N'-(1H-indol-3-ylmethylidene)pyridine-4-carbohydrazide | 10245-44-0

• 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
• 英文名称: N'-(1H-indol-3-ylmethylidene)pyridine-4-carbohydrazide
• 英文别名: N'-((1H-indol-3-yl)methylene)isonicotinohydrazide；indole-3-carbaldehyde isonicotinoylhydrazone；N-(1H-indol-3-ylmethylideneamino)pyridine-4-carboxamide
• CAS: 10245-44-0
• 化学式: C₁₅H₁₂N₄O
• mdl: MFCD00182115
• 分子量: 264.286
• InChiKey: YRXIZOPHHNNLIT-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  70.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N'-(1H-indol-3-ylmethylidene)pyridine-4-carbohydrazide 在 silica gel 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.12h， 生成 1-(2-(1H-indol-3-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)-3-(p-tolyl)prop-2-en-1-one
  参考文献：
  名称：

  一些新型的以吲哚和吡啶为基础的1,3,4-恶二唑衍生物作为潜在的抗结核药的合成，生物学评价和分子对接研究

  摘要：

  合成了一系列基于吲哚和吡啶的1,3,4-恶二唑衍生物5a - t，并评估了它们在活跃和休眠状态下对结核分枝杆菌H 37 Ra（MTB）和牛分枝杆菌BCG的体外抗结核活性。化合物5b，5e，5g和5q显示出非常好的抗结核活性。所有新合成的化合物5a – t使用改良的MTT分析法进一步评估了它们对HeLa，A549和PANC-1细胞系的抗增殖活性，发现无细胞毒性。基于针对牛分枝杆菌BCG的细胞毒性和MIC值，计算处于活性和休眠状态的大多数活性化合物5b，5e，5g和5q的选择性指数（SI）（SI = GI 50 / MIC）。化合物5b，5e和5g对所有三种细胞系的SI值均≤10，并且可以安全地进行提前筛查。化合物5a – t进一步筛选了它们对四种细菌菌株的抗菌活性，以评估其对MTB的选择性。此外，分子对接研究揭示了这些化合物在烯酰还原酶（InhA）活性位点的结合模式，进而有助于建立抑制分枝杆

  DOI：

  10.1016/j.bmcl.2016.02.043
• 作为产物：
  描述：

  异烟酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N'-(1H-indol-3-ylmethylidene)pyridine-4-carbohydrazide
  参考文献：
  名称：

  Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies

  摘要：

  DOI：

  10.1007/s00044-011-9662-9

文献信息

• Potential anticonvulsants. VIII. Some hydrazones of indole-3-carboxaldehyde
  作者：Frank D. Popp

  DOI：10.1002/jhet.5570210273

  日期：1984.3

  Indole-3-carboxaldehyde and some additional aldehydes were condensed with various hydrazines, hydrazides, and related compounds. A number of the products exhibited low levels of anticonvulsant activity.

  吲哚-3-羧醛和一些其他醛与各种肼，酰肼和相关化合物缩合。许多产品表现出低水平的抗惊厥活性。
• Synthesis and anticancer activity study of indolyl hydrazide–hydrazones
  作者：Swapna Sundaree、Buchi Reddy Vaddula、Mukund P. Tantak、Santosh B. Khandagale、Chun Shi、Kavita Shah、Dalip Kumar

  DOI：10.1007/s00044-016-1522-1

  日期：2016.5

  )methylene)hydrazides were synthesized and evaluated for their in vitro antiproliferative activities against various cancer cell lines. Formation of indole hydrazide–hydrazones was accomplished by the reaction of indole 3-carboxaldehyde with aryl/alkyl hydrazides in the presence of acetic acid. Out of synthesized twenty-two compounds, some of the analogs exhibited specificity toward breast (18b, 18d

  合成了一系列N '-（（（1-（取代）-1H-吲哚-3-基）亚甲基）酰肼，并评估了它们对各种癌细胞的体外抗增殖活性。吲哚酰肼-azo的形成是通过在乙酸存在下吲哚3-羧醛与芳基/烷基酰肼的反应来完成的。在合成的22种化合物中，某些类似物对乳腺癌（18b，18d，18f和18j）和前列腺癌（18t和18v）表现出特异性。在制备的衍生物中，化合物18b，18d和18j具有最大的细胞毒性（IC50  = 0.9、0.4和0.8 µM，分别针对已筛选的癌细胞系。PC3细胞暴露于18d或18j导致裂解的PARP1水平升高，表明吲哚基酰肼-酮诱导PC3细胞凋亡。
• Synthesis of Novel Indole Hydrazone Derivatives and Evaluation of Their Antiplatelet Aggregation Activity
  作者：Vida Mashayekhi、Kamaleddin Haj Mohammad Ebrahim Tehrani、Salimeh Amidi、Farzad Kobarfard

  DOI：10.1248/cpb.c12-00597

  日期：——

  Based on the existing reports regarding the antiplatelet aggregation activity of hydrazone derivatives, a series of indole hydrazone derivatives were considered as potential antiplatelet agents and synthesized. The structures of the synthesized compounds were confirmed by spectral data and elemental analysis. The new indole hydrazone derivatives were evaluated for their ability to inhibit platelet aggregation induced by adenosine diphosphate (ADP) and arachidonic acid (AA). Compounds 1h and 3h exhibited remarkable activity against arachidonic acid induced platelet aggregation with IC50 values comparable to that of indomethacin and compound 1i efficiently inhibited platelet aggregation induced by both ADP and AA.

  基于现有关于酰腙类化合物抗血小板聚集活性的报道，我们考虑合成一系列吲哚酰腙衍生物作为潜在的抗血小板药物。通过光谱数据和元素分析确认了合成化合物的结构。这些新型吲哚酰腙衍生物被评估了其抑制由二磷酸腺苷（ADP）和花生四烯酸（AA）诱导的血小板聚集的能力。化合物1h和3h对花生四烯酸诱导的血小板聚集表现出显著的抑制活性，其IC50值与吲哚美辛相当，而化合物1i则有效地抑制了由ADP和AA诱导的血小板聚集。
• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.
• Synthesis and antituberculosis activity of indole–pyridine derived hydrazides, hydrazide–hydrazones, and thiosemicarbazones
  作者：Valeriya Velezheva、Patrick Brennan、Pavel Ivanov、Albert Kornienko、Sergey Lyubimov、Konstantin Kazarian、Boris Nikonenko、Konstantin Majorov、Alexander Apt

  DOI：10.1016/j.bmcl.2015.12.049

  日期：2016.2

  We describe the design, synthesis, and in vitro antimycobacterial activity of a series of novel simple hybrid hydrazides and hydrazide-hydrazones combining indole and pyridine nuclei. The compounds are derivatives of 1-acetylindoxyl or substituted indole-3-carboxaldehydes tethered via a hydrazine group by simple CAN or double C=N bonds with 3-and 4-pyridines, 1-oxide 3-and 4-pyridine carbohydrazides. The most active of 15 compounds showed MICs values against an INH-sensitive strain of Mycobacterium tuberculosis H37Rv equal to that of INH (0.05-2 mu g/mL). Five compounds demonstrated appreciable activity against the INH-resistant M. tuberculosis CN-40 clinical isolate (MICs: 2-5 mu g/mL), providing justification for further in vivo studies. (C) 2015 Elsevier Ltd. All rights reserved.