5-methyl-3-phenyl-indole-2-carboxylic acid hydrazide | 105492-13-5

• 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: 5-methyl-3-phenyl-indole-2-carboxylic acid hydrazide
• 英文别名: 5-methyl-3-phenyl-1H-indole-2-carboxyhydrazide；5-methyl-3-phenyl-1H-indole-2-carbohydrazide；5-methyl-3-phenylindole-2-carboxyhydrazide
• CAS: 105492-13-5
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: VVXDYTAJHUUMKL-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-3-phenyl-indole-2-carboxylic acid hydrazide 在 溶剂黄146 、 sodium nitrite 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 7.5h， 生成 10-methyl-6,7-dihydroindolo[2,3-c]isoquinolin-5-one
  参考文献：
  名称：

  Hiremath, Shiva Yogi P.; Badami, Prema S.; Purohit, Muralidhar G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1235 - 1238

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 盐酸 、 肼 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 11.0h， 生成 5-methyl-3-phenyl-indole-2-carboxylic acid hydrazide
  参考文献：
  名称：

  Discovery and SAR of indole-2-carboxylic acid benzylidene-hydrazides as a new series of potent apoptosis inducers using a cell-based HTS assay

  摘要：

  A series of indole-2-carboxylic acid benzylidene-hydrazides has been identified as a new class of potent apoptosis inducers through a novel cell-based caspase HTS assay. The screening hit, 5-chloro-3-methyl-indole-2-carboxylic acid (4-nitrobenzylidene)-hydrazide (3a), was found to arrest T47D cells in G(2)/M and to induce apoptosis as measured by the flow cytometric analysis assay. A SAR study was carried out by modification of the substitutions on the indole and benzene rings. Substitution at the 3-position of the indole ring was found to be important for apoptotic activity. A 20-fold increase of apoptotic activity was achieved from screening hit 3a to 5-methyl-3-phenyl-indole-2-carboxylic acid (4-methylbenzylidene)-hydrazide (9a) and 5-chloro-3-phenyl-indole-2-carboxylic acid (4-nitrobenzylidene)-hydrazide (9b), with EC50 value of 0.1 muM in the caspase activation assay in T47D breast cancer cells. Compound 9b also was found to be highly active in a standard growth inhibition assay with a GI(50) value of 0.9 muM in T47D cells. Compound 3a and its analogs were found to inhibit tubulin polymerization, which is the most probable primary mechanism of action of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.017

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。
• Design and synthesis of novel thiopheno-4-thiazolidinylindoles as potent antioxidant and antimicrobial agents
  作者：Jaiprakash Biradar、Parveen Rajesab、B. Sasidhar

  DOI：10.2478/s11696-013-0452-3

  日期：2014.1.1

  obtaining biologically active compounds. 3,5-disubstituted indol-2-carboxyhydrazides (Ia-If) were allowed to react with 3-acetyl-2,5-dichlorothiophene (II) to yield the corresponding 3,5-disubstituted indol-2-carbohydrazides (IIIa-IIIf). The pre-formed indolecarbohydrazides (IIIa-IIIf) were allowed to react with 2-mercaptoacetic acid or 2-mercaptopropanoic acid to produce thiopheno-4-thiazolidinylindoles

  为了获得具有生物活性的化合物，提出了一种新颖且方便的噻吩-4-噻唑啉基吲哚类似物的合成方法（IVa-IVi）。使3,5-二取代的吲哚-2-羧酰肼（Ia-If）与3-乙酰基-2,5-二氯噻吩（II）反应，生成相应的3,5-二取代的吲哚-2-碳酰肼（IIIa-IIIf））。使预先形成的吲哚碳酰肼（IIIa-IIIf）与2-巯基乙酸或2-巯基丙酸反应，生成噻吩-4-噻唑啉基吲哚（IVa-IVi）。该反应方案提供了简单，环保，无害，易于制备和高收率的特点。评价了合成化合物的抗氧化剂（清除自由基，总抗氧化剂能力和还原铁的抗氧化剂能力）和抗菌活性。产物的结构和纯度由它们的IR，1 H NMR，13 C NMR以及质谱和分析数据证实。所测试的大多数化合物都表现出非常重要的清除，抗氧化剂和抗菌活性。在吲哚的第五位上含有电子供体基团（CH 3）的化合物表现出优异的三价铁还原活性。本研究表明化合物IIIa-I
• Synthesis, spectroscopic characterization, and biological screening of binuclear transition metal complexes of bicompartmental Schiff bases containing indole and resorcinol moieties
  作者：Mahendra Raj KAREKAL、Mruthyunjayaswamy BENNIKALLU HIRE MATHADA

  DOI：10.3906/kim-1303-28

  日期：——

  UV-Vis, ESR, thermal studies, magnetic susceptibility, molar conductance, and powder-XRD data. All the complexes were binuclear and monomeric in nature. Cu(II) complexes have octahedral geometry, whereas Ni(II) and Zn(II) complexes have square planar and tetrahedral geometry, respectively. The redox property of the Cu(II) complex was investigated by electrochemical method using cyclic voltammetry.

  制备了一系列双室配体与ONO供体的双核Cu（II），Ni（II）和Zn（II）配合物。通过5-取代的-3-苯基-1H-吲哚-2-羧基酰肼与4，6-二乙酰基间苯二酚的缩合合成配体。通过元素分析和各种光谱研究（例如IR，1H NMR，ESI质量，UV-Vis，ESR，热研究，磁化率，摩尔电导和粉末XRD数据）对新合成的配体及其配合物进行了表征。所有的复合物本质上都是双核的和单体的。Cu（II）配合物具有八面体几何形状，而Ni（II）和Zn（II）配合物分别具有方形平面和四面体几何形状。采用循环伏安法通过电化学方法研究了Cu（II）配合物的氧化还原性质。为了评估金属离子对螯合的影响，通过最小抑菌浓度（MIC）方法筛选了配体及其金属配合物的抗菌和抗真菌活性。通过琼脂糖凝胶电泳分析所有复合物的DNA切割能力。
• New N′-alkylidene/cycloalkylidene derivatives of 5-methyl-3-phenyl-1H-indole-2-carbohydrazide: synthesis, crystal structure, and quantum mechanical calculations
  作者：F. Betül Kaynak、Devrim Öztürk、Süheyla Özbey、Gültaze Çapan

  DOI：10.1016/j.molstruc.2005.01.058

  日期：2005.4

  Abstract The condensation products of 5-methyl-3-phenyl-1H-indole-2-carbohydrazide (1) with 2-butanone, 3-pentanone and cyclopentanone were prepared. The adducts (2a-c) were characterized by microanalysis, UV, IR, 1H NMR, 13C NMR and EI mass spectrometry. 1H NMR spectra of 2a and 2b revealed rotational restriction about the C–N bond in solution (DMSO-d6) and displayed double resonances associated with

  摘要 制备了5-甲基-3-苯基-1H-吲哚-2-碳酰肼(1)与2-丁酮、3-戊酮和环戊酮的缩合产物。加合物 (2a-c) 通过微量分析、UV、IR、1H NMR、13C NMR 和 EI 质谱进行表征。2a 和 2b 的 1H NMR 谱揭示了溶液 (DMSO-d6) 中 C-N 键的旋转限制，并显示出与亚烷基部分的 CH3 和 CH2CH3 残基相关的双共振。在 2a 上运行可变温度 1H NMR 实验以克服旋转障碍，从而确定聚结温度，但在高达 77°C 时未观察到聚结。2a 和 2c 的结构分析也通过单晶 X 射线衍射进行，并通过理论计算证实（半经验 PM3 和 ab initio RHF/6-31G(d)）。
• In silico, in vitro and docking exploration for some novel coordination complexes derived from bioactive indole moiety
  作者：Nagesh Gunavanthrao Yernale、Basavarajaiah Suliphuldevara Mathada、Giridhar Baburao、Sushmita Sahane、Pooja Patil、Prashantha Karunakar、Adavala Venkatesulu

  DOI：10.1016/j.molstruc.2023.136512

  日期：2023.12

  ADME calculations were also performed to correlate and interpret the experimental results. The biological activity study illustrated enhancement in the activity of the free ligand containing bioactive indole moiety upon complex formation. The newly prepared Cu(II) and Zn(II) coordination complexes may be considered a promising antibacterial and antifungal agent. The Cu(II) and Zn(II) complexes showed MIC

  5-甲基-3-苯基-1H-吲哚-2-碳酰肼与4-甲氧基苯甲醛反应得到新的配体分子；N'-(4-甲氧基亚苄基)-5-甲基-3-苯基-1H-吲哚-2-碳酰肼。新型Cu(II)、Co(II)和Zn(II)配位化合物已成功制备。通过分析、FT-IR、 1 H NMR、质量、紫外-可见、摩尔电导率和磁化率测量对新制备的配体及其配位化合物进行了表征。光谱数据揭示了所有金属 (II) 配合物的八面体几何形状。通过6-31G ++在 DFT/B3LYP 水平上对配体进行 DFT 估计(d, p) 复制结构和几何形状。此外，还进行了分子对接和 ADME 计算来关联和解释实验结果。生物活性研究表明，在复合物形成后，含有生物活性吲哚部分的游离配体的活性增强。新制备的 Cu(II) 和 Zn(II) 配位配合物可能被认为是一种有前途的抗菌和抗真菌剂。Cu(II)和Zn(II)复合物对大肠杆菌、金黄色葡萄球菌和尖孢梭菌的MIC为12