1-(3-氯-2-甲基苯基)哌嗪 | 54711-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(3-氯-2-甲基苯基)哌嗪
• 英文名称: 1-(3-chloro-2-methylphenyl)piperazine
• 英文别名: 4-(3-chloro-2-methylphenyl)piperazine
• CAS: 54711-70-5
• 化学式: C₁₁H₁₅ClN₂
• 分子量: 210.706
• InChiKey: XSWFFTOMNHATMS-UHFFFAOYSA-N

物化性质

• 沸点：
  121-124 °C(Press: 1 Torr)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde 、 1-(3-氯-2-甲基苯基)哌嗪 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 7-{4-[4-(3-chloro-2-methyl-phenyl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one
  参考文献：
  名称：

  Discovery of PF-00217830: Aryl piperazine napthyridinones as D2 partial agonists for schizophrenia and bipolar disorder

  摘要：

  The synthesis and structure-activity relationship (SAR) of a novel series of aryl piperazine napthyridinone D-2 partial agonists is described. Our goal was to optimize the affinities for the D-2, 5-HT2A and 5-HT1A receptors, such that the D-2/5-HT2A ratio was greater than 5 to ensure maximal occupancy of these receptors when the D-2 occupancy reached efficacious levels. This strategy led to identification of PF-00217830 (2) with robust inhibition of sLMA (MED = 0.3 mg/kg) and DOI-induced head twitches in rats (31% and 78% at 0.3 and 1 mg/kg) with no catalepsy observed at the highest dose tested (10 mg/kg). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.059
• 作为产物：
  描述：

  二(2-氯乙基)胺盐酸盐 、 3-氯-2-甲基苯胺 在 sodium carbonate 作用下， 以 正丁醇 为溶剂， 反应 48.5h， 以81%的产率得到1-(3-氯-2-甲基苯基)哌嗪
  参考文献：
  名称：

  ARYLPIPERAZINE-CONTAINING PURINE DERIVATIVES AND USES THEREOF

  摘要：

  一种含有芳基哌嗪的嘌呤衍生物以及包含其作为活性成分的药物组合物被提供，用于预防或治疗抑郁症。

  公开号：

  US20120232090A1

文献信息

• Development of Thieno[3`,2`:5,6]thiopyrano[4,3-c]pyrazole-3-carboxamide Derivatives as the Estrogen Receptor Ligands: Synthesis, Characterization and Biological Activity
  作者：Xin Wang、Rui Sun、Yushu Huang、Yisi Yan、Miaomiao Gao、Dan-Ni Wang、Diwa Koirala、Da-Wei Li、Chun Hu

  DOI：10.2174/1573406410666140428145753

  日期：2014.10.23

  Estrogen receptors (ERs) are members of a superfamily of ligand-modulated nuclear receptors, which have been associated with an increased risk of cardiovascular diseases and breast cancer. Based on molecular docking studies, 1,4-dihydrothieno[3’,2’:5,6]thiopyrano[4,3-c]pyrazole-3-carboxamide derivatives as estrogen receptor inhibitors with a new scaffold , have been synthesized and tested for the antitumor activity on the ER expressing (ER dependent) human MCF-7 breast cancer cell line. According to the biological activity evaluation, compound 6a demonstrated the most potent antiproliferative activity (relative inhibitory rate: 100%). Several of these compounds exhibited moderate antitumor activity and worthy of further modification to obtain more potent anticancer candidate drugs.

  雌激素受体（ERs）属于配体调节核受体超级家族，与心血管疾病和乳腺癌风险增加有关。基于分子对接研究，我们合成并测试了具有新型骨架的1,4-二氢噻吩并[3’,2’:5,6]噻吔并[4,3-c]吡唑-3-羧酰胺衍生物作为雌激素受体抑制剂，对表达ER的人类MCF-7乳腺癌细胞株的抗肿瘤活性。生物活性评估显示，化合物6a表现出最强的抗增殖活性（相对抑制率：100%）。多个化合物显示出中等抗肿瘤活性，值得进一步改造以获得更强的候选抗癌药物。
• [EN] 5-[(PIPERAZIN-1-YL)-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AS ADAMTS INHIBITORS FOR THE TREATMENT OF OSTEOARTHRITIS<br/>[FR] DÉRIVÉS 5-[(PIPÉRAZINE-1-YL) -3-OXO-PROPYL]-IMIDAZOLIDINE -2,4-DIONE COMME INHIBITEURS D'ADAMTS POUR LE TRAITEMENT DE L'ARTHROSE
  申请人：GALAPAGOS NV

  公开号：WO2016102347A1

  公开（公告）日：2016-06-30

  The present invention discloses compounds according to Formula (I), wherein R, R2, R3a, R3b, and Cy are as defined herein. The present invention discloses compounds inhibiting ADAMTS, methods for their production, pharmaceutical compositions comprising the same and methods for the prophylaxis and/or treatment of inflammatory conditions and/or diseases involving degradation of cartilage and/or disruption of cartilage homeostasis.

  本发明公开了根据式(I)的化合物，其中R、R2、R3a、R3b和Cy如本文所定义。本发明公开了抑制ADAMTS的化合物、其制备方法、包含该化合物的药物组合物以及用于预防和/或治疗涉及软骨降解和/或软骨稳态破坏的炎症状况和/或疾病的方法。
• [EN] NOVEL SUBSTITUTED PIPERAZINE AMIDE COMPOUNDS AS INDOLEAMINE 2, 3-DIOXYGENASE (IDO) INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS DE PIPERAZINE AMIDE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE L'INDOLÉAMINE 2,3-DIOXYGÉNASE (IDO)
  申请人：MERCK SHARP & DOHME

  公开号：WO2020112581A1

  公开（公告）日：2020-06-04

  Disclosed herein are compounds of formula (I) which are inhibitors of an IDO enzyme: (I). Also disclosed herein are uses of the compounds in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising these compounds. Further disclosed herein are uses of the compositions in the potential treatment or prevention of an IDO-associated disease or disorder.

  本文披露了一种化合物，其化学式为（I），可以作为IDO酶的抑制剂：（I）。本文还披露了这些化合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。本文还披露了包含这些化合物的组合物。此外，本文还披露了这些组合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。
• Studies on 2(1H)-quinolinone derivatives as neuroleptic agents. I. Synthesis and biological activities of (4-phenyl-1-piperazinyl)-propoxy-2(1H)-quinolinone derivatives.
  作者：KAZUO BANNO、TAKAFUMI FUJIOKA、TETSURO KIKUCHI、YASUO OSHIRO、TAKASHI HIYAMA、KAZUYUKI NAKAGAWA

  DOI：10.1248/cpb.36.4377

  日期：——

  With the aim of developing a novel neuroleptic drug, a series of ω-(4-phenyl-1-piperazinyl)-alkoxy-2 (1H)-quinolinone derivatives have been synthesized and tested for anti-methamphetamine and anti-epinephrine activities. Most of the derivatives were found to possess a potent antimethamphetamine activity in the jumping behavior test on mice treated with 3-(3, 4-dihydroxyphenyl)-L-alanine (L-DOPA) and methamphetamine, or in the lethality test with methamphetamine-treated mice. They also showed relatively high anti-epinephrine potency depending on the nature or number of substituents on the phenyl group in the 4-phenyl-1-piperazinyl moiety; some of these compounds induced only weak catalepsy in mice. Among them, 7-3-[4-(2, 3-dimethylphenyl)-1-piperazinyl]propoxy}-2 (1H)-quinolinone (OPC-4392), which was suggested to be a dopamine autoreceptor agonist, was selected for further investigations. The structure-activity relationships are also discussed.

  为了开发一种新型的神经安定药物，合成了一系列ω-(4-苯基-1-哌嗪基)-烷氧基-2(1H)-喹啉酮衍生物，并测试了它们的抗甲基苯丙胺和抗肾上腺素活性。大多数衍生物在3-(3, 4-二羟基苯基)-L-天冬氨酸（L-DOPA）和甲基苯丙胺处理的小鼠的跳跃行为测试中显示出强效的抗甲基苯丙胺活性，或者在甲基苯丙胺处理的小鼠的致死性测试中表现出显著效果。它们还表现出相对较高的抗肾上腺素效能，这取决于取代基在4-苯基-1-哌嗪基上的性质或数量；其中一些化合物在小鼠中仅引起轻微的强直症。在这些化合物中，7-3-[4-(2, 3-二甲基苯基)-1-哌嗪基]丙氧基}-2(1H)-喹啉酮（OPC-4392），被认为是一种多巴胺自受体激动剂，已被选定用于进一步研究。同时，本文也讨论了结构-活性关系。
• Piperazine derivatives
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US05681954A1

  公开（公告）日：1997-10-28

  A compound represented by formula (I): ##STR1## wherein Q represents an aryl group, a heterocyclic group, a diarylmethyl group, an aralkyl group composed of an aryl group and an alkylene group, an alkyl group or a cycloalkyl group, in which the aryl group, heterocyclic group, and the aryl moiety of the diarylmethyl group and aralkyl group may be substituted with one or more substituents; R represents a bicyclic, substituted, nitrogen-containing heterocyclic group or a substituted phenyl group, in which the nitrogen-containing heterocyclic group is composed of a 5-membered, substituted, aromatic or saturated ring containing one or two nitrogen atoms and a 6-membered ring; and Z represents an alkylene group, an alkenylene group, an alkylene group, a carbonyl group, an alkylene group containing a carbonyl group or an oxalyl group, or a salt thereof. The compound has calmodulin inhibitory activity and is useful as a treating agent for diseases in the circulatory organs or in the cerebral region which are caused by excessive activation of calmodulin.

  一种由化学式(I)表示的化合物：##STR1## 其中Q代表芳基、杂环基、二芳基甲基基、芳基和烷基组成的芳基烷基基团、烷基或环烷基，其中芳基、杂环基、二芳基甲基基和芳基烷基基团中的芳基可被一个或多个取代基取代；R代表双环取代的含氮杂环基或取代的苯基，其中含氮杂环基由一个含有一个或两个氮原子的5元取代芳香或饱和环和一个6元环组成；Z代表烷基、烯烃基、烷基、羰基、含有羰基的烷基或草酸基，或其盐。该化合物具有钙调蛋白抑制活性，并可用作治疗因钙调蛋白过度活化引起的循环器官或脑区疾病的治疗剂。