2-hydroxy-4-methylbenzohydrazide | 69443-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-4-methylbenzohydrazide
• 英文别名: 4-methylsalicyloylhydrazide；2-hydroxy-4-methylbenzohydrazine；2-hydroxy-4-methyl-benzoic acid hydrazide；2-Hydroxy-4-methyl-benzoesaeure-hydrazid
• CAS: 69443-64-7
• 化学式: C₈H₁₀N₂O₂
• mdl: MFCD09948889
• 分子量: 166.18
• InChiKey: CIPACNIYKFAUQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-methylbenzohydrazide 在 sodium ethanolate 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-Methyl-2-(5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazol-2-yl)phenol
  参考文献：
  名称：

  Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents

  摘要：

  A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 +/- 0.2, 30.0 +/- 1.2, 18.3 +/- 1.4 mu M, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 mu M, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 mu g/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.008
• 作为产物：
  描述：

  4-甲基水杨酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-hydroxy-4-methylbenzohydrazide
  参考文献：
  名称：

  新型2-（1,3,4-恶二唑-2-基硫基）-1-苯基乙酮衍生物的合成，生物学评价和分子对接研究

  摘要：

  在本研究中，合成了一系列新型的2-（1,3,4-恶二唑-2-基硫基）-1-苯基乙酮衍生物（6a - 6x）作为潜在的粘着斑激酶（FAK）抑制剂。生物测定表明，化合物6i表现出最强的活性，抑制了MCF-7和A431细胞系的生长，IC 50值分别为140±10 nM和10±1 nM。化合物6i还表现出显着的FAK抑制活性（IC 50  = 20±1 nM）。进行对接模拟以将化合物6i定位在FAK的活性位点中，以确定可能的结合模型。

  DOI：

  10.1016/j.bmc.2012.03.061

文献信息

• Synthesis, biological evaluation and molecular docking studies of novel 2-(1,3,4-oxadiazol-2-ylthio)-1-phenylethanone derivatives
  作者：Li-Rong Zhang、Zhi-Jun Liu、Hui Zhang、Jian Sun、Yin Luo、Ting-Ting Zhao、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.03.061

  日期：2012.6

  In present study, a series of new 2-(1,3,4-oxadiazol-2-ylthio)-1-phenylethanone derivatives (6a–6x) as potential focal adhesion kinase (FAK) inhibitors were synthesized. The bioassay assays demonstrated that compound 6i showed the most potent activity, which inhibited the growth of MCF-7 and A431 cell lines with IC50 values of 140 ± 10 nM and 10 ± 1 nM, respectively. Compound 6i also exhibited significant

  在本研究中，合成了一系列新型的2-（1,3,4-恶二唑-2-基硫基）-1-苯基乙酮衍生物（6a - 6x）作为潜在的粘着斑激酶（FAK）抑制剂。生物测定表明，化合物6i表现出最强的活性，抑制了MCF-7和A431细胞系的生长，IC 50值分别为140±10 nM和10±1 nM。化合物6i还表现出显着的FAK抑制活性（IC 50  = 20±1 nM）。进行对接模拟以将化合物6i定位在FAK的活性位点中，以确定可能的结合模型。
• Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents
  作者：Zhi-Ming Zhang、Xue-Wei Zhang、Zong-Zheng Zhao、Ru Yan、Rui Xu、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.03.064

  日期：2012.5

  synthesized for their potential immunosuppressive activity. Among them, compound 6z displayed the most potent biological activity against lymph node cells (inhibition = 38.76% for lymph node cells and IC50 = 0.31 μM for PI3Kγ). The preliminary mechanism of compound 6z inhibition effects was also detected by flow cytometry (FCM) and the compound exerted immunosuppressive activity via inducing the apoptosis

  由于其潜在的免疫抑制活性，首先合成了一系列衍生自4-甲氧基水杨酸或4-甲基水杨酸（6a - 6z）的1,3,4-恶二唑衍生物。其中，化合物6z对淋巴结细胞表现出最强的生物学活性（淋巴结细胞抑制率为38.76％ ，PI3Kγ的IC 50 = 0.31μM）。还通过流式细胞术（FCM）检测了化合物6z抑制作用的初步机理，并且该化合物通过以剂量依赖性方式诱导活化的淋巴结细胞的凋亡而发挥免疫抑制活性。进行对接仿真以定位化合物6z 进入PI3Kγ结构的活性位点，确定可能的结合模型。
• 含2-巯基苯乙酮的1,3,4-噁二唑衍生物及其 制法与抗肿瘤活性
  申请人：南京大学

  公开号：CN103319431B

  公开（公告）日：2017-04-26

  本发明公开了一类含2‑巯基苯乙酮的1,3,4‑噁二唑衍生物及其制备方法，其具有如下通式：式中R1为：；R2为：H或Br。该衍生物为潜在的抗肿瘤药物，对MCF‑7和A431具有抑制作用，对A431有强烈抑制作用。
• Synthesis, Characterization, and Crystal Structure of a Metallamacrocycle
  作者：Dingjun Zhang、Yuxian Chen、Qiang Zhao、Youzhi Wu

  DOI：10.1002/zaac.201000459

  日期：2011.7

  The novel macrocyclic decanuclear manganese(III) 30-metallacrown-10 compound [Mn10(RS-3-chmshz)10(DMF)10]·9DMF (1) was synthesized by self-assembly and characterized (H3RS-3-chmshz = N-((R,S)-3-cyclohexenoyl)-5-methylsalicylhydrazide). Compound 1 is a 30-membered decanuclear metallamacrocycle and crystallizes in triclinic space group P21/c, in an alternating …ΔΛΔΛ…-type chiral configuration. The decanuclear

  新型大环十核锰(III) 30-金属冠-10化合物[Mn10(RS-3-chmshz)10(DMF)10]·9DMF (1)通过自组装合成并表征(H3RS-3-chmshz = N -((R,S)-3-环己烯酰基)-5-甲基水杨酰肼)。化合物 1 是一个 30 元十核金属大环，在三斜空间群 P21/c 中结晶，呈交替的…ΔΛΔΛ…型手性构型。十核系统的直径约为 2.6 nm，厚度约为 1.1 nm。指向金属大环空腔的外消旋 N-(R,S)-3-环己烯酰基显示出替代的 R,S 手性构型。标题 30-metallacrown-10 化合物的磁性测量显示弱反铁磁交换相互作用。
• An 18-Membered Hexanuclear Manganese (MnN₂)₆ Metalladiazamacrocycle
  作者：Qi-Feng Liang

  DOI：10.1515/znb-2009-0701

  日期：2009.7.1

  The macrocyclic hexanuclear manganese(III) 18-metallacrown-6, [Mn₆(pmshz)₆(DMF)₄(C₂H₅- OH)₂]·4DMF (1), where pmshz³⁻ is N-propionyl-N'-5-methylsalicylhydrazide, has been synthesized by self-assembly and structurally characterized. The ring is formed by the succession of six structural moieties of the type [Mn(III)-N-N] with hydrazide N-N groups bridging the ring Mn ions. The ligand enforces the metal ions to form the stereochemistry of a configuration with alternate. . .ΔΛΔΛ. . .- type enantiomeric chiral units. The peripheral core ring is ~18.6 in diameter and ~12.4 Å in thickness. The title metallacrown exhibits photoluminescent properties in the solid state and a weak antiferromagnetic exchange interaction.

  由自组装合成并结构表征的大环六核锰(III) 18-金属冠醚-6，[Mn₆(pmshz)₆(DMF)₄(C₂H₅-OH)₂]·4DMF (1)，其中pmshz³⁻为N-丙酰-N'-5-甲基水杨酰肼。该环由六个[Mn(III)-N-N]类型的结构基元组成，肼N-N基团桥接环中的Mn离子。配体强制金属离子形成交替的ΔΛΔΛ...型对映手性单元的立体化学。外围的核心环直径约为18.6，厚度约为12.4 Å。标题金属冠醚在固态下表现出光致发光性质和弱反铁磁交换相互作用。