pyrazol-1-yl dithiocarbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: pyrazol-1-yl dithiocarbamate
• 英文别名: pyrazol-1-yldithiocarbamate；pyrazole-1-carbodithioic acid；Pyrazole-1-carbonodithioic acid
• 化学式: C₄H₄N₂S₂
• 分子量: 144.221
• InChiKey: DKAXJCMDDSISHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三苯基膦氯金 、 pyrazol-1-yl dithiocarbamate 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以93%的产率得到pyrazolyl-1-dithiocarbamato-triphenylphosphinogold(I)
  参考文献：
  名称：

  Phosphinogold(I) Dithiocarbamate Complexes: Effect of the Nature of Phosphine Ligand on Anticancer Properties

  摘要：

  The reactions of potassium salts of the dithiocarbamates L {where L = pyrazolyldithiocarbamate (L1), 3,5-dimethylpyrazolyldithiocarbamate (L2), or indazolyldithiocarbamate (L3)} with the gold precursors [AuCl(PPh3)], [Au2Cl2(dppe)], [Au2Cl2(dppp)], or [Au2Cl2-(dpph)] lead to the new gold(I) complexes [AuL(PPh3)] (1-3), [Au2L2(dppe)] (4-6), [(Au2L2)(dppp)] (7-9), and [Au-2(L)(2)(dpph)] (10-12) {where dppe = 1,2-bis(diphenylphosphino)ethane, dppp = 1,3-bis(diphenylphosphino)propane, and dpph = 1,6-bis-(diphenylphosphino)hexane}. These gold compounds were characterized by a combination of NMR and infrared spectroscopy, microanalysis, and mass spectrometry; and in selected cases by single-crystal X-ray crystallography. Compounds 4-6, which have dppe ligands, are unstable in solution for prolonged periods, with 4 readily transforming to the Au-18 cluster [Au18S8(dppe)(6)]Cl-2 (4a) in dichloromethane. Compounds 1-3 and 7-12 are all active against human cervical epithelioid carcinoma (HeLa) cells, but the most active compounds are 10 and 11, with IC50 values of 0.51 mu M and 0.14 mu M, respectively. Compounds 10 and 11 are more selective toward HeLa cells than they are toward normal cells, with selectivities of 25.0 and 70.5, respectively. Further tests, utilizing the 60-cell-line Developmental Therapeutics Program at the National Cancer Institute (U.S.A.), showed 10 and 11 to be active against nine other types of cancers.

  DOI：

  10.1021/ic4025926

文献信息

• N-heterocyclic dithiocarbamate platinum(II) complexes: Unexpected transformation of dithiocarbamate to oxodithiocarbonate in phosphinoplatinum complexes in solution
  作者：Frankline K. Keter、Ilia A. Guzei、James Darkwa

  DOI：10.1016/j.inoche.2012.10.003

  日期：2013.1

  [PtCl2(dppe)] (dppe=1,2-bis(diphenylphosphino)ethane) reacts with pyrazol-1-yl- (L1), 3,5-dimethylpyrazol-1-yl- (L2), and indazol-1-yl- (L3) dithiocarbamate to form (Pt(L1)(2)(dpPe)1 (1), [Pt(L2)(2)(dPPe)] (2) and [Pt(L3)(2)(dppe)] (3). These complexes readily transform into [Pt(S2CO)(dppe)] (4) in chloroform and dichloromethane at room temperature. Stability of the bis(dithiocarbamate)platinum complex from L2, [Pt(L2)(2)] (5) suggests that the transformation of 1-3 to 4 is facilitated by the phosphine ancillary ligand. (C) 2012 Elsevier B.V. All rights reserved.