2-oxo-N-(m-tolyl)propanehydrazonoyl chloride | 77722-20-4

• 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-oxo-N-(m-tolyl)propanehydrazonoyl chloride
• 英文别名: 1-Chloro-1-[(3-methylphenyl)hydrazono]-2-propanone；N-(3-methylphenyl)-2-oxopropanehydrazonoyl chloride
• CAS: 77722-20-4
• 化学式: C₁₀H₁₁ClN₂O
• mdl: MFCD01220664
• 分子量: 210.663
• InChiKey: GNRUGHRKUSMOBX-UHFFFAOYSA-N

物化性质

• 沸点：
  306.7±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-N-(m-tolyl)propanehydrazonoyl chloride 以 乙醇 为溶剂， 反应 5.33h， 生成 N-[5-acetyl-3-(3-methylphenyl)-1,3,4-thiadiazol-2-ylidene]acetamide
  参考文献：
  名称：

  Eweiss, N.F.; Osman, A., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1713 - 1717

  摘要：

  DOI：

文献信息

• Synthesis of novel 1,2,4-triazoles and triazolo-thiadiazines as anticancer agents
  作者：Thoraya Abd El-Reheem FARGHALY、Magda Ahmad ABDALLAH、Huda Kamel MAHMOUD

  DOI：10.3906/kim-1504-13

  日期：——

  A new series of 7-arylazo-5$H$-3-(trifluoromethyl)-6-methyl-1,2,4-triazolo-[3,4-$b$]-1,3,4-thiadiazines was prepared by reaction of 4-amino-3-trifluoromethyl-5-mercapto-1,2,4-triazoles with $N$-aryl-2-oxo-propane hydrazonoyl chloride in dioxane under reflux in the presence of triethylamine. Furthermore, Schiff bases of 4-amino-5-mercapto-1,2,4-triazole derivatives were reacted with a variety of hydrazonoyl chlorides and gave the respective hydrazonothioates. In addition, the novel \textitbis}-(1,2,4-triazole-3-thione) was reacted with the appropriate hydrazonoyl chloride in dioxane under reflux in the presence of triethylamine to give the corresponding \textitbis}-(1,2,4-triazolethiohydrazonoate). The structures of the new compounds were established based on elemental and spectral data. The mechanism of the studied reaction was also discussed. Moreover, some of the new products were screened for their anticancer activity and the results obtained are promising and indicate that compounds \textbf4a }and \textbf4i} are the most active inhibitors against HEPG-2 and compounds \textbf4a} and \textbf13b} are active against HCT cell lines.

  一系列新的7-芳基偶氮-5$H$-3-(三氟甲基)-6-甲基-1,2,4-噻二唑-[3,4-$b$]-1,3,4-噻二唑被合成，反应物为4-氨基-3-三氟甲基-5-巯基-1,2,4-噻二唑与$N$-芳基-2-氧基丙烷氮酰氯，在有三乙胺存在的二噁烷中加热回流。此外，4-氨基-5-巯基-1,2,4-噻二唑衍生物的席夫碱与多种氮酰氯反应，生成相应的氮酰硫酸酯。此外，新型的\textitbis}-(1,2,4-噻二唑-3-硫酮)与适当的氮酰氯在有三乙胺存在的二噁烷中加热回流反应，生成相应的\textitbis}-(1,2,4-噻二唑硫氮酰盐)。新化合物的结构是基于元素分析和光谱数据确立的。还讨论了所研究反应的机制。此外，其中一些新产品进行了抗癌活性筛选，结果显示令人鼓舞，表明化合物\textbf4a}和\textbf4i}对HEPG-2细胞的抑制活性最强，而化合物\textbf4a}和\textbf13b}对HCT细胞系也具有活性。
• Microwaves assisted synthesis of antitumor agents of novel azoles, azines, and azoloazines pendant to phenyl sulfone moiety and molecular docking for VEGFR-2 kinase
  作者：Mohamed R. Shaaban、Thoraya A. Farghaly、Amani M.R. Alsaedi、Hanan Gaber Abdulwahab

  DOI：10.1016/j.molstruc.2021.131657

  日期：2022.2

  phenylsulfone-enaminones which were synthesized in short reaction time with excellent yield under microwaves irradiation. These two enaminones were reacted with both nucleophiles and electrophiles to afford novel heterocycles bearing phenylsulfone moiety. The structure of all prepared phenylsulfone derivatives as well as their mechanistic pathways were studied based on their spectral data. Moreover, seventeen

  本研究文章包含两种有价值的起始苯砜 - 烯胺酮，它们在微波辐射下在短时间内以优异的收率合成。这两种烯胺酮与亲核试剂和亲电试剂反应，得到带有苯砜部分的新型杂环。基于它们的光谱数据研究了所有制备的苯砜衍生物的结构及其机理途径。此外，在体外筛选了17 种苯砜衍生物对 HepG-2 和 HCT-116 细胞系的抗癌活性。化合物 5 和 7 与阿霉素对 HepG-2 细胞系具有同等效力。此外，二苯砜衍生物 5 对人结肠癌细胞系的效力是阿霉素的 3 倍，IC 50 = 3.9 和 9.4 μg/mL，分别。值得注意的是，化合物 10 对两种测试细胞系的活性是阿霉素的 2 倍。还进行了标题化合物与 VEGFR-2 激酶的对接研究。
• Synthesis, Characterization, and Anticancer Screening of Some New Bithiazole Derivatives
  作者：N. A. Abdel Latif、E. M. H. Abbas、T. A. Farghaly、H. M. Awad

  DOI：10.1134/s1070428020060202

  日期：2020.6

  condensation of 2-2-[(1-arylethylidene)hydrazinylidene]thiazolidin-4-ylidene}hydrazine-1-carbothioamides with halo ketones, halo esters, and α-keto hydrazonoyl halides. The structures of all prepared compounds were proposed on the basis of their IR,1H and 13C NMR, and mass spectra. All the synthesized compounds were screened for their cytotoxicity against three human cancer cell lines, HCT-116 (human colorectal

  摘要通过将2- 2-[（（1-芳基亚乙基）肼基]噻唑烷丁-4-亚基}肼-1-碳硫酰胺与卤代酮，卤代酯和α-酮基卤代甲酰卤缩合，合成了二十种新的噻唑衍生物。根据所有化合物的IR，1 H和13 C NMR和质谱图，提出了所有化合物的结构。筛选所有合成的化合物对三种人类癌细胞系HCT-116（人类结直肠癌），MCF-7（人类乳腺腺癌）和HepG2（人类肝细胞癌）的细胞毒性。两种化合物（12d和12b）对HCT-116人结肠直肠癌细胞具有显着更强的抗癌活性。对于MCF-7人乳腺癌细胞，三种化合物（12b，4b和4a）的效力明显强于参考药物阿霉素。九种合成化合物（8a，7a，9b，12d，12c，7b，10a，5a和12b）显示出比阿霉素对HepG2人肝癌细胞具有显着更高的活性。
• Microwave-assisted and thermal synthesis of nanosized thiazolyl-phenothiazine derivatives and their biological activities
  作者：Manal M. Alsharekh、Ismail I. Althagafi、Mohamed R. Shaaban、Thoraya A. Farghaly

  DOI：10.1007/s11164-018-3594-7

  日期：2019.2

  Efficient synthesis of a series of nanosized phenothiazine derivatives incorporating thiazole moiety was achieved using microwave irradiation as well as thermal conditions. Reaction of 2-(1-(10H-phenothiazin-2-yl)ethylidene)hydrazine-1-carbothioamide with various types of hydrazonoyl halide or α-haloketone afforded corresponding thiazolyl phenothiazines in good to excellent yield. Mass, 1H and 13C

  使用微波辐射以及热条件，可以高效合成一系列结合噻唑部分的纳米吩噻嗪衍生物。2-（1-（10 H-吩噻嗪-2-基）亚乙基）肼-1-碳硫酰胺与各种类型的酰肼基卤化物或α-卤代酮的反应以良好或优异的产率提供了相应的噻唑基吩噻嗪。质量，1 H和13C核磁共振（NMR），紫外-可见（UV-Vis），X射线衍射（XRD）和元素分析证实了所有新衍生物的结构。与常规方法相比，该反应在微波辐射下以更短的反应时间进行且产率更高。研究了选定衍生物的抗微生物和抗肿瘤活性，发现其中一些衍生物与标准参照物相比具有很高的效力。
• Synthesis and DNA binding of novel bioactive thiazole derivatives pendent to N-phenylmorpholine moiety
  作者：Thoraya A. Farghaly、Alaa M. Abo Alnaja、Hoda A. El-Ghamry、Mohamed R. Shaaban

  DOI：10.1016/j.bioorg.2020.104103

  日期：2020.9

  An easy access to a series of N-phenylmorpholine derivatives linked with thiazole or formazan moieties were achieved using simple experimental procedure under conventional and microwaves irradiation conditions. The reaction of 2-(N-phenylmorpholine)ethylidene)hydrazine-1-carbothioamide derivatives and [1-(4-morpholin-4-yl-phenyl)-ethylidene]-hydrazine with a variety of hydrazonoyl chlorides or phenacyl

  在常规和微波辐射条件下，使用简单的实验程序即可轻松获得一系列与噻唑或甲for部分相连的N-苯基吗啉衍生物。2-（N-苯基吗啉）亚乙基）肼-1-碳硫酰胺衍生物和[1-（4-吗啉-4-基-苯基）-亚乙基]肼与多种酰氯或苯甲酰溴衍生物反应，得到相应的噻唑或ñ链接到-substitutedhydrazino衍生物ñ-苯基吗啉部分具有良好至优异的产率。通过光谱和元素分析充分强调和表征了新合成化合物的结构。使用UV-Vis吸收和粘度测量评估了某些选定化合物与SS-DNA的结合方式。结果显示大多数测试化合物的插入结合模式。对于从合成衍生物中选择的某些化合物，已经研究了抗菌和抗癌活性。他们的结果表明，某些衍生物可同时抵抗微生物和癌细胞。