1-(2-hydroxyphenyl)ethanone (E)-thiosemicarbazone | 7441-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2-hydroxyphenyl)ethanone (E)-thiosemicarbazone
• 英文别名: 2-hydroxyacetophenone thiosemicarbazone；o-hydroxyacetophenone thiosemicarbazone；1-(2-hydroxyphenyl)ethan-1-one thiosemicarbazone；1-(2-hydroxy-phenyl)-ethanone thiosemicarbazone；(2E)-2-[1-(2-hydroxyphenyl)ethylidene]hydrazinecarbothioamide；[(E)-1-(2-hydroxyphenyl)ethylideneamino]thiourea
• CAS: 7441-53-4
• 化学式: C₉H₁₁N₃OS
• 分子量: 209.272
• InChiKey: LXYOGTSBYWAKMS-IZZDOVSWSA-N

物化性质

• 熔点：
  167 °C(Solv: methanol (67-56-1))
• 沸点：
  367.8±44.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 、 氨基硫脲 以 乙醇 为溶剂， 生成 1-(2-hydroxyphenyl)ethanone (E)-thiosemicarbazone
  参考文献：
  名称：

  Synthesis, structure, spectroscopic properties and cytotoxic effect of some thiosemicarbazone complexes of palladium

  摘要：

  水杨醛缩氨基硫脲(H2L1)、2-羟基苯乙酮缩氨基硫脲(H2L2)和2-羟基萘醛缩氨基硫脲(H2L3)(通用缩写为H2L,其中H2代表两个可解离的质子,分别为酚羟基和肼基的质子)与Na2[PdCl4]反应生成了一类聚合物配合物[{Pd(L)}n]。这类聚合物与两个单齿配体,例如三苯基膦(PPh3)和4-甲基吡啶(pic),反应生成了配合物[Pd(L)(D)]。从硫卡巴脒与[Pd(PPh3)2Cl2]和[Pd(pic)2Cl2]的反应中也可以得到这类混合配体配合物。已测定了配合物[Pd(L1)(PPh3)]和[Pd(L2)(pic)]的晶体结构。[Pd(L)(D)]配合物具有特征的1H NMR图谱与明显的可见光区和紫外区吸收。它们在环境温度下可见光区也具有强荧光。这类配合物与四个临床药物即顺铂、BCNU、5-氟尿嘧啶(5-FU)和羟基脲共同进行了体外细胞毒性屏幕测试,测试对象为两个人类癌细胞系,即早幼粒细胞白血病HL-60和组织细胞淋巴瘤U-937。与上述两种细胞系中作为参比试剂的抗癌药物相比,[Pd(L2)(PPh3)]显示了最低的IC50值,其细胞毒性更为明显。用[Pd(L2)(PPh3)]在HL-60细胞上进行的凋亡研究证实,10μM浓度下的该配合物诱导细胞凋亡的程度要大于顺铂和喜树碱。

  DOI：

  10.1039/b707448d

文献信息

• The conformational analysis of 2-hydroxyaryl Schiff thiosemicarbazones
  作者：M. Krasowska、A. Kochel、A. Filarowski

  DOI：10.1039/b921402j

  日期：——

  X-Ray measurements and quantum-mechanical (B3LYP and MP2) calculations of 2-hydroxyaryl Schiff thiosemicarbazones were performed to describe the tautomeric and conformational equilibrium. The structures of five N-alkyl- and N-aryl-thiosemicarbazone derivatives were determined by single-crystal X-ray diffraction at 100 K. The conformational schemes for determining the various states of the compounds were calculated by the DFT (B3LYP/6-31+G(d,p)) method. The difference between the phenolic and heterocyclic derivatives with respect to the OH ⇆ HN tautomeric equilibrium is shown. The influence of the environment's polarity on CS ⇆ SC conformational equilibrium was determined by DFT calculations. The potential energy curves for rotating particular fragments of the thiosemicarbazone moiety were calculated to estimate the rotational energetic barriers.

  进行了2-羟基芳基席夫碱硫半缩氨基脲的X射线测量和量子力学（B3LYP和MP2）计算，以描述互变异构和构象平衡。通过在100 K下进行的单晶X射线衍射，确定了五种N-烷基和N-芳基硫半缩氨基脲衍生物的结构。通过DFT（B3LYP/6-31+G(d,p)）方法计算了确定化合物各种状态的构象方案。展示了酚类和杂环衍生物在OH ⇆ HN互变异构平衡方面的差异。通过DFT计算确定了环境极性对CS ⇆ SC构象平衡的影响。计算了旋转硫半缩氨基脲部分特定片段的势能曲线，以估计旋转能垒。
• [EN] ANTI-PARASITIC COMPOUNDS AND METHODS OF THEIR USE<br/>[FR] COMPOSES ANTIPARASITAIRES ET LEURS PROCEDES D'UTILISATION
  申请人：UNIV CALIFORNIA

  公开号：WO2005087211A1

  公开（公告）日：2005-09-22

  The present invention provides a novel class of compounds that disrupt the parasitic infectious life cycle and serve as promising agents for anti-parasitic therapy.

  本发明提供了一类新型化合物，可以破坏寄生虫的传染生命周期，并作为抗寄生虫疗法的有希望的药物。
• Anti-infective compounds
  申请人：Brodin Priscille

  公开号：US20110178077A1

  公开（公告）日：2011-07-21

  The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及小分子化合物及其在治疗细菌感染，特别是结核病方面的用途。
• Thiadiazoline derivative
  申请人：Murakata Chikara

  公开号：US20060074113A1

  公开（公告）日：2006-04-06

  (wherein R 1 and R 4 are the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkynyl, substituted or unsubstituted lower alkenyl, or the like; R 5 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like; R 2 represents —C(═W)R 6 or the like; R 3 represents a hydrogen atom, —C(═W A )R 6A , or the like) Antitumor agents which comprises a thiadiazoline derivative represented by the aforementioned general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient are provided.

  提供了一种抗肿瘤剂，其中R1和R4相同或不同，每个代表氢原子，取代或未取代的低级烷基，取代或未取代的低级炔基，取代或未取代的低级烯基或类似物；R5代表取代或未取代的杂环基，取代或未取代的芳基或类似物；R2代表-C（═W）R6或类似物；R3代表氢原子，-C（═WA）R6A或类似物。该抗肿瘤剂包含由上述通式（I）表示的噻二唑啉衍生物或其药理学上可接受的盐作为活性成分。
• THIADIAZOLINE DERIVATIVE
  申请人：MURAKATA Chikara

  公开号：US20080207706A1

  公开（公告）日：2008-08-28

  (wherein R 1 and R 4 are the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkynyl, substituted or unsubstituted lower alkenyl, or the like; R 5 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like; R 2 represents —C(═W)R 6 or the like; R 3 represents a hydrogen atom, —C(═W A )R 6A , or the like) Antitumor agents which comprises a thiadiazoline derivative represented by the aforementioned general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient are provided.

  提供了一种抗肿瘤剂，其包括由上述一般式（I）表示的噻二唑啉衍生物或其药学上可接受的盐作为活性成分，其中R1和R4相同或不同，每个代表氢原子，取代或未取代的低碳基，取代或未取代的低炔基，取代或未取代的低烯基或类似物; R5代表取代或未取代的杂环基，取代或未取代的芳基或类似物; R2代表-C（═W）R6或类似物; R3代表氢原子，-C（═WA）R6A或类似物。