1H-indole-2-carboxylic acid benzylidene-hydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1H-indole-2-carboxylic acid benzylidene-hydrazide
• 英文别名: (E)-N'-benzylidene-1H-indole-2-carbohydrazide；N-[(E)-benzylideneamino]-1H-indole-2-carboxamide
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: SYUQFFCOGGAGKC-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-indole-2-carboxylic acid benzylidene-hydrazide 、 苯甲酰氯 以50%的产率得到
  参考文献：
  名称：

  VEGA A. M.; PALOP J. A.; MARTINEZ M. T.; ALVAREZ E. F., J. HETEROCYCL. CHEM., 1980, 17, NO 2, 249-256

  摘要：

  DOI：
• 作为产物：
  描述：

  吲哚-2-羧酸甲酯 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 1H-indole-2-carboxylic acid benzylidene-hydrazide
  参考文献：
  名称：

  Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

  摘要：

  2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their alpha-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 +/- 0.11-226.4 +/- 6.8 mu M was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0 +/- 6.3 mu M). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of nu(C=O), nu(N=C) and nu(CH) (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.09.001

文献信息

• Substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：——

  公开号：US20020128292A1

  公开（公告）日：2002-09-12

  The present invention is directed to substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs thereof, represented by the general Formula I: 1 wherein X, Ar 1 , R 2 -R 6 and R 12 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. The compounds of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的吲哚-2-羧酸亚苄基肼及其类似物，其由通式I表示： 1 其中X，Ar 1 ，R 2 -R 6 和R 12 的定义如本文中所述。本发明还涉及发现具有I式的化合物是半胱天冬酶的激活剂和凋亡的诱导剂。本发明的化合物可用于诱导在异常细胞不受控制的生长和扩散发生的多种临床状况中的细胞死亡。
• Discovery of heterocyclic carbohydrazide derivatives as novel selective fatty acid amide hydrolase inhibitors: design, synthesis and anti-neuroinflammatory evaluation
  作者：Yanguo Shang、Qingjing Hao、Kaixuan Jiang、Mengting He、Jinxin Wang

  DOI：10.1016/j.bmcl.2020.127118

  日期：2020.5

  promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound 26 showed strong inhibition against human FAAH

  Fatty acid amide hydrolase (FAAH) is a promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound
• On the Synthesis and Reactions of Indole-2-carboxylic Acid Hydrazide
  作者：Abd El-Wareth、A. O. Sarhan

  DOI：10.1007/s007060170091

  日期：2001.6

   Indole-2-carboxylic acid hydrazide was prepared and allowed to react with aromatic aldehydes in acidic medium to give the corresponding hydrazone derivatives in good yields. The hydrazones were cyclized to indolo[2,3- d ]pyridazine derivatives by refluxing with acetyl chloride. The indole carbohydrazide was converted to 2-triazolylindoles which acted as starting materials for several indole derivatives

   制备吲哚-2-羧酸酰肼，并使其在酸性介质中与芳族醛反应，以高收率得到相应的衍生物。通过与乙酰氯回流，将hydr环环化为吲哚[2，3- d ]哒嗪衍生物。吲哚碳酰肼被转化为2-三唑基吲哚，这是几种吲哚衍生物的起始原料。还制备了许多新的吲哚衍生物并进行了结构确认。
• Compounds and methods for regulation of spermatid differentiation
  申请人：Steller Hermann

  公开号：US20050120397A1

  公开（公告）日：2005-06-02

  The present invention provides methods for the regulation of spermatid differentiation. This invention also provides applications of regulated spermatid differentiation, including the treatment of infertility, contraception and pest control. This invention also describes agents for effecting such methods and compositions comprising same.

  本发明提供了调节精子分化的方法。本发明还提供了调节精子分化的应用，包括治疗不育症、避孕和虫害防治。本发明还描述了实现这些方法的制剂和包含这些制剂的组合物。
• MONGE, A.;PALOP, J. A.;TABAR, P.;FERNANDEZ-ALVAREZ, E., J. HETEROCYCL. CHEM., 1984, 21, N 2, 397-400
  作者：MONGE, A.、PALOP, J. A.、TABAR, P.、FERNANDEZ-ALVAREZ, E.

  DOI：——

  日期：——