Pyruvoylchlorid-1-<(2,4-dichlorphenyl)-hydrazon> | 37104-26-0

• 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: Pyruvoylchlorid-1-<(2,4-dichlorphenyl)-hydrazon>
• 英文别名: N'-(2,4-dichloro-phenyl)-pyruvohydrazonoyl chloride；N'-(2,4-Dichlor-phenyl)-pyruvohydrazonoylchlorid；α-Chlor-α-(2.4-dichlor-phenylhydrazono)-aceton；N-(2,4-dichlorophenyl)-2-oxo-propanehydrazonoyl chloride；pyruvoyl chloride 1-[(2,4-dichlorophenyl)hydrazone]；N-(2,4-dichlorophenyl)-2-oxopropanehydrazonoyl chloride
• CAS: 37104-26-0
• 化学式: C₉H₇Cl₃N₂O
• 分子量: 265.526
• InChiKey: SOTSGIPEYHCULQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 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：

  Pyruvoylchlorid-1-<(2,4-dichlorphenyl)-hydrazon> 在 ammonium sulfide 、 丙酮 作用下， 生成 N'-(2,4-dichloro-phenyl)-pyruvohydrazonic acid-thioanhydride
  参考文献：
  名称：

  Buelow; Seidel, Chemische Berichte, 1924, vol. 57, p. 362

  摘要：

  DOI：
• 作为产物：
  描述：

  3-oxo-2-(2-phenylhydrazono)butanoic acid 在 磺酰氯 、 溶剂黄146 作用下， 生成 Pyruvoylchlorid-1-<(2,4-dichlorphenyl)-hydrazon>
  参考文献：
  名称：

  Neber; Woerner, Justus Liebigs Annalen der Chemie, 1936, vol. 526, p. 175

  摘要：

  DOI：

文献信息

• 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 of New 2-Naphthyl Ethers and Their Protective Activities against DNA Damage Induced by Bleomycin-Iron
  作者：Bakr F. Abdel-Wahab、Abdel-Aziz S. El-Ahl、Farid A. Badria

  DOI：10.1248/cpb.57.1348

  日期：——

  2:4,5-dianhydride produced bis-diazo compounds 10a-c and dimide 11 respectively. All new compounds were tested for their protective activity against DNA damage induced by bleomycin-iron complex. Compound 2 showed the greatest protection against DNA damage, thus diminishing chromogen formation between the damaged DNA and thiobarbituric acid.

  2-萘氧基乙酸与硫代氨基脲在磷酰氯存在下反应，然后用苯乙酰胺处理，导致形成咪唑并[2,1-b] [1,3,4]噻二唑3a-c。2-（萘-3-基氧基）乙酰肼4用2-（2-芳基肼基）-3-氧代丁酸乙酯（5a-c），2-甲氧基亚甲基）丙二腈或乙基2-氰基-3,3-双（甲硫基丙烯酸甲酯导致形成取代的吡唑6-8。酰肼4与酰肼基氯9a-c和1,2,4,5-苯四羧酸-1,2：4,5-二酐的反应分别产生了双重氮化合物10a-c和二酰亚胺11。测试了所有新化合物对博来霉素-铁配合物诱导的DNA损伤的保护活性。化合物2对DNA损伤显示出最大的保护作用，
• Synthesis and Characterization of Some New Heterocycles Incorporating the 1-Phenyl-5-(2-thienyl)pyrazole Moiety
  作者：Bakr F. Abdel-Wahab、Abdel-Aziz Sayed El-Ahl

  DOI：10.1080/10426500902758956

  日期：2010.1.29

  4 was prepared from 2-acetylthio- phene by reaction with diethyl oxalate and phenylhydrazine followed by hydrazine hydrate. The reaction of the hydrazide 4 with phthalic anhydride, aromatic aldehydes, and alkene derivatives gave imide 5, hydrazones 6a–d, and bis-pyrazoles 7 and 8, respectively, while its reaction with phenyl isothiocyanate led to thiosemicarbazide 9. The reaction of the latter with

  1-苯基-3-(2-噻吩基)-1H-吡唑-5-碳酰肼 4 由 2-乙酰噻吩通过与草酸二乙酯和苯肼反应，然后与水合肼反应制备。酰肼 4 与邻苯二甲酸酐、芳香醛和烯烃衍生物的反应分别产生了酰亚胺 5、腙 6a-d 和双吡唑 7 和 8，而它与异硫氰酸苯酯的反应产生了氨基硫脲 9。后者与溴乙酸乙酯和苯甲酰溴分别得到 4-噻唑烷酮 10 和 1,3-噻唑 11 衍生物。4 在氢氧化钾存在下与二硫化碳反应得到肼碳二硫代酸钾衍生物 12，其用作制备 2-硫代噻唑-3(2H)-基)-5-(2-噻吩基)-1H 的原料-吡唑-3-甲酰胺14；1,3, 4-噻二唑-2(3H)-亚基)-1-苯基-5-(2-噻吩基)-1H-吡唑-3-碳酰肼16a-c；4-氨基-5-硫代-4,5-二氢-1H-1,2,4-三唑-3-基)吡唑衍生物13；席夫碱 17a,b; 和 1,2,4-三唑并[3,4-b][1,3,4]噻二嗪衍生物
• Synthesis and antimicrobial evaluation of some 1,3-thiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazine derivatives including a 5-(benzofuran-2-yl)-1-phenylpyrazole moiety
  作者：Bakr F. Abdel-Wahab、Hatem A. Abdel-Aziz、Essam M. Ahmed

  DOI：10.1007/s00706-008-0099-x

  日期：2009.6

  hydrate, phenacyl bromide, or hydrazonoyl chlorides afforded 1,2,4-triazole, 1,3-thiazole, and 1,3,4-thiadiazoles. Reaction of 1,2,4-triazole with phenacyl bromide or hydrazonoyl chlorides afforded the corresponding 1,2,4-triazolo[3,4-b][1, 3, 4]-thiadiazines. All these new compounds were screened for antibacterial and antifungal activity. Some had promising activity. Graphical abstract

  摘要通过在氢氧化钾存在下用二硫化碳处理酰肼来制备肼基二硫代硫酸钾。该钾盐与水合肼，苯甲酰溴或酰肼基氯反应，得到1,2,4-三唑，1,3-噻唑和1,3,4-噻二唑。1,2,4-三唑与苯甲酰溴或酰肼基氯反应，得到相应的1,2,4-三唑并[3,4- b ] [1、3、4]-噻二嗪。筛选所有这些新化合物的抗菌和抗真菌活性。有些活动前景良好。 图形概要