trans-2-phenyl-cyclopropanecarbohydrazide | 14561-40-1

• 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-phenyl-cyclopropanecarbohydrazide
• 英文别名: trans-2-Phenylcyclopropanecarbohydrazide；(1R,2R)-2-phenylcyclopropane-1-carbohydrazide
• CAS: 14561-40-1
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: LVPLGMIOSVEITG-DTWKUNHWSA-N

物化性质

• 熔点：
  124-126.5 °C(Solv: water (7732-18-5))
• 沸点：
  386.1±22.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

制备方法与用途

该产品可用作反应试剂或用于制备苯基环丙基吲哚羧酸，作为 umifenvir 类似物，并评估其细胞毒性及抗病毒活性。

反应信息

• 作为反应物：
  描述：

  N-(4-acetylphenyl)furan-2-carboxamide 、 trans-2-phenyl-cyclopropanecarbohydrazide 以 乙醇 为溶剂， 反应 22.0h， 以78%的产率得到N-[4-[C-methyl-N-[[(1R,2R)-2-phenylcyclopropanecarbonyl]amino]carbonimidoyl]phenyl]furan-2-carboxamide
  参考文献：
  名称：

  Lead optimization of an acylhydrazone scaffold possessing antiviral activity against Lassa virus

  摘要：

  Previously we reported the optimization of antiviral scaffolds containing benzimidazole and related heterocycles possessing activity against a variety of arenaviruses. These series of compounds were discovered through an HTS campaign of a 400,000 small molecule library using lentivirus-based pseudotypes incorporated with the Lassa virus envelope glycoprotein (LASV GP). This screening also uncovered an alternate series of very potent arenavirus inhibitors based upon an acylhydrazone scaffold. Subsequent SAR analysis of this chemical series involved various substitutions throughout the chemical framework along with assessment of the preferred stereochemistry. These studies led to an optimized analog (ST-161) possessing subnanomolar activity against LASV and submicromolar activity against a number of other viruses in the Arenaviridae family. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.103
• 作为产物：
  描述：

  (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 在 N,N'-羰基二咪唑 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 生成 trans-2-phenyl-cyclopropanecarbohydrazide
  参考文献：
  名称：

  COMPOUNDS, COMPOSITIONS, AND METHODS

  摘要：

  The present disclosure relates generally to small molecule modulators of ion channels (TMEM-175) and their use as therapeutic agents.

  公开号：

  WO2024108155A2

文献信息

• [EN] HYDRAZONE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS D'HYDRAZONE ET LEUR UTILISATION
  申请人：STEIN PHILIP

  公开号：WO2010132615A1

  公开（公告）日：2010-11-18

  The present invention relates to hydrazone compounds of Formula I: (I) and pharmaceutically acceptable salts and stereoisomers thereof, wherein R1, R2, R3, R4, L1, and L2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

  本发明涉及式I的腙化合物：(I)及其药用可接受的盐和立体异构体，其中R1、R2、R3、R4、L1和L2的定义如规范中所述。该发明还涉及将式I的化合物用作TRPM5蛋白的抑制剂。
• Hydrazone Compounds and Their Use
  申请人：STEIN Philip

  公开号：US20110033393A1

  公开（公告）日：2011-02-10

  The present invention relates to hydrazone compounds of Formula I: and pharmaceutically acceptable salts and stereoisomers thereof, wherein R 1 , R 2 , R 3 , R 4 , L 1 , and L 2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

  本发明涉及式I的腙化合物及其药用可接受的盐和立体异构体，其中R1、R2、R3、R4、L1和L2的定义如规范中所述。本发明还涉及将式I的化合物用作TRPM5蛋白质的抑制剂。
• Lead optimization of an acylhydrazone scaffold possessing antiviral activity against Lassa virus
  作者：James R. Burgeson、Dima N. Gharaibeh、Amy L. Moore、Ryan A. Larson、Sean M. Amberg、Tove’ C. Bolken、Dennis E. Hruby、Dongcheng Dai

  DOI：10.1016/j.bmcl.2013.08.103

  日期：2013.11

  Previously we reported the optimization of antiviral scaffolds containing benzimidazole and related heterocycles possessing activity against a variety of arenaviruses. These series of compounds were discovered through an HTS campaign of a 400,000 small molecule library using lentivirus-based pseudotypes incorporated with the Lassa virus envelope glycoprotein (LASV GP). This screening also uncovered an alternate series of very potent arenavirus inhibitors based upon an acylhydrazone scaffold. Subsequent SAR analysis of this chemical series involved various substitutions throughout the chemical framework along with assessment of the preferred stereochemistry. These studies led to an optimized analog (ST-161) possessing subnanomolar activity against LASV and submicromolar activity against a number of other viruses in the Arenaviridae family. (C) 2013 Elsevier Ltd. All rights reserved.
• COMPOUNDS, COMPOSITIONS, AND METHODS
  申请人：[en]DENALI THERAPEUTICS INC.

  公开号：WO2024108155A2

  公开（公告）日：2024-05-23

  The present disclosure relates generally to small molecule modulators of ion channels (TMEM-175) and their use as therapeutic agents.