(+)-trans-2-phenylcyclopropanecarboxylic acid (2-hydroxy-1-phenylethyl)amide | 928055-00-9

• 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-phenylcyclopropanecarboxylic acid (2-hydroxy-1-phenylethyl)amide
• 英文别名: (1S,2S)-N-((R)-2-hydroxy-1-phenylethyl)-2-phenylcyclopropanecarboxamide；(1S,2S)-N-(2-hydroxy-1-phenylethyl)-2-phenylcyclopropanecarboxamide；(1S,2S)-2-phenyl-cyclopropanecarboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide；(1S,2S)-N-[(1R)-2-hydroxy-1-phenylethyl]-2-phenylcyclopropane-1-carboxamide
• CAS: 928055-00-9
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: UTNWTGFEJJAUHD-IKGGRYGDSA-N

物化性质

• 沸点：
  532.2±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-trans-2-phenylcyclopropanecarboxylic acid (2-hydroxy-1-phenylethyl)amide 在 硫酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以98%的产率得到(1S,2S)-2-phenylcyclopropane-1-carboxylic acid
  参考文献：
  名称：

  通过合理的针对性重用方法发现基于碳酸酐酶抑制剂的新型潜在抗感染化合物

  摘要：

  在学术界，化合物回收代表了另一种药物发现策略，可从内部可用的化合物库中识别新的药物靶标。在此，我们报告了一种合理的基于目标药物的重新定位方法的应用，该方法可为我们内部的化合物收集找到多种应用。碳酸酐酶（CA，EC 4.2.1.1）金属酶超家族被确定为我们化合物的潜在目标。彻底验证的对接筛选方案与针对各种CA家族和同工型的体外测定相结合，使我们能够鉴定出两种史无前例的化学型作为CA抑制剂。

  DOI：

  10.1002/cmdc.201600180
• 作为产物：
  描述：

  2-苯基环丙烷羧酸乙酯 在 甲醇 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (-)-trans-2-phenylcyclopropanecarboxylic acid (2-hydroxy-1-phenylethyl)amide 、 (+)-trans-2-phenylcyclopropanecarboxylic acid (2-hydroxy-1-phenylethyl)amide
  参考文献：
  名称：

  [EN] KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE
  [FR] INHIBITEURS DE KDM1A POUR LE TRAITEMENT D'UNE MALADIE

  摘要：

  本文披露了新化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制KDMIA的方法，以及增加人类或动物主体中γ球蛋白基因表达的方法，用于治疗镰状细胞病等疾病。

  公开号：

  WO2014164867A1

文献信息

• 5-HT2C Receptor Agonists as Anorectic Agents
  申请人：Kozikowski Alan

  公开号：US20090203750A1

  公开（公告）日：2009-08-13

  This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.

  本发明涉及调节5-HT2家族受体的化合物，特别是调节5-HT2C受体的化合物。本发明的化合物包括5-HT2C受体的激动剂和选择性激动剂。本发明的化合物包括5-HT2C受体的选择性激动剂，其在5-HT2A受体和/或5-HT2B受体上表现出显著较少或无激动剂活性。本发明的化合物包括式I和药学上可接受的盐、酯和溶剂（包括水合物），其中变量在本规范中定义。
• Discovery and optimization of Lu AF58801, a novel, selective and brain penetrant positive allosteric modulator of alpha-7 nicotinic acetylcholine receptors: Attenuation of subchronic phencyclidine (PCP)-induced cognitive deficits in rats following oral administration
  作者：Jørgen Eskildsen、John P. Redrobe、Anette G. Sams、Kim Dekermendjian、Morten Laursen、Jette B. Boll、Roger L. Papke、Christoffer Bundgaard、Kristen Frederiksen、Jesper F. Bastlund

  DOI：10.1016/j.bmcl.2013.11.022

  日期：2014.1

  In this Letter, we describe a chemical lead optimization campaign starting from a novel, weak alpha 7 nicotinic acetylcholine receptor positive allosteric modulator (PAM) hit from a HTS screen. Exploration of the structure-activity relationships for alpha 7 PAM potency, intrinsic hepatic clearance, the structure-property relationships for lipophilicity, and thermodynamic solubility, led to the identification of Lu AF58801: a potent, orally available, brain penetrant PAM of the alpha 7 nicotinic acetylcholine receptor, showing efficacy in a novel object recognition task in rats treated subchronically with phencyclidine (PCP). (C) 2013 Elsevier Ltd. All rights reserved.
• Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action
  作者：Sung Jin Cho、Niels H. Jensen、Toru Kurome、Sudhakar Kadari、Michael L. Manzano、Jessica E. Malberg、Barbara Caldarone、Bryan L. Roth、Alan P. Kozikowski

  DOI：10.1021/jm801354e

  日期：2009.4.9

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.
• WO2007/25144
  申请人：——

  公开号：——

  公开（公告）日：——
• NEW POSITIVE ALLOSTERIC MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTOR
  申请人：H. Lundbeck A/S

  公开号：EP2928860A1

  公开（公告）日：2015-10-14