N'-(2-hydroxybenzylidene)-2-(1H-indole-3-yl)acetohydrazide | 354991-20-1

• 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'-(2-hydroxybenzylidene)-2-(1H-indole-3-yl)acetohydrazide
• 英文别名: N’-(2-hydroxybenzylidene)-2-(1H-indol-3-yl)acetohydrazide；N'-(2-hydroxybenzylidene)-2-(1h-indole-3-yl) acetohydrazide；N-[(2-hydroxyphenyl)methylideneamino]-2-(1H-indol-3-yl)acetamide
• CAS: 354991-20-1
• 化学式: C₁₇H₁₅N₃O₂
• mdl: MFCD00713116
• 分子量: 293.325
• InChiKey: FBWKZUXQSNCKMS-UHFFFAOYSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(2-hydroxybenzylidene)-2-(1H-indole-3-yl)acetohydrazide 在 lead(IV) tetraacetate 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

  摘要：

  First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spiro-cyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.077
• 作为产物：
  描述：

  甲基吲哚-3-乙酸盐 在 溶剂黄146 、 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 N'-(2-hydroxybenzylidene)-2-(1H-indole-3-yl)acetohydrazide
  参考文献：
  名称：

  Synthesis, in vitro lipoxygenase inhibition, docking study and thermal stability analyses of novel indole derivatives

  摘要：

  一系列吲哚衍生物已被合成并进行生物学评估，以鉴定出强效的新型脂氧合酶（LOX）抑制剂。所有选定的吲哚衍生物均经过LOX抑制研究筛选。大多数化合物显示出良好的体外LOX抑制性能，其IC50值范围为53.61 ± 0.14至198.61 ± 0.11 μM（平均值 ± 标准误差），相比之下，标准抑制剂黄芩素（baicalein）的IC50值为22.4 ± 1.3 μM。探讨了结构活性关系，并对最活跃的化合物4f进行了对接模拟。通过在氮气气氛下以20 °C min−1的加热速率进行热重分析和差示扫描量热分析，研究了吲哚衍生物的热稳定性和熔点。含有双苯基的化合物4f被发现是测试化合物中最强效的（IC50 53.61 ± 0.14 μM）和热稳定性最高的。亚胺（C=N）被发现是提高吲哚衍生物热稳定性的关键基团。通过傅里叶变换红外光谱（FT-IR）、核磁共振（NMR）和元素分析技术进行了结构表征。

  DOI：

  10.1007/s13738-013-0308-3

文献信息

• Synthesis, in vitro lipoxygenase inhibition, docking study and thermal stability analyses of novel indole derivatives
  作者：Muhammad Yar、Lala Rukh Sidra、Eleni Pontiki、Nafeesa Mushtaq、Muhammad Ashraf、Rumana Nasar、Islam Ullah Khan、Nasir Mahmood、Syed Ali Raza Naqvi、Zulfiqar Ali Khan、Sohail Anjum Shahzad

  DOI：10.1007/s13738-013-0308-3

  日期：2014.4

  A series of indole derivatives has been synthesized and biologically evaluated to identify potent new lipoxygenase (LOX) inhibitors. All selected indole derivatives were screened for their LOX inhibition studies. Most of compounds showed good in vitro LOX inhibition properties exhibiting IC50 values in the range of 53.61 ± 0.14 to 198.61 ± 0.11 μM (mean ± SEM), as compared to the standard inhibitor baicalein with IC50 value 22.4 ± 1.3 μM. Structure activity relationship has been discussed and docking stimulation of most active compound 4f has also performed. Thermal stability and melting point of indole derivatives have been performed by thermal gravimetric analysis and differential scanning calorimetry analysis under nitrogen atmosphere at heating rate of 20 °C min−1. Compound 4f bearing bis-phenyl moiety has been found to be the most potent (IC50 53.61 ± 0.14 μM) and thermally most stable among the tested compounds. Imine (C=N) was found to be the key moiety for increasing the thermal stabilities of indole derivatives. FT-IR, NMR and elemental analysis techniques were performed for structural characterization.

  一系列吲哚衍生物已被合成并进行生物学评估，以鉴定出强效的新型脂氧合酶（LOX）抑制剂。所有选定的吲哚衍生物均经过LOX抑制研究筛选。大多数化合物显示出良好的体外LOX抑制性能，其IC50值范围为53.61 ± 0.14至198.61 ± 0.11 μM（平均值 ± 标准误差），相比之下，标准抑制剂黄芩素（baicalein）的IC50值为22.4 ± 1.3 μM。探讨了结构活性关系，并对最活跃的化合物4f进行了对接模拟。通过在氮气气氛下以20 °C min−1的加热速率进行热重分析和差示扫描量热分析，研究了吲哚衍生物的热稳定性和熔点。含有双苯基的化合物4f被发现是测试化合物中最强效的（IC50 53.61 ± 0.14 μM）和热稳定性最高的。亚胺（C=N）被发现是提高吲哚衍生物热稳定性的关键基团。通过傅里叶变换红外光谱（FT-IR）、核磁共振（NMR）和元素分析技术进行了结构表征。
• Novel hydrazones
  申请人：——

  公开号：US20040110963A1

  公开（公告）日：2004-06-10

  The invention relates to novel hydrazone derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as anti-infectives.

  本发明涉及新型腙类衍生物及其在制备药物组合物的活性成分中的应用。本发明还涉及相关方面，包括制备该化合物的过程、含有该化合物中的一种或多种的药物组合物，尤其是它们作为抗感染剂的应用。
• 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.
• Chloromethylated polystyrene cross-linked with divinylbenzene and grafted with vanadium(IV) and vanadium(V) complexes having ONO donor ligand for the catalytic activity
  作者：Mannar R. Maurya、Naveen Kumar

  DOI：10.1016/j.molcata.2013.12.006

  日期：2014.3

  The ligand H(2)sal-iah (I), derived from salicylaldehyde and indole-3-acetic hydrazide, reacts with [(VO)-O-IV(acac)(2)] in methanol to give oxidovanadium(IV) complex [(VO)-O-IV(sal-iah)(H2O)] (1). In the presence of KOH, arial oxidation of 1 in methanol yields dioxidovanadium(V) complex K[(VO2)-O-V(sal-iah).H2O] (2). Complex 1 has been grafted via covalent bonding through imino nitrogen of the indole group to chloromethylated polystyrene cross-linked with 5% divinylbenzene now abbreviated as PS-[(VO)-O-V(sal-iah)(H2O)] (3)1. Its oxidomethoxido vanadium(V) analog PS-[(VO)-O-V(OMe)(sal-iah)] (4)} can be obtained by aerial oxidation of methanolic suspension of 3. All these complexes are characterized by various spectroscopic techniques (IR, electronic,H-1 and V-51 NMR, electron paramagnetic resonance (EPR) and thermal as well as field-emission scanning electron micrographs (FE-SEM)) studies. The EPR spectrum of 3 indicates that the magnetically dilute VIv0-centers are well dispersed in the polymer matrix while EPR spectrum of 1 shows slightly different binding mode around vanadium center. H-1 and V-51 NMR spectra of 2 are compatible with the existence of expected dioxide species as the major product and oxidomethoxido species as a minor component in solution. Independent of the species presents in methanol, complexes 1 and 2 upon treatment with H2O2 both change to same oxidoperoxido species. The polymer-grafted complex 4 catalyzes the oxidation, by H2O2, of styrene and cyclohexene. Under optimized reaction conditions, the oxidation of styrene gave 95% conversion where styrene oxide, benzaldehyde, benzoic acid, 1-phenylethane-1,2-diol and phenylacetaldehyde are products. Oxidation of cyclohexene gave 96% conversion with cyclohexene oxide, 2-cyclohexene-l-ol, cyclohexane-1,2-diol and 2-cyclohexene-1-one as the major products. Neat complex K[(VO2)-O-V(sal-iah)].H2O (2) is equally active but the recyclability and heterogeneity tests of polymer-grafted complex make it better over neat analog. (C) 2013 Elsevier B.V. All rights reserved.
• Polymer and non-polymer-grafted dioxidomolybdenum(VI) complexes having ONO donor ligand and their catalytic activities for the oxidative bromination of organic substrates
  作者：Mannar R. Maurya、Naveen Kumar、Fernando Avecilla

  DOI：10.1016/j.molcata.2014.05.002

  日期：2014.10

  The ligand H(2)sal-iah (I), derived from salicylaldehyde and indole-3-acetic hydrazide, reacts with [(MoO2)-O-VI(acac)(2)] in methanol to give dioxidomolybdenum(VI) complex [(MoO2)-O-VI(sal-iah)(MeOH)] (1). Drop wise addition of 30% aqueous H2O2 to the methanolic solution of 1 yields complex [(MoO)-O-VI(O-2)(sal-iah)(MeOH)] (2). Complex 1 has been grafted via covalent bonding through imino nitrogen of the indole to chloromethylated polystyrene cross-linked with 5% divinylbenzene now abbreviated as PS-[mo(VI)O(2)(sal-iah)(MeOH)] (3)}. All these complexes are characterized by various spectroscopic techniques (IR, electronic, H-1 and C-13 NMR) and thermal as well as field-emission scanning electron micrographs (FE-SEM) studies. The crystal structure of 1 has been determined, confirming the ONO binding mode of I. The polymer-grafted complex 3 catalyzes the oxidative bromination, by H2O2, of styrene and trans-stilbene. Under the optimized reaction conditions, the oxidative bromination of styrene gave 96% conversion in 2 h time where 2-bromo-1-phenylethane-1-ol and 1,2-dibromo-1-phenylethane are the main products and 1-phenylethane-1,2-diol is the product obtained by the attack of nucleophile water on the a-carbon of 2-bromo-1-phenylethane-1-ol. Oxidative bromination of trans-stilbene gave 96% conversion with 2,3-diphenyloxirane (trans-stilbene oxide), 1,2-dibromo-1,2-diphenylethane and 2-bromo-1,2-diphenylethanol as the products. Suitable reaction mechanisms for both reactions have been suggested. Neat complex [(MoO2)-O-VI(sal-iah)(MeOH)] (1) is equally active but the recyclability and heterogeneity tests of polymer-grafted complex makes it better over neat analog. (C) 2014 Elsevier B.V. All rights reserved.