N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride | 82655-59-2

• 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: N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride
• 英文别名: N-(diethylaminothiocarbonyl)benzimidoyl chloride；N-(Diethylcarbamothioyl)benzenecarboximidoyl chloride；N-(diethylcarbamothioyl)benzenecarboximidoyl chloride
• CAS: 82655-59-2
• 化学式: C₁₂H₁₅ClN₂S
• 分子量: 254.784
• InChiKey: YCBRCZVTEVYHGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.25h， 生成
  参考文献：
  名称：

  Ni(II), Pd(II) and Cu(II) complexes with N-(dialkylthiocarbamoyl)-N′-picolylbenzamidines: Structure and activity against human MCF-7 breast cancer cells

  摘要：

  N-(Dialkylthiocarbamoyl)-N'-picolylbenzamidines (HLEt and HLMorph) react with NiCl2, CuCl2 and [PdCl2(MeCN)(2)] with the formation of complexes of the general composition [M(L-R)Cl] (M = Ni (1), Pd (2)) and the dimeric complexes [{Cu(L-R)Cl}(2)] (3). The molecular structures of complexes 1 and 2 exhibit a square-planar coordination sphere, in which the organic ligands coordinate in a S,N,N coordination mode. The two subunits of 3, the arrangement of each is similar to those of 1 and 2, are connected via two weak Cu-Cl' bonds. The copper complexes [(Cu(L-R)Cl)(2)] (3) are slowly oxidized under aerobic conditions to give [{Cu(*L-R)Cl)(2)] complexes (4), where H*L-R = N-(dialkylthiocarbamoyl)-N'-picolinoyl-benzamidines. Complexes 1 and 2 show a very weak reduction of the growth of human MCF-7 breast cancer cells. Complexes 4, however, possess a remarkable cytotoxicity with IC50 values within the range 0.40-1.05 mu M. Compounds 3 are likely converted to 4 under the conditions of the cytotoxicity assay, and consequently exhibit IC50 values very similar to those found for 4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.08.088
• 作为产物：
  描述：

  在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride
  参考文献：
  名称：

  氟化苯甲酰硫脲衍生的硫代氨基脲和噻二嗪：合成，晶体结构和抗克氏锥虫活性

  摘要：

  通过将卤化的N-（二乙基氨基硫代羰基）苯甲酰氯（3b–3h）与4,4-二甲基-3-硫代氨基脲缩合，可获得一系列的硫代氨基脲。评估了卤代化合物对寄生虫克氏锥虫的活性，并将其与先前报道的相应的未取代的硫代半脲的活性进行了比较。发现在大多数情况下卤素取代增强了抗寄生虫活性。所述元-fluorinated化合物（4克）被确定为最有效的一个（IC 50 = 9.0μM，CC 50 > 200μM），具有选择性指数（SI = IC 50 / CC 50），比未取代的化合物高4倍。合成某些苯甲酰硫脲3a-3g所用反应条件的轻微改变导致意外形成了新型卤代6-氨基-1,3,5-噻二嗪-2-硫酮。

  DOI：

  10.1016/j.jfluchem.2018.08.004

文献信息

• Propargyl‐Substituted Thiocarbamoylbenzamidines of Technetium and Rhenium: Steps towards Bioconjugation with Use of Click Chemistry
  作者：Juan Daniel Castillo Gomez、Adelheid Hagenbach、Ulrich Abram

  DOI：10.1002/ejic.201601039

  日期：2016.12

  were analyzed by NMR, IR, and mass spectrometry as well as by X-ray diffraction. A similar coupling procedure has been applied for an azido-modified angiotensin-II peptide, which gives the desired rhenium(V) bioconjucate with good yields. The ease of this coupling and the stability of the conjugate recommends such tetradentate thiocarbamoylbenzamidines also for clinically relevant bioconjugates with

  摘要：合成了一种新的炔丙基取代的硫代氨基甲酰基苯甲脒。该化合物作为四齿配体并与 ReVO}3+ 和 TcVO}3+ 核形成稳定的复合物。所得配合物与苄基叠氮化物的“点击”偶联产生原型三唑衍生物，通过 NMR、IR、质谱以及 X 射线衍射对其进行分析。类似的偶联程序已应用于叠氮修饰的血管紧张素 II 肽，它以良好的产率提供所需的铼 (V) 生物偶联物。这种偶联的简易性和偶联物的稳定性推荐此类四齿硫代氨基甲酰基苯甲脒也用于具有 99mTc 的临床相关生物偶联物。
• The formation of tetrameric oxotechnetium(V) and oxorhenium(V) complexes by cyclisation of a potentially multidentate thiocarbohydrazide derivative
  作者：Dirk Hauenstein、Ulrich Abram

  DOI：10.1016/j.inoche.2011.04.037

  日期：2011.8

  Abstract Tetrameric complexes of the composition [MO(L1)]4 (M = Tc, Re), where (L1)3– represents an asymmetric, trianionic cyclisation product with thiocarbamoylbenzamidinato and mercaptotriazolato donor sites, were formed during reactions of [TcOCl4]– or [ReOCl4]– with a potentially multidentate ligand derived from thiocarbohydrazide and N-[N',N'-diethylamino(thiocarbonyl)]benzimidoyl chloride.

  摘要 组成 [MO(L1)]4 (M = Tc, Re) 的四聚体配合物是在 [TcOCl4]-或 [ReOCl4]– 具有衍生自硫代碳酰肼和 N-[N',N'-二乙氨基（硫代羰基）]苯甲酰氯的潜在多齿配体。
• Rhenium(V) complexes with tridentate P,N,S ligands
  作者：Jennifer Schroer、Ulrich Abram

  DOI：10.1016/j.poly.2011.11.023

  日期：2012.2

  ligands with P,N,S donor sets (HLdiethyl and HLmorph) were prepared from reactions of N-(dialkyl)thiocarbamoylbenzimide chlorides with 2-(diphenylphosphinomethyl)aniline. They readily react with (NBu4)[ReOCl4] under formation of air-stable [ReOCl2(LR)] complexes, in which the tridentate ligands coordinate meridionally. A similar coordination mode is observed in the nitridorhenium(V) complex [ReN(OReO3)(PPh3)(Ldiethyl)]

  摘要由N-（二烷基）硫代氨基甲酰基苯甲酰氯与2-（二苯基膦基甲基）苯胺反应制得了具有P，N，S供体对的新型潜在三齿配体（HLdiethyl和HLmorph）。它们很容易与（NBu4）[ReOCl4]反应，形成空气稳定的[ReOCl2（LR）]络合物，其中三齿配体在子午线上进行配位。在氮化or（V）络合物[ReN（OReO3）（PPh3）（Ldiethyl）]中观察到类似的配位模式，可以从[ReNCl2（PPh3）2]与HLdiethyl的反应中获得。配合物通过光谱和X射线结构分析来表征。
• C-S Bond Cleavage during Reactions between N,N-Diethylthiocarbamoyliminothianes and [MOCl4]- Complexes (M = Re, Tc)
  作者：Dirk Hauenstein、Adelheid Hagenbach、Ulrich Abram

  DOI：10.1002/zaac.201100359

  日期：2011.10

  [MOCl4]– complexes (M = Re, Tc) react with thianes derived from N-[(diethylamino)(thiocarbonyl)]benzamidoyl chloride and 2-mercaptophenol (HL1) and 2-mercaptoaniline (HL2) under C–S bond cleavage and formation of oxorhenium(V) and oxotechnetium(V) complexes with the resulting decomposition products 2-mercaptophenol and N-[(dialkylamino)thiocarbonyl]-N′-2-mercaptophenyl)benzamidine (H2L2a), respectively

  [MOCl4]– 配合物 (M = Re, Tc) 与衍生自 N-[(二乙氨基)(硫代羰基)]苯甲酰氯和 2-巯基苯酚 (HL1) 和 2-巯基苯胺 (HL2) 的硫烷在 C-S 键断裂下反应，并分别与所得分解产物 2-巯基苯酚和 N-[（二烷基氨基）硫代羰基]-N'-2-巯基苯基）苯甲脒（H2L2a）形成氧铼（V）和氧锝（V）络合物。产物 (NBu4)[ReO(S,O-C6H4)2]、[ReOCl(L2a)] 和 [TcO(L2a)] 以良好的收率获得并以结晶形式分离。单晶 X 射线研究揭示了正在研究的所有三种产品复合物都具有顶端氧配体的方形锥体配位环境。
• Nickel(<scp>ii</scp>) and copper(<scp>ii</scp>) complexes constructed with N₂S₂ hybrid benzamidine–thiosemicarbazone ligand: synthesis, X-ray crystal structure, DFT, kinetico-catalytic and in vitro biological applications
  作者：Paranthaman Vijayan、Periasamy Viswanathamurthi、Krishnaswamy Velmurugan、Raju Nandhakumar、Manickam Dakshinamoorthi Balakumaran、Pudupalayam Thangavelu Kalaichelvan、Jan Grzegorz Malecki

  DOI：10.1039/c5ra18568h

  日期：——

  We report nickel(ii) and copper(ii) complexes containing the benzamidine–thiosemicarbazone ligand together with DFT, enzyme kinetics and in vitro biological applications such as DNA/BSA affinities and anticancer properties.

  我们报告了含苯甲酰胺基-硫脲酮配体的镍（II）和铜（II）配合物，同时结合DFT、酶动力学和体外生物学应用，如DNA/BSA亲和力和抗癌性能。