1-甲基吲哚-2-甲酰肼 | 56809-86-0

• 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: 1-甲基吲哚-2-甲酰肼
• 英文名称: 1-methyl-1H-indole-2-carbohydrazide
• 英文别名: 1-methylindole-2-carbohydrazide
• CAS: 56809-86-0
• 化学式: C₁₀H₁₁N₃O
• mdl: MFCD00463397
• 分子量: 189.217
• InChiKey: UCYCLKHTMATMLF-UHFFFAOYSA-N

物化性质

• 熔点：
  156.2-157 °C(Solv: methanol (67-56-1))
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基吲哚-2-甲酰肼 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-[2-(N-methylindole)]-4H-1,3,4-oxadiazin-5(6H)-one
  参考文献：
  名称：

  合成新的吲哚基-1,3,4-恶二唑和恶二嗪衍生物。潜在的单胺氧化酶抑制剂活性

  摘要：

  制备了新的吲哚基-1,3,4-恶二唑和恶二嗪衍生物作为可逆的单胺氧化酶抑制剂。化合物5-（3-甲基吲哚基）-1,3,4-恶二唑-2（3 H）one被证明是一种良好的单胺氧化酶B抑制剂。

  DOI：

  10.1002/jhet.5570340523
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-甲基吲哚-2-甲酰肼
  参考文献：
  名称：

  Synthesis and antioxidant and antimicrobial evaluation of novel 4-substituted-1H-1,2,4-triazole derivatives

  摘要：

  合成了一系列 4-苄基/苯基-3-(1-甲基-1H-吲哚-2-基)-1H- 1,2,4-三唑-5(4H)-硫酮（4a,b）和 2-{4-[苄基/苯基-5-（取代的苄基硫代）]-4H-1,2、4-三唑-3-基}-1-甲基-1H-吲哚衍生物（5a-p）的合成，并对其体外清除 DPPH 和超氧自由基、抑制脂质过氧化反应的效果及其抗菌特性进行了评估。 结果发现，含有 1,2,4-三唑-5(4H)-硫酮分子的化合物（4a,b）的 DPPH 自由基清除能力与 BHT 相当。 在抗菌特性方面，化合物 5k 对所有测试微生物都显示出轻微的抗菌活性。

  DOI：

  10.3906/kim-1202-62

文献信息

• Indole-3-carbinol and 1,3,4-Oxadiazole Hybrids: Synthesis and Study of Anti-Proliferative and Anti-Microbial Activity
  作者：Nikhila Gokhale、Naveen Panathur、Udayakumar Dalimba、Manjunatha Kumsi

  DOI：10.1071/ch15116

  日期：——

  In the present study, molecular hybrids of indole-3-carbinol and 1,3,4-oxadiazole-2-thiols have been designed and synthesized. The thiol analogues consisted of diversely substituted benzyl and alkyl groups with different electronic properties. The structures of all the newly synthesized scaffolds and target compounds were ascertained using 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. All the final compounds were screened in vitro for their anti-proliferative and anti-microbial activity. Three compounds showed excellent anti-proliferative activity with more than 70 % cell growth inhibition against three cancer cell lines, HepG2 (human liver hepatocellular carcinoma), HeLa (human cervix carcinoma), and MCF-7 (human breast carcinoma). In the anti-microbial studies, compounds with electron-withdrawing fluoro or nitro substituent displayed appreciable activity similar to that of standard drugs. Also, the final compounds are non-toxic to non-cancerous Vero cell line.

  本研究设计并合成了吲哚-3-甲醇和 1,3,4-噁二唑-2-硫醇的分子杂交体。硫醇类似物由具有不同电子特性的苄基和烷基取代组成。利用 1H NMR、13C NMR、质谱和元素分析确定了所有新合成支架和目标化合物的结构。对所有最终化合物进行了体外抗增殖和抗微生物活性筛选。三种化合物显示出卓越的抗增殖活性，对三种癌细胞系（HepG2（人肝肝细胞癌）、HeLa（人宫颈癌）和 MCF-7（人乳腺癌））的细胞生长抑制率超过 70%。在抗微生物研究中，具有吸电子氟或硝基取代基的化合物显示出与标准药物相似的显著活性。此外，最终化合物对非癌 Vero 细胞系无毒。
• Synthesis and antiproliferative activity of salicylidenehydrazones based on indole-2(3)-carboxylic acids
  作者：Andrey G. Vasin、Lyubov G. Dezhenkova、Ivan V. Ivanov、Alexander M. Scherbakov、Andrey E. Shchekotikhin

  DOI：10.1007/s10593-020-02724-2

  日期：2020.6

  A series of indole-2(3)-carboxylic acid hydrazones were synthesized and their antiproliferative activity was studied for the K562 leukemia, MCF7 breast adenocarcinoma, and HCT116 colon carcinoma cell lines and resistant HCT116p53KO subline in order to preliminary screen biological properties and to reveal the role of the aldehyde fragment and heterocycle in the ability of compounds to inhibit tumor

  合成了一系列吲哚-2（3）-羧酸，并对其在K562白血病，MCF7乳腺腺癌和HCT116结肠癌细胞系及耐药HCT116p53KO亚系中的抗增殖活性进行了初步筛选，以揭示其生物学特性。醛片段和杂环在化合物抑制肿瘤生长能力中的作用。已经鉴定出许多以亚微摩尔浓度抑制肿瘤细胞生长的衍生物，有望进一步优化和深入研究抗肿瘤特性。
• Novel Hydroxamic Acids Containing Aryl-Substituted 1,2,4- or 1,3,4-Oxadiazole Backbones and an Investigation of Their Antibiotic Potentiation Activity
  作者：Anastasia A. Zhukovets、Vladimir V. Chernyshov、Aidar Z. Al’mukhametov、Tatiana A. Seregina、Svetlana V. Revtovich、Mariia A. Kasatkina、Yulia E. Isakova、Vitalia V. Kulikova、Elena A. Morozova、Anastasia I. Cherkasova、Timur A. Mannanov、Anastasia A. Anashkina、Pavel N. Solyev、Vladimir A. Mitkevich、Roman A. Ivanov

  DOI：10.3390/ijms25010096

  日期：——

  activity, and antibiotic potentiation. Some of the hydroxamic acids we obtained (9c, 9d, 23a, 23c, 30b, 36) showed significant potentiation in nalidixic acid, rifampicin, and kanamycin against the growth of laboratory-strain Escherichia coli MG1655. Two lead compounds (9c, 9d) significantly reduced Pseudomonas aeruginosa ATCC 27853 growth in the presence of nalidixic acid and rifampicin.

  UDP-3-O-(R-3-羟基肉豆蔻酰)-N-乙酰氨基葡萄糖脱乙酰酶 (LpxC) 是一种锌酰胺酶，可催化脂质 A 生物合成的第二步，脂质 A 是革兰氏阴性细菌的外膜必需结构成分。该酶的抑制剂可分为两大类：非异羟肟酸盐抑制剂和异羟肟酸盐抑制剂，鉴于活性位点中 Zn2+ 的螯合，后者是最有效的。含有丁二炔或乙炔尾和磺酸头的化合物，以及异羟肟酸的恶唑啉衍生物，是具有最深远抗菌活性的LpxC抑制剂之一。本文描述了含有 1,2,4- 和 1,3,4-恶二唑核心的异羟肟酸生物电子等排的新型功能衍生物的合成及其细胞毒性、抗菌活性和抗生素增强作用的研究。我们获得的一些异羟肟酸（9c、9d、23a、23c、30b、36）在萘啶酸、利福平和卡那霉素中对实验室菌株大肠杆菌 MG1655 的生长表现出显着的增强作用。在萘啶酸和利福平存在下，两种先导化合物 (9c、9d) 显着降低铜绿假单胞菌 ATCC 27853
• Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition
  作者：Naveen Panathur、Udayakumar Dalimba、Pulla Venkat Koushik、Mallika Alvala、Perumal Yogeeswari、Dharmarajan Sriram、Vijith Kumar

  DOI：10.1016/j.ejmech.2013.08.018

  日期：2013.11

  In our pursuit to develop new potential anticancer leads, we designed a combination of structural units of indole and substituted triazole; and a library of 1-1-methyl-2-[4-phenyl-5-(propan-2-ylsulfanyl)-4H-1,2,4-triazol-3-yl]-1H-indol-3-yl}methanamine derivatives was synthesized and characterized. Cytotoxic evaluations of these molecules over a panel of three human cancer cell lines were carried out. Few molecules exhibited potent growth inhibitory action against the treated cancer cell lines at lower micro molar concentration. An in vitro assay investigation of these active compounds using recombinant human SIRT1 enzyme showed that one of the compounds (IT-14) inhibited the deacetylation activity of the enzyme. The in vivo study of IT-14 exemplified its promising action by reducing the prostate weight to the body weight ratio in prostate hyperplasia animal models. A remarkable decrease in the disruption of histoarchitecture of the prostate tissues isolated from IT-14 treated animal compared to that of the positive control was observed. The molecular interactions with SIRT1 enzyme were also supported by molecular docking simulations. Hence this compound can act as a lead molecule to treat prostatic hyperplasia. (C) 2013 Elsevier Masson SAS. All rights reserved.
• A Simple Preparation of 4-Oxo-3,4-dihydro-5<i>H</i>-pyridazino[4,5-<i>b</i>]indoles
  作者：A. Monge、I. Aldana、I. Lezamiz、E. Fernández-Alvarez

  DOI：10.1055/s-1984-30765

  日期：——