1H-吲哚-5-碳酰肼 | 406192-82-3

• 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
• 中文名称: 1H-吲哚-5-碳酰肼
• 中文别名: 5-吲哚甲酰肼；吲哚-5-甲酰肼
• 英文名称: 1H-indole-5-carbohydrazide
• 英文别名: indole-5-carbohydrazide；1H-indole-5-carboxylic acid hydrazide
• CAS: 406192-82-3
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: BIQATJKKTYPJHK-UHFFFAOYSA-N

物化性质

• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20°C下，应避光保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  1H-吲哚-5-碳酰肼 在 四(三苯基膦)钯 copper(l) iodide 、 二苯醚 、 sodium hydride 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.74h， 生成 5-(3-(4-isopropoxypyrimidin-2-yl)-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  [EN] AZOLE COMPOUNDS AS PIM INHIBITORS
  [FR] COMPOSÉS D'AZOLE UTILISÉS EN TANT QU'INHIBITEURS DES PIM

  摘要：

  该发明涉及公式I和Ia的双环化合物及其盐。在某些实施例中，该发明涉及Pim-1和/或Pim-2和/或Pim-3蛋白激酶活性或酶功能的抑制剂或调节剂。在更进一步的实施例中，该发明涉及包含本文所披露的化合物的药物组合物，以及它们在预防和治疗Pim激酶相关疾病和病症，尤其是癌症中的用途。

  公开号：

  WO2012129338A1
• 作为产物：
  描述：

  吲哚-5-甲酸乙酯 在 hydrazine hydrate monohydrate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到1H-吲哚-5-碳酰肼
  参考文献：
  名称：

  Identification of N-acylhydrazone derivatives as novel lactate dehydrogenase A inhibitors

  摘要：

  Glycolysis is drastically increased in tumors and it is the main route to energy production with a minor use of oxidative phosphorylation. Among the key enzymes in the glycolytic process, LDH is emerging as one of the most interesting targets for the development of new inhibitors. In this context, in the present work, we carried out a virtual screening procedure followed by chemical modifications of the identified structures according to a "hit-to-lead" process. The effects of the new molecules were preliminary probed against purified human LDH-A. The compounds active at low micromolar level were additionally characterized for their activity on some cellular metabolic processes by using Raji human cell line. Within the series, 1 was considered the best candidate, and a more detailed characterization of its biological properties was performed. In Raji cells exposed to compound 1 we evidenced the occurrence of effects usually observed in cancer cells after LDH-A inhibition: reduced lactate production and NAD/NADH ratio, apoptosis. The flow cytometry analysis of treated cells also showed cell cycle changes compatible with effects exerted at the glycolytic level. Finally, in agreement with the data obtained with other inhibitors or by silencing LDH-A expression, compound 1 was found to increase Rail cells response to some commonly used chemotherapeutic agents. Taken together, all these finding are in support of the LDH-A inhibiting activity of compound 1. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.028

文献信息

• [EN] INHIBITORS OF HEPATITIS C VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2010111483A1

  公开（公告）日：2010-09-30

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种公式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20190127365A1

  公开（公告）日：2019-05-02

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种具有式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• Microwave-Assisted Synthesis and Molecular Recognition Properties of Novel Indole Acylhydrazone Receptors
  作者：Ying Ye、Yourui Suo、Fang Yang、Yongjing Yang、Lijuan Han

  DOI：10.3184/174751915x14306656265736

  日期：2015.5

  Indole acylhydrazones were synthesised in high yields under microwave irradiation By using indole carboxylic acid and 1,4-benzenedialdehyde as starting materials. Their structures were characterised by ¹H NMR, IR, MS spectra and elemental analysis. Selective recognition properties of these receptors have been investigated by UV-Vis spectra titration indicating that these receptors can form 1:1 supramolecular complexes with malic acid, tartaric acid, ascorbic acid and tryptophan.

  以吲哚羧酸和 1,4-苯二甲醛为起始原料，在微波辐照下高产合成了吲哚酰肼。通过 1H NMR、IR、MS 光谱和元素分析对它们的结构进行了表征。通过紫外可见光谱滴定法研究了这些受体的选择性识别特性，结果表明这些受体能与苹果酸、酒石酸、抗坏血酸和色氨酸形成 1:1 的超分子复合物。
• [EN] N-ACYLHYDRAZONE DERIVATIVES USEFUL AS MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] DÉRIVÉS DE N-ACYLHYDRAZONE UTILES EN TANT QUE MODULATEURS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：NEUROSEARCH AS

  公开号：WO2009065850A1

  公开（公告）日：2009-05-28

  This invention relates to N-acylhydrazone derivatives, which are found to be useful as modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  本发明涉及N-酰基腙衍生物，这些衍生物被发现有用作为尼古丁乙酰胆碱受体调节剂。由于它们的药理特性，该发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩相关的疾病或疾病、内分泌疾病或疾病、神经退行性疾病或疾病、炎症、疼痛以及由化学物质滥用终止引起的戒断症状等多种疾病或疾病可能有用。
• 一种抗菌化合物的合成方法
  申请人：中国科学院西北高原生物研究所

  公开号：CN104529863B

  公开（公告）日：2017-09-19

  本发明提供了如式I所示双吲哚酰腙化合物的合成方法，其中，酰基与吲哚基的4、5或6位碳原子相连。本发明合成方法，快速、高效、溶剂用量小，且目标化合物收率较高，为进一步研究式I化合物或相关化合物提供了必要基础。本发明提供的中间体，结构简单、易得，为目标化合物的制备提供了便利。