trans-2-(4-chlorophenyl)cyclopropylamine hydrochloride | 26568-25-2

• 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: trans-2-(4-chlorophenyl)cyclopropylamine hydrochloride
• 英文别名: racemic (1R,2S)-2-(4-chlorophenyl)cyclopropan-1-amine hydrochloride；Trans-2-(4-chlorophenyl)cyclopropanamine hydrochloride；(1R,2S)-2-(4-chlorophenyl)cyclopropan-1-amine;hydrochloride
• CAS: 26568-25-2
• 化学式: C₉H₁₀ClN*ClH
• mdl: MFCD28145424
• 分子量: 204.099
• InChiKey: PARPLJNCMHCNAA-OULXEKPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-2-(4-chlorophenyl)cyclopropylamine hydrochloride 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-[1-([trans-2-(4-chlorophenyl)cyclopropyl]aminocarbonyl)cyclopentylmethyl]-2-methoxypropionic acid
  参考文献：
  名称：

  Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder

  摘要：

  A series of substituted glutaramides were synthesised using Candoxatrilat 1 as a lead and evaluated for potency against neutral endopeptidase (NEP) as a potential treatment for female sexual arousal disorder (FSAD). In this paper, we describe studies in which we were able to increase NEP activity substantially over the levels reported for previous compounds from this programme by appropriate substitution in both the P'(1) and P'(2) regions. Optimisation led to the 4-chlorophenpropylamide S-30 which was selected as a candidate for further study. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.002
• 作为产物：
  描述：

  trans-tert-butyl 2-(4-chlorophenyl)cyclopropanecarbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 trans-2-(4-chlorophenyl)cyclopropylamine hydrochloride
  参考文献：
  名称：

  Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder

  摘要：

  A series of substituted glutaramides were synthesised using Candoxatrilat 1 as a lead and evaluated for potency against neutral endopeptidase (NEP) as a potential treatment for female sexual arousal disorder (FSAD). In this paper, we describe studies in which we were able to increase NEP activity substantially over the levels reported for previous compounds from this programme by appropriate substitution in both the P'(1) and P'(2) regions. Optimisation led to the 4-chlorophenpropylamide S-30 which was selected as a candidate for further study. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.002

文献信息

• Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors
  作者：Ting-Yueh Tsai、Tsu Hsu、Chiung-Tong Chen、Jai-Hong Cheng、Teng-Kuang Yeh、Xin Chen、Chung-Yu Huang、Chung-Nien Chang、Kai-Chia Yeh、Su-Huei Hsieh、Chia-Hui Chien、Yi-Wei Chang、Chih-Hsiang Huang、Yu-Wen Huang、Chen-Lung Huang、Ssu-Hui Wu、Min-Hsien Wang、Cheng-Tai Lu、Yu-Sheng Chao、Weir-Torn Jiaang

  DOI：10.1016/j.bmc.2009.02.020

  日期：2009.3

  DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC50 values of <100 nM with excellent selectivity over the closely related enzymes, DPP8, DPP-II and FAP. The studies identified a potent and selective DPP-IV inhibitor 24b, which exhibited the ability to both significantly inhibit plasma DPP-IV activity in rats and improve glucose tolerance

  合成了一系列反式-2-芳基-环丙胺衍生的化合物，并评估了其对DPP-IV的生物学活性。构效关系（SAR）导致发现了一系列新的DPP-IV抑制剂，其IC 50值<100 nM，对密切相关的酶DPP8，DPP-II和FAP具有优异的选择性。研究确定了一种有效的选择性DPP-IV抑制剂24b，该抑制剂具有显着抑制大鼠血浆DPP-IV活性并改善瘦小鼠和饮食诱发的肥胖小鼠对葡萄糖的耐受性的能力。
• Compounds Which Potentiate Glutamate Receptor and Uses Thereof in Medicine
  申请人：Andreotti Daniele

  公开号：US20080167351A1

  公开（公告）日：2008-07-10

  This invention relates to potentiation of the glutamate receptor by novel compounds of formula (I): The invention also relates to the use of the derivatives in treating diseases and conditions mediated by potentiation of the glutamate receptor, compositions containing the derivatives and processes for their preparation.

  本发明涉及一些新化合物（I）的谷氨酸受体增强作用，还涉及使用这些衍生物治疗由谷氨酸受体增强介导的疾病和病症、包含这些衍生物的组合物以及它们的制备方法。
• Compounds which potentiate glutamate receptor and uses thereof in medicine
  申请人：Glaxo Group Limited

  公开号：US07790758B2

  公开（公告）日：2010-09-07

  This invention relates to potentiation of the glutamate receptor by novel compounds of formula (I): The invention also relates to the use of the derivatives in treating diseases and conditions mediated by potentiation of the glutamate receptor, compositions containing the derivatives and processes for their preparation.

  本发明涉及公式（I）的新化合物通过增强谷氨酸受体的作用。本发明还涉及利用这些衍生物治疗通过增强谷氨酸受体介导的疾病和病状，包含这些衍生物的组合物和其制备过程。
• [EN] SUBSTITUTED CYCLIC MODULATORS OF PROTEIN PHOSPHATASE 2A (PP2A) AND METHODS USING SAME<br/>[FR] MODULATEURS CYCLIQUES SUBSTITUÉS DE PROTÉINE PHOSPHATASE 2A (PP2A) ET LEURS PROCÉDÉS D'UTILISATION
  申请人：RAPPTA THERAPEUTICS OY

  公开号：WO2022167867A1

  公开（公告）日：2022-08-11

  The present disclosure relates in part to chemical modulators of protein phosphatase 2A (PP2A). The compounds of the present disclosure are useful in treating, preventing, and/or ameliorating cancer, diabetes, autoimmune disease, solid organ transplant rejection, graft vs host disease, chronic obstructive pulmonary disease (COPD), non-alcoholic fatty liver disease, abdominal aortic aneurysm, chronic liver disease, heart failure, neurodegenerative disease, and cardiac hypertrophy.

  本公开涉及部分蛋白磷酸酶2A（PP2A）的化学调节剂。本公开的化合物可用于治疗、预防和/或改善癌症、糖尿病、自身免疫性疾病、固体器官移植排斥、移植物抗宿主病、慢性阻塞性肺疾病（COPD）、非酒精性脂肪性肝病、腹主动脉瘤、慢性肝病、心力衰竭、神经退行性疾病和心肌肥厚。
• Pharmacological and Physicochemical Properties Optimization for Dual-Target Dopamine D₃ (D₃R) and μ-Opioid (MOR) Receptor Ligands as Potentially Safer Analgesics
  作者：Alessandro Bonifazi、Elizabeth Saab、Julie Sanchez、Antonina L. Nazarova、Saheem A. Zaidi、Khorshada Jahan、Vsevolod Katritch、Meritxell Canals、J. Robert Lane、Amy Hauck Newman

  DOI：10.1021/acs.jmedchem.3c00417

  日期：2023.8.10

  agonists with optimized physicochemical properties was designed and synthesized. Combining in vitro cell-based on-target/off-target affinity screening, in silico computer-aided drug design, and BRET functional assays, we identified new structural scaffolds that achieved high affinity and agonist/antagonist potencies for MOR and D3R, respectively, improving the dopamine receptor subtype selectivity (e.g.,

  设计合成了理化性质优化的新一代双靶点μ阿片受体（MOR）激动剂/多巴胺D 3受体（D 3 R）拮抗剂/部分激动剂。结合体外基于细胞的在靶/脱靶亲和力筛选、计算机辅助药物设计和 BRET 功能测定，我们确定了新的结构支架，可实现 MOR 和 D 3 R 的高亲和力和激动剂/拮抗剂效力，分别提高多巴胺受体亚型选择性（例如，D 3 R 优于 D 2 R）并显着提高预测血脑屏障渗透性的中枢神经系统多参数优化得分。我们确定了取代的反式-( 2S , 4R )-吡咯烷和反式-苯基环丙胺作为关键的多巴胺能部分，并将它们连接到源自 MOR 激动剂TRV130 ( 3 ) 或洛哌丁胺 ( 6 ) 的不同阿片类支架。先导化合物46、84、114和121具有通过MOR部分激动作用产生镇痛作用的潜力，并通过D 3 R拮抗作用减少阿片类药物滥用的可能性。此外，外周受限衍生物可能具有治疗炎症和神经性疼痛的适应症。