一个羧基烷基、一个烷氧羰基烷基或 ##STR2## 其中X是一个未取代或取代的苯基、苄基、苯甲酰基或呋喃酰基；A是-NR3-，其中R3是氢或烷基、一个亚烷基或一个次烷基；B是一个杂环基团，选自三唑基、吡啶基、吡啶嗪基、嘧啶基、吡嗪基、苯并咪唑基、苯并噻唑基、喹啉基和异喹啉基，该杂环基团可选择性地被一个或多个烷基、烷氧基、硝基或苯基取代，以及它们的生理上可接受的酸加成盐。式(I)的化合物具有强心活性，因此可能对治疗循环系统疾病有用。