(1S,2R)-1-ethyl-2-phenylcyclopropanecarboxylic acid | 1613475-28-7

• 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: (1S,2R)-1-ethyl-2-phenylcyclopropanecarboxylic acid
• 英文别名: (1S,2R)-1-ethyl-2-phenyl-cyclopropanecarboxylic acid；(1S,2R)-1-ethyl-2-phenylcyclopropane-1-carboxylic acid
• CAS: 1613475-28-7
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: MHNILVJIEROMSM-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-ethyl-2-phenylcyclopropanecarboxylic acid 在 盐酸 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 36.0h， 生成 (1S,2R)-1-ethyl-2-phenylcyclopropanamine hydrochloride
  参考文献：
  名称：

  Cyclopropylamine derivatives useful as inhibitors of histone demethylases kdm1a

  摘要：

  本发明涉及一般式(I)的环丙基衍生物，其中A、R1和R2如规范中所定义。本申请还涉及含有这种化合物的药物组合物以及它们在治疗中的应用。

  公开号：

  EP2740474A1
• 作为产物：
  描述：

  (R)-环氧苯乙烷 在 正丁基锂 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 2.91h， 生成 (1S,2R)-1-ethyl-2-phenylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis, biological activity and mechanistic insights of 1-substituted cyclopropylamine derivatives: A novel class of irreversible inhibitors of histone demethylase KDM1A

  摘要：

  Histone demethylase KDM1A (also known as LSD1) has become an attractive therapeutic target for the treatment of cancer as well as other disorders such as viral infections. We report on the synthesis of compounds derived from the expansion of tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. These compounds, which are substituted on the cyclopropyl core moiety, were evaluated for their ability to inhibit KDM1A in vitro as well as to function in cells by modulating the expression of Gfi-1b, a well recognized KDM1A target gene. The molecules were all found to covalently inhibit KDM1A and to become increasingly selective against human monoamine oxidases MAO A and MAO B through the introduction of bulkier substituents on the cyclopropylamine ring. Structural and biochemical analysis of selected trans isomers showed that the two stereoisomers are endowed with similar inhibitory activities against KDM1A, but form different covalent adducts with the FAD co-enzyme. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.068

文献信息

• Discovery of New Potential Anti-Infective Compounds Based on Carbonic Anhydrase Inhibitors by Rational Target-Focused Repurposing Approaches
  作者：Giannamaria Annunziato、Andrea Angeli、Francesca D'Alba、Agostino Bruno、Marco Pieroni、Daniela Vullo、Viviana De Luca、Clemente Capasso、Claudiu T. Supuran、Gabriele Costantino

  DOI：10.1002/cmdc.201600180

  日期：2016.9.6

  In academia, compound recycling represents an alternative drug discovery strategy to identify new pharmaceutical targets from a library of chemical compounds available in house. Herein we report the application of a rational target‐based drug‐repurposing approach to find diverse applications for our in‐house collection of compounds. The carbonic anhydrase (CA, EC 4.2.1.1) metalloenzyme superfamily

  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。
• [EN] CYCLOPROPYLAMINE DERIVATIVES USEFUL AS INHIBITORS OF HISTONE DEMETHYLASES KDM1A<br/>[FR] DÉRIVÉS DE CYCLOPROPYLAMINE UTILES EN TANT QU'INHIBITEURS DE HISTONE DÉMÉTHYLASES KDM1A
  申请人：ISTITUTO EUROP DI ONCOLOGIA S R L

  公开号：WO2014086790A1

  公开（公告）日：2014-06-12

  (I) The present invention relates to cyclopropyl derivatives of general formula (I), wherein A, R1, and R2 are as defined in the specification. The present application also relates to pharmaceutical compositions containing such compounds and to their use in therapy.

  本发明涉及一般式(I)的环丙基衍生物，其中A、R1和R2如规范中定义。本申请还涉及含有这类化合物的药物组合物以及它们在治疗中的应用。
• Cyclopropylamine derivatives useful as inhibitors of histone demethylases kdm1a
  申请人：Instituto Europeo di Oncologia S.r.l.

  公开号：EP2740474A1

  公开（公告）日：2014-06-11

  The present invention relates to cyclopropyl derivatives of general formula (I), wherein A, R1, and R2 are as defined in the specification. The present application also relates to pharmaceutical compositions containing such compounds and to their use in therapy.

  本发明涉及一般式(I)的环丙基衍生物，其中A、R1和R2如规范中所定义。本申请还涉及含有这种化合物的药物组合物以及它们在治疗中的应用。
• Rational Design, Synthesis, and Preliminary Structure–Activity Relationships of α-Substituted-2-Phenylcyclopropane Carboxylic Acids as Inhibitors of <i>Salmonella typhimurium</i> <i>O</i>-Acetylserine Sulfhydrylase
  作者：Marco Pieroni、Giannamaria Annunziato、Claudia Beato、Randy Wouters、Roberto Benoni、Barbara Campanini、Thelma A. Pertinhez、Stefano Bettati、Andrea Mozzarelli、Gabriele Costantino

  DOI：10.1021/acs.jmedchem.5b01775

  日期：2016.3.24

  affects the physiology of unicellular organisms. As a continuation of our efforts toward the synthesis of OASS inhibitors, in this work we have used a combination of computational and spectroscopic approaches to rationally design, synthesize, and test a series of substituted 2-phenylcyclopropane carboxylic acids that bind to the two S. typhymurium OASS isoforms at nanomolar concentrations.

  半胱氨酸是构成对生物至关重要的几种生物分子的基础。O催化半胱氨酸生物合成的最后一步-乙酰丝氨酸磺化酶（OASS）是高度保守的吡pyr醛5'-磷酸（PLP）依赖性酶，存在于细菌，植物和线虫的不同同工型中，但在哺乳动物中不存在。除了半胱氨酸的生物合成外，OASS还可以在细菌中发挥一系列“月光化”活动，例如转录调节，接触依赖性生长抑制，成群运动和诱导抗生素抗性。因此，发现能够抑制OASS的分子将是揭示该蛋白如何影响单细胞生物生理的有价值的工具。为了继续努力合成OASS抑制剂，在这项工作中，我们使用了计算和光谱方法相结合的方法来合理地设计，合成，鼠伤寒沙门氏菌OASS同工型在纳摩尔浓度。
• CYCLOPROPYLAMINE DERIVATIVES USEFUL AS INHIBITORS OF HISTONE DEMETHYLASES KDM1A
  申请人：INSTITUTO EUROPEO DI ONCOLOGIA S.R.L.

  公开号：US20150315126A1

  公开（公告）日：2015-11-05

  The present invention relates to cyclopropyl derivatives of general formula (I), wherein A, R 1 , and R 2 are as defined in the specification. The present application also relates to pharmaceutical compositions containing such compounds and to their use in therapy.

  本发明涉及一般式(I)的环丙基衍生物，其中A、R1和R2如规范中所定义。本申请还涉及含有这种化合物的药物组合物以及它们在治疗中的使用。