3,5-二甲氧基苯甲酰肼 | 51707-38-1

• 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: 3,5-二甲氧基苯甲酰肼
• 中文别名: 3,5-二甲氧基苄肼；3,5-二甲氧基苯甲酸,肼
• 英文名称: 3,5-dimethoxy-benzoic acid hydrazide
• 英文别名: 3,5-dimethoxybenzohydrazide；3,5-dimethoxybenzhydrazide
• CAS: 51707-38-1
• 化学式: C₉H₁₂N₂O₃
• mdl: MFCD00017062
• 分子量: 196.206
• InChiKey: DOWVACHORBOSEF-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144°C
• 密度：
  1.189±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥处。确保工作间有良好的通风或排气设施。

反应信息

• 作为反应物：
  描述：

  3,5-二甲氧基苯甲酰肼 在 盐酸 、 sodium hydroxide 、 tetrafluoroboric acid 、 lithium 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 生成 橄榄醇二甲基醚
  参考文献：
  名称：

  Durrani, Aziz A.; Tyman, John H. P., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1658 - 1666

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 sodium hydroxide 、 肼 作用下， 以 水 为溶剂， 生成 3,5-二甲氧基苯甲酰肼
  参考文献：
  名称：

  3,5,2′,4′-Tetrahydroxychalcone, a new non-purine xanthine oxidase inhibitor

  摘要：

  Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid and the overproduction of uric acid will lead to hyperuricemia which is an important cause of gout. In the present study, three chalcone derivatives were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro. Of the compounds, only Compound 1, 3,5,2',4'-tetrahydroxychalcone, exhibited a significant inhibitory activity on xanthine oxidase with an IC50 value of 22.5 mu M. Lineweaver-Burk transformation of the inhibition kinetics data demonstrated that it was a competitive inhibitor of xanthine oxidase and Ki value was 17.4 mu M. In vivo, intragastric administration of Compound 1 was able to significantly reduce serum uric acid levels and inhibited hepatic xanthine oxidase activities of hyperuricemic mice in a dose-dependent manner. Acute toxicity study in mice showed that Compound 1 was very safe at a dose of up to 5 g/kg. These results suggest that Compound 1 is a novel competitive xanthine oxidase inhibitor and is worthy of further development. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2010.12.004

文献信息

• Synthesis and Cytotoxic Evaluation of Novel N-Methyl-4-phenoxypicolinamide Derivatives
  作者：Wei Li、Xin Zhai、Lu Ding、Limin Sun、Xiaomei Chen、Ping Gong、Tiemin Sun

  DOI：10.3390/molecules16065130

  日期：——

  A series of N-methyl-4-phenoxypicolinamide derivatives were synthesized and evaluated in vitro for their cytotoxic activity against A549, H460 and HT29 cell lines. Pharmacological data indicated that some of the target compounds possessed marked antiproliferative activity, superior to that of the reference drug sorafenib. As the most promising compound, 8e exhibited potent cytotoxicity with the IC50 value of 3.6, 1.7 and 3.0 μM against A549, H460 and HT-29 cell lines, respectively.

  一系列N-甲基-4-苯氧吡啶酰胺衍生物被合成并在体外对其对A549、H460和HT29细胞系的细胞毒活性进行了评估。药理学数据显示，一些目标化合物具有显著的抗增殖活性，优于参考药物索拉非尼。作为最有希望的化合物，8e表现出强大的细胞毒性，对A549、H460和HT29细胞系的IC50值分别为3.6、1.7和3.0 μM。
• Synthesis, antimicrobial evaluation and QSAR studies of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides
  作者：Davinder Kumar、Archana Kapoor、Ananda Thangadurai、Pradeep Kumar、Balasubramanian Narasimhan

  DOI：10.1016/j.cclet.2011.06.014

  日期：2011.11

  Abstract A series of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides ( 1 – 20 ) was synthesized and tested for in vitro antimicrobial activity. The results of antimicrobial studies indicated that the compounds having dinitro, methoxy, hydroxy and nitro substituents on phenyl ring of the aromatic acids were most active ones. The QSAR investigation indicated the importance of the topological

  摘要合成了一系列3-乙氧基-4-羟基亚苄基/ 4-硝基亚苄基酰肼（1 – 20），并测试了其体外抗菌活性。抗菌研究的结果表明，在芳族酸的苯环上具有二硝基，甲氧基，羟基和硝基取代基的化合物是活性最高的化合物。QSAR研究表明，拓扑参数，三阶分子连接性指数（3χ）在描述合成酰肼的抗菌活性方面具有重要意义。
• Design, synthesis, biological evaluation, and 3D-QSAR analysis of podophyllotoxin-dioxazole combination as tubulin targeting anticancer agents
  作者：Zi-Zhen Wang、Wen-Xue Sun、Xue Wang、Ya-Han Zhang、Han-Yue Qiu、Jin-Liang Qi、Yan-Jun Pang、Gui-Hua Lu、Xiao-Ming Wang、Fu-Gen Yu、Yong-Hua Yang

  DOI：10.1111/cbdd.12942

  日期：2017.8

  and high-throughput screening. To obtain new molecules for inhibiting tubulin, podophyllotoxin was adopted as the leading compound and 1,3,4-oxadiazole was brought in to the C-4 site of podophyllotoxin in this research. A series of seventeen podophyllotoxin derived esters have been achieved and then evaluated their antitumor activities against four different cancer cell lines: A549, MCF-7, HepG2 and HeLa

  抗癌药的发展从来不是一个简单的线性过程。那些药物设计专家在通过创造性的药物设计和高通量筛选未能找到理想的产品后，便开始从大自然中寻找灵感。为了获得抑制微管蛋白的新分子，以鬼臼毒素为主导化合物，并将1,3,4-恶二唑引入鬼臼毒素的C-4位点。已获得一系列十七种鬼臼毒素衍生的酯，然后评估了它们对四种不同癌细胞系（A549，MCF-7，HepG2和HeLa）的抗肿瘤活性。在所有化合物中，化合物7c对MCF-7癌细胞显示出最佳的抗增殖特性，IC50 = 2.54 +/- 0.82μM。显然，MCF-7中ROS的含量以一定的剂量增加。时间和剂量依赖性的细胞周期测定表明，化合物7c可以明显阻滞G2 / M期的细胞周期，以及CyclinA2和CDK2蛋白的上调。根据进一步的研究，共聚焦显微镜实验已证明化合物7c可通过阻止微管的聚合来抑制癌症的生长。同时，化合物7c可以理想地与微管蛋白的秋水仙碱位点整合。
• Synthesis, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents
  作者：Kai Liu、Xiang Lu、Hong-Jia Zhang、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2011.11.015

  日期：2012.1

  A series of 2-(benzylthio)-5-aryloxadiazole derivatives have been designed and synthesized, and their biological activities are also evaluated for EGFR inhibitory activity. Fourteen compounds among the twenty compounds are reported for the first time. Their chemical structures are characterized by 1H NMR, MS, and elemental analysis. Anti-proliferative and EGFR inhibition assay results have demonstrated

  已经设计和合成了一系列2-（苄硫基）-5-芳基恶二唑衍生物，并且还评估了它们的生物活性对EGFR的抑制活性。首次报道了二十种化合物中的十四种化合物。它们的化学结构通过1 H NMR，MS和元素分析进行表征。抗增殖和EGFR抑制测定的结果已经证实，化合物3e中示出了最有效的生物活性（IC 50  = 1.09μM为MCF-7和IC 50  = 1.51μM为EGFR）。已执行对接仿真以定位化合物3e进入EGFR活性位点以确定可能的结合模型，估计结合自由能值为-10.7 kcal / mol。在肿瘤生长抑制中具有有效抑制活性的化合物3e可能是有前途的抗肿瘤主导化合物，值得进一步研究。
• Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides
  作者：Shimin Xie、Lebin Su、Min Mo、Wang Zhou、Yongbo Zhou、Jianyu Dong

  DOI：10.1021/acs.joc.0c02328

  日期：2021.1.1

  coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivatives and the products. The reaction produces various thioesters in good to excellent yields with good functional group tolerance. In the reaction, stable and easily available aroylhydrazides are used as acyl sources and the

  通过易得的芳酰肼与二硫化物的铜催化的氧化偶联，开发了另一种硫酯化反应，其中N 2的氧化排出克服了羧酸衍生物和产物之间的活化障碍。该反应以良好的收率和优异的官能度耐受性产生了各种硫酯。在该反应中，将稳定且容易获得的芳酰基酰肼用作酰基源，并将相对无味的二硫化物用作S源。机理研究表明，铜盐与氧化剂（NH 4）2 S 2 O 8的反应 可以实现串联过程，包括去质子化，自由基介导的脱氮和CS键形成。