N'-(1H-indole-2-carbonyl)-1H-indole-2-carbohydrazide

• 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: N'-(1H-indole-2-carbonyl)-1H-indole-2-carbohydrazide
• 英文别名: N'-(1H-indole-2-carbonyl)-1H-indole-2-hydrazide
• 化学式: C₁₈H₁₄N₄O₂
• 分子量: 318.335
• InChiKey: YEHAVWCDKXUSPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N'-(1H-indole-2-carbonyl)-1H-indole-2-carbohydrazide
  参考文献：
  名称：

  Pentafluorophenyl ester activation for the preparation of N,N′-diaroylhydrazines

  摘要：

  Procedures are reported for the preparation of N,N'-diaroylhydrazines using pentafluorophenyl (Pfp) ester activation of aryl carboxylic acids. Mild conditions which avoid intermediate protection of ring substituents, allows the synthesis of both symmetrical and unsymmetrical diaroylhydrazines in high yields. The recent discovery of potent HIV-1 integrase inhibition by N,N'-bis-salicylhydrazine (1) highlights the potential importance of this class of compounds. The stability of pre-activated Pfp ester intermediates and the facility with which N,N'-diaroylhydrazines can be synthesized using this procedure (stirring at room temperature in DMF) may make the method particularly attractive for synthesis of hydrazide libraries.

  DOI：

  10.1016/s0040-4020(97)00149-x

文献信息

• Investigation of interaction of benzoquinones and naphthoquinones with substituted hydrazides
  作者：Alaa A. Hassan、Yusria R. Ibrahim、Ahmed M. Shawky

  DOI：10.1002/jhet.278

  日期：——

  and 2,3-dichloro-1,4-naphthoquinone initiates the formation of benzo[e][1,3,4]oxadiazine and benzo- as well as naphthoxadiazepine derivatives. On the other hand, substituted hydrazides attack 1,4-naphthoquinone-2,3-dicarbonitrile to form benzo[f]indazole-4,9-dione derivatives. A rationale for the conversions observed is presented. J. Heterocyclic Chem., 2010.

  取代的酰肼对C-2，C-3的亲核攻击 2,3,5,6-四氯-1,4-苯醌和2,3-二氯-1,4-萘醌可引发苯并[e] [1,3,4]恶二嗪和苯并-以及萘恶二氮杂卓衍生物的形成。另一方面，取代的酰肼会进攻1,4-萘醌-2,3-二甲腈形成苯并[f]吲唑-4,9-二酮衍生物。提供了观察到的转换的原理。J.杂环化​​学.2010。
• Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities
  作者：Mohamed Abdel-Aziz、Gamal El-Din A. Abuo-Rahma、Alaa A. Hassan

  DOI：10.1016/j.ejmech.2009.01.032

  日期：2009.9

  prepared compounds 4a–d, 5a–d and 11a–d were evaluated each for antidepressant activity using tail suspension behavioral despair test and anticonvulsant activity against PTZ induced seizures in mice. Compounds 4a and 4b induced markedly antidepressant activity compared to imipramine, and their activities as antidepressant nearly equal twice the activity of imipramine at 10 mg kg−1 dose level. On the

  取代的羧酸酰肼1a - d与乙撑四碳腈2在二甲基甲酰胺中反应，形成二酰基肼4a - d和5-氨基-1-取代的吡唑-3,3,4-三腈5a - d。另一方面，1a – d与（E）-2,3-二氰基丁二酸二乙酯3反应，分别得到恶二唑衍生物10a – d和吡唑酮衍生物11a – d。所制备的化合物4A - ð，使用尾部悬架行为绝望测试评估了5a – d和11a – d的抗抑郁活性，以及​​对小鼠PTZ诱发的癫痫发作的抗惊厥活性。与丙咪嗪相比，化合物4a和4b诱导了显着的抗抑郁活性，并且在10 mg kg -1剂量水平下，它们作为抗抑郁药的活性几乎等于丙咪嗪的活性的两倍。另一方面，化合物11b，11a和11d对以20 mg kg -1的剂量ip注射PTZ引起的阵挛性癫痫发作表现出显着的保护作用。。抗惊厥活性的结果是几乎接近苯巴比妥钠的剂量水平30毫克千克-1和比以30mg公斤的剂量水平苯妥英钠更有效-1。
• Reactions of Substituted Carbohydrazides with Electron-poor Olefins
  作者：Alaa A. Hassan、Yusria R. Ibrahim、Ahmed M. Shawky

  DOI：10.1515/znb-2008-0813

  日期：2008.8.1

  Substituted carbohydrazides 1a - e reacted with ethenetetracarbonitrile (2) in dimethylformamide with formation of diacylhydrazines 4a - e and 5-amino-1-substiuted pyrazole-3,3,4-tricarbonitriles 5a - e. On the other hand, 1a-c reacted with diethyl (E)-2,3-dicyanobutenedioate (3) to give oxadiazinone and pyrazolone derivatives 12a - e and 13a - e, respectively.

  取代的碳酰肼 1a-e 在二甲基甲酰胺中与乙烯四甲腈 (2) 反应，形成二酰基肼 4a-e 和 5-氨基-1-取代的吡唑-3,3,4-三甲腈 5a-e。另一方面，1a-c 与 (E)-2,3-二氰基丁二酸二乙酯 (3) 反应，分别得到恶二嗪酮和吡唑啉酮衍生物 12a-e 和 13a-e。
• Pentafluorophenyl ester activation for the preparation of N,N′-diaroylhydrazines
  作者：He Zhao、Terrence R. Burke

  DOI：10.1016/s0040-4020(97)00149-x

  日期：1997.3

  Procedures are reported for the preparation of N,N'-diaroylhydrazines using pentafluorophenyl (Pfp) ester activation of aryl carboxylic acids. Mild conditions which avoid intermediate protection of ring substituents, allows the synthesis of both symmetrical and unsymmetrical diaroylhydrazines in high yields. The recent discovery of potent HIV-1 integrase inhibition by N,N'-bis-salicylhydrazine (1) highlights the potential importance of this class of compounds. The stability of pre-activated Pfp ester intermediates and the facility with which N,N'-diaroylhydrazines can be synthesized using this procedure (stirring at room temperature in DMF) may make the method particularly attractive for synthesis of hydrazide libraries.