2-羟基-3-甲基亚苯基肼 | 30991-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-3-甲基亚苯基肼
• 中文别名: 2-羟基-3-甲基苯甲酰肼
• 英文名称: 2-hydroxy-3-methyl benzohydrazide
• 英文别名: 2-hydroxy-3-methylbenzhydrazide；2-hydroxy-3-methylbenzohydrazide
• CAS: 30991-42-5
• 化学式: C₈H₁₀N₂O₂
• mdl: MFCD00017052
• 分子量: 166.18
• InChiKey: UWNTVIWGDXKENJ-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191°C
• 密度：
  1.262±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果遵照规格使用和储存，则不会分解，也未有已知危险反应。避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其存放在阴凉、干燥处。确保工作间有良好的通风或排气装置。

反应信息

• 作为反应物：
  描述：

  2-羟基-3-甲基亚苯基肼 在 sodium ethanolate 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-Methyl-6-(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：

  3-甲基水杨酸 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-羟基-3-甲基亚苯基肼
  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

文献信息

• Potential anticonvulsants. IX. Some isatin hydrazones and related compounds
  作者：Frank D. Popp

  DOI：10.1002/jhet.5570210614

  日期：1984.11

  A number of hydrazines, hydrazides, and related compounds have been condensed with isatin and substituted isatins. The anticonvulsant activity of these compounds is reported.

  许多肼，酰肼和相关化合物已与Isatin和取代的Isatin缩合。报道了这些化合物的抗惊厥活性。
• PENAM DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  申请人：TenNor Therapeutics Limited

  公开号：US20210070774A1

  公开（公告）日：2021-03-11

  Novel iron chelating group conjugated penam derivatives described herein show antibacterial activity, and could be used as antibacterial agents or beta-lactamase inhibitors (BLIs) which are of value for application in combination with other antibacterial agents.

  本文描述的新型铁螯合基团共轭的青霉素衍生物表现出抗菌活性，可用作抗菌剂或β-内酰胺酶抑制剂（BLIs），与其他抗菌剂联合应用具有价值。
• Synthesis and antiproliferative activity of some 5-substituted 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles
  作者：Joanna Matysiak、Anna Nasulewicz、Marzena Pełczyńska、Marta Świtalska、Iwona Jaroszewicz、Adam Opolski

  DOI：10.1016/j.ejmech.2005.12.007

  日期：2006.4

  antiproliferative activity against the cells of human cancer lines for 2-(2,4-dihydroxyphenyl)-5-(4-methoxybenzyloxy)-1,3,4-thiadiazole was found with ID(50) values comparable (HCV29T and SW707) or significantly lower (T47D) than for cisplatin applied as the reference compound. The influence of 5-substiution type of 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles on antiproliferative activity is discussed.

  合成了一系列新的5-取代的2-（2,4-二羟基苯基）-1,3,4-噻二唑，并对其抗增殖活性进行了评估。该化合物是通过亚磺酰基双（2,4-二羟基硫代苯甲酰基）（STB）与酰肼或氨基甲酸酯反应制备的。组取代包括烷基，烷氧基，芳基和杂芳基衍生物。化合物的结构由元素，IR，（1）H NMR和MS光谱分析确定。发现2-（2,4-二羟基苯基）-5-（4-甲氧基苄氧基）-1,3,4-噻二唑对人类癌细胞系具有最高的抗增殖活性，其ID（50）值可与HCV29T和SW707媲美）或（T47D）显着低于用作参考化合物的顺铂。5-取代类型的2-（2,4-二羟基苯基）-1,3的影响
• Relationship Between the structure of Newly Synthesized derivatives of 1,3,4-oxadiazole Containing 2-Methylphenol and their Antioxidant and Antibacterial Activities
  作者：Shaimaa Abed Saoud、Khalid Fahad Ali、Raied Mustafa Shakir

  DOI：10.13005/ojc/330423

  日期：2017.8.28

  1,3,4-oxadiazole-5-thion ring (2) successfully formed at position six of 2-methylphenol and five of their thioalkyl (3a-e). Furthermore 6-(5-(Aryl)-1,3,4-oxadiazol-2-yl)-2-methylphenol (5a-i) were formed at position six by two method. The first method was from cyclization their corresponding hydrazones (4a-e) of 2-hydroxy-3-methylbenzohydrazide (1) using bromine in glacial acetic acid. The second method was from cyclization the hydrazide with aryl carboxylic acid in the presence of phosphorusoxy chloride. The newly synthesized compounds were characterized from their IR, NMR and mass spectra. The antioxidant properties of these compounds were screened by 2,2-Diphenyl-1-picrylhydrazide (DPPH) and ferric reducing antioxidant power (FRAP) assays. Compound (4d) and (5h) exhibited significant antioxidant properties in both assays, compared to ascorbic acid, while compound (4e) exhibited slightly less antioxidant properties than ascorbic acid. Antibacterial activity was tested for the twenty one compounds against eight microorganisms (gram negative and gram positive). Compound (4d) and (5d) exhibited significant antibacterial activities compared to Amoxicillin and Kanamycin as antibiotic standards.

  1,3,4-噁二唑-5-硫环（2）成功地在2-甲基苯酚的第六位和五种其硫烷基衍生物（3a-e）中形成。此外，通过两种方法在第六位合成了6-(5-(芳基)-1,3,4-噁二唑-2-基)-2-甲基苯酚（5a-i）。第一种方法是使用冰醋酸中的溴化物对2-羟基-3-甲基苯肼（1）的相应肼化合物（4a-e）进行环化。第二种方法是将肼与芳香酸在磷氧化氯的存在下进行环化。新合成的化合物通过其红外光谱（IR）、核磁共振（NMR）和质谱（MS）进行表征。这些化合物的抗氧化性能通过2,2-二苯基-1-皮克里尔肼（DPPH）和铁还原抗氧化能力（FRAP）测定进行筛选。与抗坏血酸相比，化合物（4d）和（5h）在这两种测定中表现出显著的抗氧化特性，而化合物（4e）的抗氧化特性则略低于抗坏血酸。对21种化合物针对8种微生物（阴性革兰氏菌和阳性革兰氏菌）进行了抗菌活性测试。与抗生素标准阿莫西林和庆大霉素相比，化合物（4d）和（5d）表现出显著的抗菌活性。
• Acyl hydrazides and triazoles as novel inhibitors of mammalian cathepsin B and cathepsin H
  作者：Neera Raghav、Mamta Singh

  DOI：10.1016/j.ejmech.2014.03.007

  日期：2014.4

  determination of inhibition type and Ki values on purified cathepsin B and cathepsin H. The maximum inhibitory effect was exerted by 3-(3′-nitrophenyl)-5-(3′-nitrophenyl)-4-amino-1,2,4-triazoles (2c), 3-(4′-chlorophenyl)-5-(4′-chloro phenyl)-4-amino-1,2,4-triazoles (2h), 3-(3′-aminophenyl)-5-(3′-aminophenyl)-4-amino-1,2,4-triazoles (2i) and 4-methoxybenzohydrazide (1b).

  在过去的十年中，鉴定小分子量化合物作为半胱氨酸蛋白酶抑制剂的工作已成为焦点。在这个方向上，我们在这里介绍了一些酰基酰肼和三唑的简便微波辅助合成方法，随后将它们评估为蛋白酶抑制剂，并对两种重要的溶酶体半胱氨酸蛋白酶组织蛋白酶B和组织蛋白酶H进行了抑制研究。化合物通过1 H NMR，13 C NMR，质量和IR光谱数据表征。在pH 5.0的肝脏匀浆中发现对内源性蛋白水解具有抑制作用的化合物，需要进一步研究以确定其抑制类型和K i值。对纯化的组织蛋白酶B和组织蛋白酶H具有最大的抑制作用。3-（3'-硝基苯基）-5-（3'-硝基苯基）-4-氨基-1,2,4-三唑（2c），3发挥最大的抑制作用。-（4'-氯苯基）-5-（4'-氯苯基）-4-氨基-1,2,4-三唑（2h），3-（3'-氨基苯基）-5-（3'-氨基苯基） -4-氨基-1,2,4-三唑（2i）和4-甲氧基苯并肼（1b）。

表征谱图