picolinaldehyde-S-benzyldithiocarbazate | 66415-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: picolinaldehyde-S-benzyldithiocarbazate
• 英文别名: S-benzyl-β-N-((2-pyridyl)-methylene)-dithiocarbazate；pyridine-2-carboxaldehyde S-benzyldithiocarbazate；2-pyridinecarbaldehyde S-benzyl dithiocarbazate；HPCSBC；benzyl N-(pyridin-2-ylmethylideneamino)carbamodithioate
• CAS: 66415-74-5
• 化学式: C₁₄H₁₃N₃S₂
• 分子量: 287.409
• InChiKey: VLFMYRBJDHAVEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  RuH₂(CO)(PPh₃)₃ 、 picolinaldehyde-S-benzyldithiocarbazate 以 乙醇 、 苯 为溶剂， 以71%的产率得到{hydrido-trans-(triphenylphosphine)2(carbonyl)(PCD)ruthenium(II)}
  参考文献：
  名称：

  Gopinathan, Sarada; Deshpande, S. S.; Gopinathan, C., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1989, vol. 19, p. 321 - 338

  摘要：

  DOI：
• 作为产物：
  描述：

  吡啶-2-甲醛 、 S-benzyldithiocarbazate 以 乙醇 为溶剂， 反应 0.25h， 以79.9%的产率得到picolinaldehyde-S-benzyldithiocarbazate
  参考文献：
  名称：

  杂环二硫代氨基甲酸铁螯合剂：铁配位化学和生物活性†

  摘要：

  据报道，一系列杂环二硫代氨基甲酸酯席夫碱配体的铁配位和生物化学具有作为铁螯合剂的活性，可用于治疗铁超载以及癌症。配体类似于我们之前研究的带有NNO和NNS供体的三齿hetero和硫代半碳氮螯合剂。这项工作中的二硫代氨基甲酸酯席夫碱配体也是NNS螯合剂，形成稳定的低自旋三价铁和亚铁配合物，并且都已被分离。另外一个不寻常的羟基化的配位体衍生物已被确定经由铁诱导的氧化反应。这些配合物的X射线晶体学和光谱表征已经进行，并且还研究了电化学性质。所有的Fe络合物均表现出完全可逆的Fe III / II在混合水性溶剂中的偶合电位比在类似的硫代半碳酰胺Fe络合物中发现的电位高。检查了二硫代氨基甲酸酯基希夫碱配体从细胞中动员铁以及防止铁从转铁蛋白摄取的能力，并且相对于已知的对照例如临床上重要的铁螯合剂去铁胺，所有配体都有效地螯合了细胞内铁。衍生自2-吡啶甲醛的席夫碱配体对SK-N-MC神经上皮瘤（癌细胞）细

  DOI：

  10.1039/c2dt12387h

文献信息

• 1,3,4-Thia- and -selenadiazole and 1,2,4-triazolo[4,3-a]pyrimidine derivatives from hydrazonoyl halides
  作者：Nadia A. Abdel-Riheem、Nora M. Rateb、Ali A. Al-Atoom、Abdou O. Abdelhamid

  DOI：10.1002/hc.10156

  日期：——

  1,2,4-Triazolo[4,3-a]pyrimidines, thiadiazolines, selenadiazolines, and unsymmetrical azines were synthesized via reactions of a 4-isopropylbenzoyl bromide 4-nitrophenylhydrazone with each of potassium thiocyanate, potassium selenocyanate, ethyl 6-methyl-4-[4-(methylethyl)phenyl]-2-methylthio-3,4-dihydropyrimidine-5-carboxylate, and alkyl carbodithioate. © 2003 Wiley Periodicals, Inc. Heteroatom Chem

  1,2,4-三唑并[4,3-a]嘧啶、噻二唑啉、硒二唑啉和不对称吖嗪通过 4-异丙基苯甲酰溴 4-硝基苯腙与硫氰酸钾、硒氰酸钾、6-甲基乙基4-[4-(甲基乙基)苯基]-2-甲硫基-3,4-二氢嘧啶-5-羧酸酯和碳二硫代烷基酯。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:421–426, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10156
• Dixit, Purnima; Tandon, J. P., Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 389 - 395
  作者：Dixit, Purnima、Tandon, J. P.

  DOI：——

  日期：——
• Srivastava, T. N.; Chauhan, A. K. S.; Agarwal, Manjula, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1980, vol. 10, p. 29 - 40
  作者：Srivastava, T. N.、Chauhan, A. K. S.、Agarwal, Manjula

  DOI：——

  日期：——
• Biological activities of pyridine-2-carbaldehyde Schiff bases derived from S-methyl- and S-benzyldithiocarbazate and their zinc(II) and manganese(II) complexes. Crystal Structure of the Manganese(II) complex of pyridine-2-carbaldehyde S-benzyldithiocarbazate
  作者：L. Z. Zhang、T. Ding、C. L. Chen、M. X. Li、D. Zhang、J. Y. Niu

  DOI：10.1134/s1070328411040117

  日期：2011.5

  Transition metal complexes [Zn(L-1)(2)] (I) and [Mn(L-2)(2)] (II), where HL1 = pyridine-2-carboxaldehyde S-methyldithiocarbazate, HL2 = pyridine-2-carboxaldehyde S-benzyldithiocarbazate, have been synthesized. Complex II was characterized by elemental analysis, IR spectra, and single-crystal X-ray diffraction studies. The manganese(II) atom in complex II adopts a distorted octahedral geometry with the Schiff base coordinated to it as a uninegatively charged tridentate chelating agent via the pyridine and azomethine nitrogen atoms and the thiolate sulfur atom. Biological studies carried out in vitro against selected bacteria, fungi, and K562 leukemia cell line, respectively, have shown that the free ligands and their metal complexes exhibited distinctive differences in the biological properties. Ligand HL1 and complex I have the marked and broad antimicrobial activities compared to HL2 and complex II while only HL1 and complex II show significant antitumor activity against K562 leukemia cell line, since they exhibit IC50 values in the mu M range.
• Synthesis and characterization of Zn(II) and Cd(II) complexes of S-benzyl-β-N-(2-pyridyl)methylenedithiocarbazate (HNNS): bioactivity of the HNNS Schiff base and its Zn(II), Cu(II) and Cd(II) complexes and the X-ray structure of the [Zn(NNS)2] complex
  作者：M.T.H Tarafder、A Kasbollah、K.A Crouse、A.M Ali、B.M Yamin、H.-K Fun

  DOI：10.1016/s0277-5387(01)00817-8

  日期：2001.8

  A tridentate Schiff base having HNNS donor sequence was prepared by condensing S-benzyldithiocarbazate (NH2NHCSSCH2Ph) with pyridine-2-carboxaldehyde. Complexes of this ligand, pyCHNNHCSSCH(2)Ph(HNNS), with Cu(II), Cd(II) and Zn(II) were synthesized and characterized by elemental analyses and various physico-chemical techniques. X-ray crystallographic analysis shows that the Zn(II) complex, [Zn(NNS)(2)], is six-coordinate and has a distorted octahedral structure with the ligand coordinated to the Zn(II) ion as a uninegatively charged tridentate chelating agent via the pyridine nitrogen, the azomethine nitrogen and the mercaptide sulfur atoms. Distortions from the regular octahedral geometry are attributed to the restricted bite angles of the planar NNS tridentate ligand. The Cu(II) complex, [Cu(NNS)CI], was paramagnetic with a square-planar stereochemistry while the Cd(II) complex, [Cd(NNS)Br], was diamagnetic and is suggested to have a tetrahedral structure. The Schiff base and its complexes were screened for antimicrobial, cytotoxic and antioxidant activities. Disc diffusion methods were employed for antimicrobial assays against eight pathogenic microorganisms. The Schiff base and the complexes do not display activities against any of the microorganisms. The Schiff base was cytotoxic with a CD50 value of 5.90 mug ml(-1) against the T-lymphoblastic leukemic cells while the Cu(II) and Cd(II) complexes were strongly cytotoxic with CD50 values of 2.20 and 2.30 mug ml(-1), respectively. The Cu(II) and Cd(II) complexes were also effective against colon cancer cells with CD50 values of 2.60 and 3.10 mug ml(-1), respectively. SBDTC showed a higher antioxidant activity than the alpha -tocopherol (vitamin E) and was comparable with butylated hydroxytoluene (BHT), a commercially used synthetic antioxidant. (C) 2001 Elsevier Science Ltd. All rights reserved.