3,5-dibromosalicylidene thiosemicarbazone | 6292-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-dibromosalicylidene thiosemicarbazone
• 英文别名: 2-hydroxy-3,5-dibromobenzylidenehydrazino thiocarboamide；[(3,5-dibromo-2-hydroxyphenyl)methylideneamino]thiourea
• CAS: 6292-75-7
• 化学式: C₈H₇Br₂N₃OS
• 分子量: 353.037
• InChiKey: KOUSSFCOFUJIJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dibromosalicylidene thiosemicarbazone 、 1-methyl-1-mesityl-3-(2-chloro-1-oxoethyl)cyclobutane 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 2-hydroxy-3,5-dibromobenzaldehyde [4-(3-mesityl-3-methylcyclobutyl)-1,3-thiazol-2-yl]hydrazone
  参考文献：
  名称：

  一些含有3-取代的环丁烷环的新的噻唑基hydr衍生物的合成，抗菌和抗真菌活性。

  摘要：

  合成，组合并表征了一系列席夫碱，这些席夫碱将2,4-二取代的噻唑和环丁烷环以及rings部分结合在同一分子中，并分别针对四种细菌和热带念珠菌进行了筛选，以筛选其对微生物的抗菌和抗真菌活性。原始化合物的结构通过分析和光谱法（FT-IR，（1）H NMR和（13）C NMR）方法以及元素分析得到确认。化合物的抗菌和抗真菌活性以及MIC值都有报道。在测试的化合物中，提供MIC值为16微克ml（-1）的最有效化合物是仅对付热带假丝酵母和枯草芽孢杆菌2个，对付枯草芽孢杆菌3个。

  DOI：

  10.1016/j.ejmech.2005.01.013
• 作为产物：
  描述：

  3,5-二溴水杨醛 、 氨基硫脲 以 乙醇 为溶剂， 以72%的产率得到3,5-dibromosalicylidene thiosemicarbazone
  参考文献：
  名称：

  Synthesis and Characterization of Some New Cu(II), Ni(II) and Zn(II) Complexes with Salicylidene Thiosemicarbazones: Antibacterial, Antifungal and in Vitro Antileukemia Activity

  摘要：

  合成了32个新的Cu(II)、Ni(II)和Zn(II)配合物(1-32)与水杨醛缩硫代氨基脲(H2L1-H2L10)。水杨醛缩硫代氨基脲，通式为(X)N-NH-C(S)-NH(Y)，通过2-羟基苯甲醛及其衍生物(X)与硫代氨基脲或4-苯基硫代氨基脲(Y=H, C6H5)的缩合反应制备。新形成的化合物的表征通过1H-NMR、13C-NMR、IR光谱、元素分析、磁化学、热分析和摩尔电导测量进行。此外，配合物5的结构通过X射线衍射方法确定。所有配体和金属配合物都作为抑制人白血病(HL-60)细胞生长以及抗菌和抗真菌活性的抑制剂进行了测试。

  DOI：

  10.3390/molecules18088812

文献信息

• 2-（2-苄亚肼基）-5-（1，2，4-三唑-1-基）噻唑 及其制备与应用
  申请人：湖南大学

  公开号：CN104774199B

  公开（公告）日：2017-03-08

  本发明涉及化学结构式I所示的2‑（2‑苄亚肼基）‑5‑（1，2，4‑三唑‑1‑基）噻唑或其盐：其中，R选自：氢、氘、C1～C2烷基、C3～C4直链或支链烷基；X1～X5选自：氢、氘、C1～C2烷基、羟基、甲氧基、乙氧基、氟、氯、溴、硝基；2‑（2‑苄亚肼基）‑5‑（1，2，4‑三唑‑1‑基）噻唑在制备流感病毒神经氨酸酶抑制剂中的应用。
• DNA binding and photocleavage properties of two mixed-ligand oxovanadium complexes
  作者：Yi-fan Du、Jia-Zheng Lu、Hai-wei Guo、Jing Jiang、Ping Chao、Fei Chen、Jie-Ming Pan

  DOI：10.1007/s11243-010-9404-8

  日期：2010.10

  An oxovanadium complex [VO(satsc)(bipy)] (1) (satsc = salicylaldehyde thiosemicarbazone, bipy = 2,2′-bipyridine) and its dibromo derivative [VO(3,5-dibrsatsc)(bipy)] (2) (3,5-dibrsatsc = 3,5-dibromosalicylaldehyde thiosemicarbazone) have been synthesized and characterized by elemental analysis, IR, ES-MS and 1H NMR. The interaction of these two complexes with calf-thymus DNA (CT-DNA) was studied using UV/Vis, fluorescence spectroscopic titration, viscosity measurements and thermal denaturation. The results suggest that complexes 1 and 2 interact with CT-DNA by intercalative modes. The DNA-binding affinity of complex 1 is larger than that of complex 2. In addition, their photocleavage reactions with pBR322 supercoiled plasmid DNA were investigated by gel electrophoresis experiments. Both complexes exhibit significant DNA cleavage activity, and complex 1 showed greater cleaving efficiency than complex 2.

  牛钒配合物[VO(satsc)(bipy)](1)（satsc = 水杨醛缩氨基硫脲，bipy = 2,2′-联吡啶）及其二溴衍生物[VO(3,5-dibrsatsc)(bipy)](2)（3,5-dibrsatsc = 3,5-二溴水杨醛缩氨基硫脲）已经合成，并通过元素分析、红外光谱、电子轰击质谱和1H核磁共振进行了表征。利用紫外/可见光、荧光光谱滴定、粘度测量和热变性研究了这两种配合物与小牛胸腺DNA（CT-DNA）的相互作用。结果表明，配合物1和2以插入模式与CT-DNA相互作用。配合物1与DNA的结合亲和力大于配合物2。此外，通过凝胶电泳实验研究了它们与pBR322超螺旋质粒DNA的光裂解反应。两种配合物均表现出显著的DNA裂解活性，且配合物1的裂解效率高于配合物2。
• Design, synthesis and biological evaluation of novel thiazole derivatives as potent FabH inhibitors
  作者：Peng-Cheng Lv、Kai-Rui Wang、Ying Yang、Wen-Jun Mao、Jin Chen、Jing Xiong、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2009.09.111

  日期：2009.12

  Fatty acid biosynthesis is essential for bacterial survival. Components of this biosynthetic pathway have been identified as attractive targets for the development of new antibacterial agents. FabH, beta-ketoacylacyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram positive and negative bacteria. Three series of Schiff bases containing thiazole template were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 11 and 18 were potent inhibitors of E. coli FabH. (C) 2009 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors
  作者：Peng-Cheng Lv、Chang-Fang Zhou、Jin Chen、Peng-Gang Liu、Kai-Rui Wang、Wen-Jun Mao、Huan-Qiu Li、Ying Yang、Jing Xiong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.10.051

  日期：2010.1

  Two series of thiazolidinone derivatives designing for potential EGFR and HER-2 kinase inhibitors have been discovered. Some of them exhibited significant EGFR and HER-2 inhibitory activity. Compound 2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one (12) displayed the most potent inhibitory activity (IC50 = 0.09 mu M for EGFR and IC50 = 0.42 mu M for HER-2), comparable to the positive control erlotinib. Docking simulation was performed to position compound 12 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the thiazolidinone derivatives own high antiproliferative activity against MCF-7. Compound 12 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. (C) 2009 Elsevier Ltd. All rights reserved.
• Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations
  作者：Nabil S. Youssef、Ahmed M.A. El-Seidy、Marco Schiavoni、Brunilde Castano、Fabio Ragaini、Emma Gallo、Alessandro Caselli

  DOI：10.1016/j.jorganchem.2012.03.018

  日期：2012.9

  New copper complexes of several thiosemicarbazones have been prepared and characterized. All complexes have been prepared by employing Cu (II) acetate hydrate, but analytical and spectroscopical data for the isolated complexes revealed that in most cases a reduction to copper (I) occurred. Cyclopropanation reactions of several olefins by ethyldiazoacetate (EDA) in the presence of catalytic amounts of the complexes were examined. The reported results showed that all complexes are competent catalysts for the cyclopropanation reaction of unactivated olefins. Cyclopropanes were obtained in high yields (up to 97%, TON up to 18,400) with moderate to excellent diastereoselectivities (up to >99%). (C) 2012 Elsevier B. V. All rights reserved.