N-(3-chlorophenyl)-2-oxo-propanehydrazonoyl chloride | 39250-16-3

• 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: N-(3-chlorophenyl)-2-oxo-propanehydrazonoyl chloride
• 英文别名: pyruvoyl chloride 1-[(m-chlorophenyl)hydrazone]；1-chloro-1-[(3-chlorophenyl) hydrazono]-2-propanone；N-(3-chlorophenyl)-2-oxopropanehydrazonoyl chloride
• CAS: 39250-16-3
• 化学式: C₉H₈Cl₂N₂O
• mdl: MFCD01220663
• 分子量: 231.081
• InChiKey: DRQRXNVIADUUCG-UHFFFAOYSA-N

物化性质

• 沸点：
  320.2±44.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  N-(3-chlorophenyl)-2-oxo-propanehydrazonoyl chloride 在 sodium azide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以92%的产率得到N-(3-chlorophenyl)-2-oxopropanehydrazonoyl azide
  参考文献：
  名称：

  串联酸促进分子内叠氮化物-腙电环化/水解方法合成N-氨基四唑

  摘要：

  完成了通过叠氮腙串联电环化/水解合成一系列以前未知的N- (杂芳基)-和N- (芳基)氨基四唑的通用方法。所描述的协议适用于广泛的目标N-取代氨基四唑，这些目标在平稳反应条件下以良好到高产率制备。重要的是，所提出的方法被认为是以良好和高产率获得 1,2,5-恶二唑取代的氨基四唑衍生物的直接途径，并且可以在克规模上实现。因此，容易合成N- (杂芳基)-和N-（芳基）氨基四唑为研究这些化合物作为功能材料或候选药物的应用前景提供了新的机会。

  DOI：

  10.1016/j.tet.2021.132563
• 作为产物：
  描述：

  3-氯-2,4-戊二酮 、 3-氯苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 生成 N-(3-chlorophenyl)-2-oxo-propanehydrazonoyl chloride
  参考文献：
  名称：

  新型NO供体吡唑并[3,4- d ]哒嗪5,6-二氧化物的设计与合成

  摘要：

  一种简单有效的合成2 H-吡唑并[3,4- d ]哒嗪5,6-二氧化物的方法包括将可及的3,4-二乙酰基-5-甲基-1 H-吡唑转化为相应的1， 4-二恶英，随后是它们的N 2 O 4介导的氧化环化作用。所有转化都在温和条件下以高产到高产进行。根据Griess分析，合成的2 H-吡唑并[3,4- d ]哒嗪5,6-二氧化物显示出有希望的NO供体谱，可在宽范围的浓度下产生NO。

  DOI：

  10.1016/j.mencom.2021.01.012

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。
• Heterocyclisation of 2,5-diacetyl-3,4-disubstituted-thieno[2,3-b]Thiophene Bis-Thiosemicarbazones Leading to Bis-Thiazoles and Bis-1,3,4-thiadiazoles as Anti-breast Cancer Agents
  作者：Sobhi M. Gomha、Mohamed G. Badrey、Mastoura M. Edrees

  DOI：10.3184/174751916x14537182696214

  日期：2016.2

  In this paper, the synthesis of bis-thiazoles and bis-1,3,4-thiadiazoles linked to a thienothiophene nucleus is described. The synthesis was achieved through interaction between 2,5-diacetylthieno[2,3-b]thiophene bis-thiosemicarbazones with a variety of hydrazonyl halides in a basic medium. All the synthesised compounds were characterised by IR, ¹H NMR, ¹³C NMR and mass spectroscopic analyses. The newly synthesised compounds represent a variety of novel polyheteroatomic moieties containing nitrogen and sulfur. Most of the synthesised compounds were evaluated for their antitumour activity against the breast cancer MCF-7 cell line. The results revealed that four compounds are equipotent to tamoxifen (IC₅₀ = 8.04 μg mL⁻¹) with IC₅₀ = 8.23, 8.26, 8.68 and 9.12 μg mL⁻¹ respectively.

  本文介绍了与噻吩核相连的双噻唑和双-1,3,4-噻二唑的合成。合成是通过 2,5-二乙酰基噻吩并[2,3-b]噻吩双硫代氨基甲酸酯与多种肼基卤化物在碱性介质中的相互作用实现的。所有合成化合物都通过红外光谱、1H NMR、13C NMR 和质谱分析进行了表征。新合成的化合物代表了多种新型含氮和硫的多原子分子。对大部分合成化合物进行了抗乳腺癌 MCF-7 细胞系的抗肿瘤活性评估。结果表明，四种化合物与他莫昔芬具有等效性（IC50 = 8.04 μg mL-1），IC50 分别为 8.23、8.26、8.68 和 9.12 μg mL-1。
• Synthesis and SAR Study of the Novel Thiadiazole–Imidazole Derivatives as a New Anticancer Agents
  作者：Sobhi Mohamed Gomha、Hassan Mohamed Abdel-aziz、Khaled Dessouky Khalil

  DOI：10.1248/cpb.c16-00344

  日期：——

  In the present study, a novel series of 2-(2-(3-aryl-5-substituted-1,3,4-thiadiazol-2(3H)-ylidene)hydrazinyl)-4,4-diphenyl-1H-imidazol-5(4H)-one derivatives were designed and prepared via the reaction of the most versatile, hitherto unreported 2-(5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-N-phenylhydrazinecarbothioamide with the appropriate hydrazonoyl halides. In addition, some thiazole derivatives were prepared. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses. Some of the newly synthesized compounds have been evaluated for their anticancer activity against a liver carcinoma cell line HEPG2-1. Moreover, their structure–activity relationship (SAR) was explored for further development in this area. The results indicated that many of the tested compounds showed moderate to high anticancer activity with respective to doxorubicin as a reference drug. Consequently, the new synthesized series of thiadiazole–imidazole derivatives are considered as powerful anticancer agents.

  本研究中，设计并合成了一系列新型2-(2-(3-芳基-5-取代-1,3,4-噻二唑-2(3H)-亚基)酰肼基)-4,4-二苯基-1H-咪唑-5(4H)-酮衍生物，其合成方法是通过将迄今未报道的最通用的2-(5-氧-4,4-二苯基-4,5-二氢-1H-咪唑-2-基)-N-苯基酰肼硫脲与适当的酰肼基卤化物反应。此外，还合成了一些噻唑衍生物。新合成化合物的结构基于光谱证据及其替代合成方法进行确定。其中一些新合成化合物已针对肝癌HEPG2-1细胞系评估了其抗癌活性。此外，探讨了它们的构效关系(SAR)，为进一步开发该领域提供依据。结果表明，许多测试化合物显示出中等到高水平的抗癌活性，相对于参考药物阿霉素。因此，新合成的一系列噻二唑-咪唑衍生物被认为是强效的抗癌剂。
• 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。
• Microwave-Assisted Synthesis of Antimicrobial Agents Containing Carbazole and Thiazole Moieties
  作者：Rabab S. Jasass、Fatimah Alshehrei、Thoraya A. Farghaly

  DOI：10.1002/jhet.3253

  日期：2018.9

  An efficient synthesis of new derivatives of carbazole incorporated with thiazole moiety via the reaction of carbazole thiosemicarbazone with hydrazonoyl chloride under microwave irradiation. The spectral results and the electronic absorption data proved the postulated structures of the resulting compounds. The starting thiosemicarbazone and all the new derivatives were evaluated against two fungi

  通过咔唑硫代半咔唑与carb酰氯在微波辐射下的反应，可有效合成带有噻唑部分的咔唑新衍生物。光谱结果和电子吸收数据证明了所得化合物的假定结构。起始缩氨基硫脲和所有的新衍生物对两种真菌，四个G进行了评价+菌和G -细菌。与使用的标准杀菌剂和杀真菌剂相比，所获得的结果探索了某些测试化合物的高效力。