1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide | 39643-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide
• 英文别名: 1-[(5-bromo-2-hydroxyphenyl)methylideneamino]-3-phenylthiourea
• CAS: 39643-68-0
• 化学式: C₁₄H₁₂BrN₃OS
• 分子量: 350.239
• InChiKey: VIJHSSPHLZACQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide 、 二丁基二氯化锡 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.25h， 以62%的产率得到
  参考文献：
  名称：

  Diorganotin Complexes with N(4)-Phenylthiosemicarbazones: Synthesis, Spectroscopic Characterization, and Antibacterial Activity

  摘要：

  The organotin(IV) complexes, SnPh2La (1), SnMe2La (2), SnBu2La (3), SnPh2Lb (4), SnMe2Lb (5), SnPh2Lc (6), SnMe2Lc (7), and SnBu2Lc (8) were obtained by reaction of SnR2Cl2 (R = Ph, Me, and Bu) with 1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide (H2La), 1-((2-hydroxynaphthalen-1-yl)methylene)-4-phenylthiosemicarbazide (H2Lb), and 1-(2-hydroxy-3-methoxybenzylidene)-4-phenylthiosemicarbazide (H2Lc). The synthesized complexes have been investigated by elemental analysis, IR, H-1 NMR, and Sn-119 NMR spectroscopy. The data show that the thiosemicarbazone acts as a tridentate dianionic ligand and coordinates via the thiol group, imine nitrogen, and phenolic oxygen. The coordination number of tin is 5. The in vitro antibacterial activities of the ligands and their complexes have been evaluated against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria and compared with the standard antibacterial drugs. [Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the following free supplemental files: Additional figures and tables]

  DOI：

  10.1080/10426507.2013.777727
• 作为产物：
  描述：

  4-苯基-3-硫代氨基脲 、 5-溴水杨醛 以 乙醇 为溶剂， 以70%的产率得到1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide
  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

• Heteroleptic complexes of Zn(II) based on 1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide: Synthesis, structural characterization, theoretical studies and antibacterial activity
  作者：Mohammad Azarkish、Alireza Akbari、Tahereh Sedaghat、Jim Simpson

  DOI：10.1016/j.molstruc.2016.12.080

  日期：2017.4

  Abstract Four new ternary complexes, [ZnL (2,2′-bipy)] ( 1 ), Zn 2 L 2 (4,4′-bipy)] ( 2 ), [ZnL(Imd)]·H 2 O ( 3 ) and [ZnL 3 (MeImd)] ( 4 ), have been synthesized from the reaction of Zn(II) acetate with 1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide (H 2 L) in the presence of a heterocyclic base, 2,2′-bipyridine, 4,4′-bipyridine, imidazole or 2-methylimidazole, as an auxiliary ligand. The complexes

  摘要 四种新的三元配合物，[ZnL (2,2'-bipy)] ( 1 ), Zn 2 L 2 (4,4'-bipy)] ( 2 ), [ZnL(Imd)]·H 2 O ( 3 ) ) 和 [ZnL 3 (MeImd)] ( 4 )，是由醋酸锌与 1-(5-bromo-2-hydroxybenzylidene)-4-phenylthiosemicarbazide (H 2 L) 反应合成的杂环碱、2,2'-联吡啶、4,4'-联吡啶、咪唑或2-甲基咪唑作为辅助配体。已通过元素分析和 FT-IR、UV-Vis 和 1 HNMR 光谱研究了配合物。这些数据表明缩氨基硫脲作为三齿双阴离子配体并通过硫醇基团、亚胺氮和酚氧进行配位。配位球由二级配体的氮原子完成。1 的结构也被 X 射线晶体学证实，并显示为一个五坐标复合物，在方锥体和三角双锥体之间具有配位几何。密度泛函理论 (DFT) 计算包括几何优化、振动频率和电子吸收，已使用
• Thiol-Reactive Arylsulfonate Masks for Phenolate Donors in Antiproliferative Iron Prochelators
  作者：Wangbin Wu、Yu-Shien Sung、Elisa Tomat

  DOI：10.1021/acs.inorgchem.2c03250

  日期：2022.12.12

  chelators. The new prochelators liberate a tridentate thiosemicarbazone intracellularly upon reaction with abundant nucleophile glutathione (GSH). A 5-bromo-substituted salicylaldehyde thiosemicarbazone (STC4) was selected for the chelator unit because of its antiproliferative activity at low micromolar levels in a panel of six cancer cell lines. The arylsulfonate prochelators were assessed in vitro

  三齿缩氨基硫脲是几个铁螯合剂家族中的一种，在抗癌药物的发现中显示出了有希望的结果，因为它们针对的是恶性细胞对铁的需求增加。前螯合策略（其中螯合剂在特定条件下释放）有可能避免脱靶金属结合（例如，在血液中）并最大限度地减少不需要的副作用。我们报告了一种预螯合方法，该方法采用芳基磺酸酯来掩蔽水杨醛基螯合剂的酚盐供体。新的前螯合剂与丰富的亲核体谷胱甘肽（GSH）反应后在细胞内释放三齿缩氨基硫脲。选择 5-溴取代的水杨醛缩氨基硫脲 (STC4) 作为螯合剂单元，因为它在六种癌细胞系中以低微摩尔水平具有抗增殖活性。在体外评估芳基磺酸盐预螯合剂的稳定性、消除金属结合的能力以及在 GSH 存在下的反应性。基于细胞的测定表明，24 小时后，芳基磺酸盐掩蔽的预螯合剂相对于母体化合物表现出更高的抗增殖活性。通过胞质铁结合和铁补充效应以及细胞周期分析的测定证实了细胞内螯合剂的激活和释放。本研究引入了 1,3,4-
• Ligand control on the synthesis and redox potency of mononuclear manganese-(III) and -(IV) complexes with tridentate ONS co-ordination
  作者：Rina Mukhopadhyay、Samiran Bhattacharjee、Ramgopal Bhattacharyya

  DOI：10.1039/dt9940002799

  日期：——

  Trifunctional (ONS) Schiff bases H2L1 and H2L2 (H2L1 = 5-R-salicylaldehyde thiosemicarbazone; H2L2 = 5-R-salicylaldehyde 4-phenylthiosemicarbazone; R = H, Me or Br) furnished manganese(IV) complexes of the type [MnL2] (L = L1 or L2), whereas H2L3 and H2L4H2L3 = S-methyl 3-[(5-R-2-hydroxyphenyl)-methylene]dithiocarbazate; H2L4 = S-benzyl 3-[(5-R-2-hydroxyphenyl)methylene]dithiocarbazate; R = H, Me or Br} afforded manganese(III) complexes of the type [MnL(O2CMe)] or [MnL(acac)] (acac = acetylacetonate, L = L3 or L4), when treated with Mn(II)(O2CMe)2.4H2O or [Mn(III)(acac)3] in alcoholic media in the air. The room-temperature magnetic moments confirm the corresponding oxidation states in the complexes. The EPR spectra of the manganese(IV) complexes in frozen dimethylformamide (dmf)-methanol solution show weak and strong signals at [g] almost-equal-to 4.0 and almost-equal-to 2.0, respectively, implying a small zero-field splitting. The [g] almost-equal-to 2.0 signal shows hyperfine (due to Mn-55) as well as forbidden lines. Cyclic voltammograms of all the complexes scanned in dmf showed reversible to quasi-reversible Mn(IV)-Mn(III) couples the E298-degrees values of which are significantly affected by the electronic effects of the R substituents in the salicyl phenyl ring and the R' substituents attached to the carbon atom bound to the thiolate functionality of the ligands. The Hammett sigma(p) values of the R substituents are linearly correlated with the E298-degrees values.
• Artizzu; Bonsignore; Loy, Il Farmaco, 1995, vol. 50, # 12, p. 853 - 856
  作者：Artizzu、Bonsignore、Loy、Calignano

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ni: MVol.C2, 7.5.2, page 686 - 689
  作者：

  DOI：——

  日期：——