S-(3-methylbenzyl)dithiocarbazate | 1255370-79-6

• 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: S-(3-methylbenzyl)dithiocarbazate
• 英文别名: S-3-methylbenzyldithiocarbazate
• CAS: 1255370-79-6
• 化学式: C₉H₁₂N₂S₂
• 分子量: 212.34
• InChiKey: PANWNAOSGKFPNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.05
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-(3-methylbenzyl)dithiocarbazate 以 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 Cu(S-3-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate)₂
  参考文献：
  名称：

  Synthesis, characterisation and biological activities of S-2- or S-4-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate and Cu(II), Ni(II), Zn(II) and Cd(II) complexes

  摘要：

  Metal complexes of general formula, [M(NNS)(2)] (M = Cu(II), Ni(II), Zn(II) and Cd(II); NNS' = S-2-methylbenzyl-beta-N-(di-2-pyridyl)methylenedithiocarbazate (1), NNS'' = S-3-methylbenzyl-beta-N-(di-2-pyridyl)methylenedithiocarbazate (2) and NNS''' = S-4-methylbenzyl-beta-N-(di-2-pyridyl)methylenedithiocarbazate (3) have been synthesized by reacting the respective metal acetates with the Schiff bases in an ethanol/acetonitrile mixture. They have been characterised by various physico-chemical techniques. Magnetic and spectral evidence indicate the formation of six-coordinate complexes in which the Schiff base coordinates as a uninegatively charged tridentate NNS ligand. The crystal structures of [Ni(NNS')(2)] (5), [Ni(NNS''')(2)] (13) and [Cd(NNS')(2]) (7) were solved via single-crystal X-ray crystallographic analysis. All three complexes possess a distorted octahedral geometry where two Schiff bases are coordinated to the central metal ion via the pyridine nitrogen-atom, the azomethine-nitrogen atom and the thiolate-sulphur atom; like donor atoms in the N4S2 donor set are mutually trans. The complexes have been assayed against selected pathogens and cancer cell lines. The complexes were inactive against all the fungal strains tested, but were mildly active against the bacterial strains tested, especially against Bacillus subtilis. Anti-microbial activity generally improved upon complexation with the transition metal ions. The Schiff bases and their transition metal complexes were mostly inactive against the examined cancer cell lines. The Schiff bases 13 were inactive against the MCF-7 (Human Breast cancer cells with positive estrogen receptor) and the MDA-MB-231 (Human Breast cancer cells with negative estrogen receptor) cell lines. Only 9 was active against MCF-7 whereas 10 and 13 were active against the MDA-MB-231 cell line. Cytotoxic activity was observed to be enhanced upon complexation particularly for the Ni(II) complexes. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.05.053
• 作为产物：
  描述：

  二硫化碳 、 3-甲基苄基氯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到S-(3-methylbenzyl)dithiocarbazate
  参考文献：
  名称：

  3-甲基苄基2-(6-甲基吡啶-2-基亚甲基)肼碳二硫酸酯及其过渡金属配合物的合成、表征和生物活性

  摘要：

  三齿氮硫席夫碱，3-甲基苄基 2-(6-甲基吡啶-2-基亚甲基)肼碳二硫酸酯 (6mpyS3M)，通过 6-甲基吡啶-2-醛与 S-3-甲基苄基二硫代氨基甲酸酯的缩合合成。它在空间群 P 21/n 中结晶。它在α-氮和吡啶基氮之间显示出分子间N-H···N氢键。硫酮硫在 C-N 键上相对于 6-甲基吡啶片段处于反式位置，但通过 C-S 键与 3-甲基苄基片段采用顺式位置。用 Cu(II)、Ni(II)、Zn(II) 和 Cd(II) 制备含有两个 6mpyS3M 配体的八面体配合物。针对选定的微生物和两种乳腺癌细胞系对 6mpyS3M 及其金属配合物进行了分析。6mpyS3M 对两种癌细胞系都具有很强的活性。它的金属配合物对 Cu(II)、Ni(II) 和 Zn(II) 配合物显示出高选择性，仅对一种癌细胞系具有强活性，而 Cd(II) 配合物仅对另一种具有强活性。只有 Cu(II) 和 Cd(II)

  DOI：

  10.1007/s11243-010-9406-6