S-(2-methylbenzyl)dithiocarbazate | 34930-10-4

• 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-(2-methylbenzyl)dithiocarbazate
• 英文别名: S-2-methylbenzyl dithiocarbazate；S-2-methylbenzyl-dithiocarbazate；S-2-methylbenzyldithiocarbazate；hydrazinecarbodithioic acid 2-methyl-benzyl ester；o-Methylbenzyl-dithiocarbazinat
• CAS: 34930-10-4
• 化学式: C₉H₁₂N₂S₂
• 分子量: 212.34
• InChiKey: CRYLWWQEUWOVGO-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-(2-methylbenzyl)dithiocarbazate 以 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 Zn(S-2-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：

  dithiocarbonic acid hydrazide 、 邻甲基氯化苄 以 乙醇 为溶剂， 生成 S-(2-methylbenzyl)dithiocarbazate
  参考文献：
  名称：

  Synthesis, Characterisation and Biological Activities of 2-Methylbenzyl 2-(dipyridin-2-yl methylene)hydrazinecarbodithioate

  摘要：

  通过二-2-吡啶基酮和新型二硫代氨基甲酸酯 S-2-甲基苄基-二硫代氨基甲酸酯 (S2MBDTC) 的缩合合成了一种新的三齿氮硫希夫碱。使用各种物理化学和光谱技术对希夫碱进行了表征。报道了席夫碱的 X 射线晶体学分析。席夫碱在空间群为 P 21/n 的单斜晶系中结晶，晶胞参数 a = 10.8128 (2) Å, b = 9.3832 (2) Å, c = 18.0352 (4) Å, β = 97.1311 ( 9)°。希夫碱被发现对选定的微生物和两种乳腺癌细胞系（MCF-7 = 具有阳性雌激素受体的人乳腺癌细胞系，MDA-MB-231 = 具有阴性雌激素受体的人乳腺癌细胞系）没有活性。

  DOI：

  10.1007/s10870-010-9907-3

文献信息

• Unusual saccharin-N,O (carbonyl) coordination in mixed-ligand copper(II) complexes: Synthesis, X-ray crystallography and biological activity
  作者：Nur Shuhada Mohd Mokhtaruddin、Enis Nadia Md Yusof、Thahira B.S.A. Ravoof、Edward R.T. Tiekink、Abhi Veerakumarasivam、Mohamed Ibrahim Mohamed Tahir

  DOI：10.1016/j.molstruc.2017.03.037

  日期：2017.7

  azomethine-nitrogen and thiolate-sulphur atoms. Magnetic data indicated a square pyramidal environment for the complexes and the conductivity values showed that the complexes were essentially non-electrolytes in DMSO. The X-ray crystallographic analysis of one complex, [Cu(sac)(S2AP)]2 showed that the Cu(II) atom was coordinated to the thiolate-S, azomethine-N and pyridyl-N donors of the S2AP Schiff base and

  摘要 通过S-2-甲基苄基二硫代氨基甲酸酯与2-乙酰基-4-甲基吡啶(S2APH)的缩合反应合成了三种含有N和S供体原子的三齿席夫碱；4-甲基-3-氨基硫脲与 2-乙酰基吡啶 (MT2APH) 和 4-乙基-3-氨基硫脲与 2-乙酰基吡啶 (ET2APH)。然后合成了三种具有通式 [Cu(sac)(L)]2（sac = 糖精阴离子；L = 席夫碱的阴离子）的新型双核混合配体铜 (II) 配合物，并随后表征为红外和紫外/可见光谱以及摩尔电导率和磁化率测量。席夫碱还使用 NMR 和 MS 进行光谱表征，以进一步确认其结构。光谱数据表明，席夫碱表现为通过吡啶基-氮、偶氮甲碱-氮和硫醇盐-硫原子配位的三齿 NNS 供体配体。磁性数据表明复合物为方形金字塔环境，电导率值表明复合物在 DMSO 中基本上是非电解质。一种复合物 [Cu(sac)(S2AP)]2 的 X 射线晶体学分析表明，Cu(II) 原子与
• o-Vanillin Derived Schiff Bases and Their Organotin(IV) Compounds: Synthesis, Structural Characterisation, In-Silico Studies and Cytotoxicity
  作者：Enis Nadia Md Yusof、Muhammad A. M. Latif、Mohamed I. M. Tahir、Jennette A. Sakoff、Michela I. Simone、Alister J. Page、Abhi Veerakumarasivam、Edward R. T. Tiekink、Thahira B. S. A. Ravoof

  DOI：10.3390/ijms20040854

  日期：——

  diffraction. The organotin(IV) compounds were synthesised from the reaction of Ph₂SnCl₂ or Me₂SnCl₂ with the Schiff bases (S2MoVaH/S4MoVaH/SBoVaH) to form a total of six new organotin(IV) compounds that had a general formula of [R₂Sn(L)] (where L = Schiff base; R = Ph or Me). The molecular geometries of Me₂Sn(S2MoVa), Me₂Sn(S4MoVa) and Me₂Sn(SBoVa) were established by X-ray crystallography and verified

  合成了由SR-二硫代氨基甲酸酯[R =苄基（B），2-或4-甲基苄基（分别为2M和4M）]与2-羟基-3-甲氧基苯甲醛（oVa）缩合而​​成的6种席夫碱的新有机锡（IV）化合物通过元素分析，各种光谱技术（包括红外，紫外可见，多核（1 H，13 C，119Sn）NMR和质谱法以及单晶X射线衍射）合成并表征。由Ph 2 SnCl 2或Me 2 SnCl 2与席夫碱（S2MoVaH / S4MoVaH / SBoVaH）反应合成有机锡（Ⅳ）化合物，以形成总共六个新的通式为［R 2 Sn（L）］的有机锡（Ⅳ）化合物。 （其中L = Schiff碱； R = Ph或Me）。用X射线晶体学确定了Me 2 Sn（S 2 MoVa），Me 2 Sn（S 4 MoVa）和Me 2 Sn（SBoVa）的分子几何结构，并用密度泛函理论计算进行了验证。有趣的是，每个实验结构在晶体学不对称单元中均包含两个独立但化学
• Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies
  作者：Enis Nadia Md Yusof、Muhammad A.M. Latif、Mohamed I.M. Tahir、Jennette A. Sakoff、Abhi Veerakumarasivam、Alister J. Page、Edward R.T. Tiekink、Thahira B.S.A. Ravoof

  DOI：10.1016/j.molstruc.2019.127635

  日期：2020.4

  analysis, FT-IR and multinuclear NMR (1H, 13C and 119Sn) spectroscopy. The crystal structures of tin(IV) [S-4-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene)dithiocarbazate] (2) and tin(IV) [S-benzyl-β-N-(2-hydroxy-3-methoxy benzylmethylene)dithiocarbazate] (3) were determined by X-ray single crystal diffraction analysis. X-ray crystallography showed the molecular geometries in homoleptic 2 and 3

  摘要 六种新的锡 (IV) 化合物源自三齿二负电荷 ONS 二硫代氨基甲酸酯席夫碱，源自 2-羟基-3-甲氧基苯甲醛（H2L1、H2L2 和 H2L3）和 2,3-二羟基苯甲醛（H2L4、H2L5 和 H2L6）（其中 H2Ln =席夫碱的二酸）报道。通过元素分析、FT-IR 和多核 NMR（1H、13C 和 119Sn）光谱对化合物进行表征。锡(IV) [S-4-甲基苄基-β-N-(2-羟基-3-甲氧基苄亚甲基)二硫代氨基甲酸酯] (2) 和锡(IV) [S-苄基-β-N-(2-羟基-3-甲氧基苄基亚甲基)二硫代氨基甲酸酯](3)通过X射线单晶衍射分析测定。X 射线晶体学显示均配体 2 和 3 中的分子几何形状非常相似，其中二负性三齿配体通过硫醇盐-S 与锡原子配位，苯氧化物-O 和亚胺-N 原子。配位几何是基于一个八面体，具有相同的原子相互反式。实验结果通过 B3LYP/LanL2DZ/6-311G(d
• Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases
  作者：Enis Nadia Md. Yusof、Nurul N. M. Ishak、Muhammad A. M. Latif、Mohamed I. M. Tahir、Jennette A. Sakoff、Alister J. Page、Edward R. T. Tiekink、Thahira B. S. A. Ravoof

  DOI：10.1007/s11164-020-04095-x

  日期：2020.4

  Abstract A series of tridentate ONS Schiff bases were synthesised via condensation by reacting 2,3-dihydroxybenzaldehyde with S-2-methylbenzyldithiocarbazate (S2MBDTC) (1), S-4-methylbenzyldithiocarbazate (S4MBDTC) (2) and S-benzyldithiocarbazate (SBDTC) (3) in an equimolar ratio (10 mmol). The Schiff bases were then reacted with diphenyltin(IV) and dimethyltin(IV) dichloride in an equimolar ratio (1 mmol)

  摘要 通过使2,3-二羟基苯甲醛与S-2-甲基苄基二硫代咔唑酸酯（S2MBDTC）（1），S-4-甲基苄基二硫代咔唑酸酯（S4MBDTC）（2）和S-苄基二硫代咔唑酸酯（SBDTC）（3）以等摩尔比（10mmol）。然后使席夫碱与二苯基锡（IV）和二氯化二甲基锡（IV）以等摩尔比（1 mmol）反应，生成六种新的有机锡（IV）化合物（4 – 9）。所有化合物均通过元素分析，FT-IR，多核NMR，UV-Vis，质谱和摩尔电导率成功表征。对于五种化合物，分子几何结构3，5，6，8和9，已经通过X射线晶体学确定。每个二有机锡分子的五坐标几何结构由锡键合取代基中的两个碳原子以及衍生自负三齿二硫代氨基甲酸酯配体的三个供体原子定义，即硫醇盐-S，酚盐-O和亚胺基-N原子。所得的五坐标C 2 NOS几何形状介于理想的方形金字塔形和三角形双锥体几何形状之间。的二苯基（IV）的化合物（4 - 6）表现出特
• Synthesis, characterisation and structure determination of 3-[(1Z)-{2-[bis({[(2-methylphenyl)methyl]sulfanyl})methylidene]hydrazin-1-ylidene}methyl]benzene-1,2-diol
  作者：Enis Nadia Md Yusof、Edward R.T. Tiekink、Mukesh M. Jotani、Michela I. Simone、Alister J. Page、Thahira B.S.A. Ravoof

  DOI：10.1016/j.molstruc.2018.06.013

  日期：2018.11

  Abstract A light-yellow crystalline product (1), which was isolated after one week from the filtrate of the reaction between S-2-methylbenzyldithiocarbazate and 2,3-dihydroxybenzaldehyde, was characterised by single crystal X-ray diffraction, FTIR and NMR spectroscopic analyses. The experimental molecular structure of 1 has been established by X-ray crystallography and showed, to a first approximation

  摘要 S-2-甲基苄基二硫代氨基甲酸酯与2,3-二羟基苯甲醛反应1周后，经单晶X射线衍射、红外光谱和核磁共振光谱表征，分离得到淡黄色结晶产物(1)。分析。1 的实验分子结构已通过 X 射线晶体学确定，并显示出平面 C2N2S2 + 二羟基苯基区域，该区域与侧链 S 键合苄基的环几乎呈正交关系。这种结构已通过密度泛函理论计算得到验证，使用 B3LYP/6311G(d,p) 理论水平。分子堆积沿 b 轴呈线性超分子链，由甲苯基-C H…N(亚胺)和甲苯基-C H…π(甲苯基)相互作用维持；