2-cyano-2-isonitrosothioacetamide | 50834-04-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-2-isonitrosothioacetamide
• 英文别名: 2-Cyano-2-hydroxyiminoethanethioamide
• CAS: 50834-04-3
• 化学式: C₃H₃N₃OS
• mdl: MFCD06245209
• 分子量: 129.142
• InChiKey: FBVPWNIBLBCCBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thallium(I) carbonate 、 2-cyano-2-isonitrosothioacetamide 以 水 为溶剂， 以3.781 g的产率得到
  参考文献：
  名称：

  Non-Antibiotic Antimony-Based Antimicrobials

  摘要：

  在室温下，利用固体 AgL（或 TlL）和 Sb(C6H5)4Br 在 CH3CN 中发生的高产异质偏合成反应，合成了一系列由 Sb(C6H5)4L 组成的八种新型有机锑(V)氰肟酸盐。氰肟酸 L 是根据其水溶性和以往的生物活性，从一大批 48 种已知肟类化合物中特别挑选出来的。合成的化合物在有机溶剂中的溶解性很好，并采用了多种常规光谱和物理方法对其进行了研究。测定了所有报告的有机金属化合物的晶体结构，发现锑原子形成了扭曲的三叉双锥环境，酸配体通过肟基团的 O 原子形成了单齿轴结合。这些化合物在固态和溶液分子化合物中都具有热稳定性。研究人员首次将这一系列专门设计的有机锑（V）化合物作为潜在的非抗生素抗菌剂，用于对抗三种细菌性和两种真菌性人类病原体。细菌病原体包括革兰氏阴性大肠杆菌和绿脓杆菌，以及革兰氏阳性金黄色葡萄球菌。真菌病原体包括新生隐球菌和白色念珠菌。单独的氰基亚胺没有抗菌效果，加入 SbPh4 基团后才有抗菌效果。总之，这些新的锑化合物显示出作为广谱和窄谱抗菌剂对付某些细菌和基底病原体的强大潜力，并为进一步合成修饰这些化合物以提高其活性提供了启示。

  DOI：

  10.3390/molecules27217171

文献信息

• First Bivalent Palladium and Platinum Cyanoximates:  Synthesis, Characterization, and Biological Activity
  作者：Daniel Eddings、Charles Barnes、Nikolay Gerasimchuk、Paul Durham、Konstantin Domasevich

  DOI：10.1021/ic0303439

  日期：2004.6.28

  A series of five cyanoximes (compounds having the general formula NC-C(=NOH)-R, where R is an amide or carboxylic ester group) have been synthesized and spectroscopically and structurally characterized. These are 2-cyano-2-isonitrosoacetamide (later HACO), 2-cyano-2-isonitrosothioacetamide (HTCO), 2-cyano-2-isonitrosoethylacetate (HECO), 2-cyano-2-isonitroso-N-piperidinylacetamide (HPiPCO), and 2-cyano-2-isonitroso-N-morpholinylacetamide (HMCO). A high yield method of synthesis was developed for the last two previously unknown amidocyanoximes. Variable temperature C-13 NMR studies in DMSO-d(6) solutions allowed the determination of rotational energy barriers for these two new cyanoximes. The HPiPCO and HMCO oxime molecules adopt a trans-anti configuration in the solid state according to X-ray analysis. Reactions between aqueous solutions of K+L- (L = cyanoximate anions: TCO-, PiPCO(-), and MCO-) and K-2[MCl4] (M = Pd, Pt) resulted in the formation of ML2 complexes. The crystal structure of Pd(MCO)(2).DMSO was determined and showed the formation of coplanar dimeric [Pd(MCO)]2 units with 3.13 Angstrom Pd...Pd separation. The complex adopts cis geometry with anions being in the nitroso form. In the presence of bivalent Pd and Pt, ACO(-) and ECO- anions completely or partially hydrolyze in aqueous solutions to the dianion of 2-cyano-2-isonitrosoacetic acid (AACO(2-)). The crystal structure of the product of the hydrolysis reaction, K-2[Pd(AACO)(2)].4H(2)O, was determined. Data revealed planar and cis geometry of the [Pd(AACO)(2)](2-) anion where cyanoximes are in the nitroso form and adopt a cis-anti configuration. All synthesized cyanoxime ligands and nine of their Pd(II) and Pt(II) complexes were tested in vitro on antiproliferating activity using human cervical cancer HeLa cell lines, and cisplatin as a positive control substance. Two out of the nine studied complexes, Pd(MCO)2 and Pt(MCO), were found to be active compounds inflicting death on 28% and 16% of the cells, respectively, with 55% value for the cisplatin under the same conditions.