silver(I) α-oximido-(ethylacetoxy)acetonitrile | 950847-32-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: silver(I) α-oximido-(ethylacetoxy)acetonitrile
• 英文别名: Ag(ECO)；α-Hydroximino-cyanessigsaeure-aethylester-Ag-Salz
• CAS: 950847-32-2
• 化学式: Ag*C₅H₅N₂O₃
• 分子量: 248.974
• InChiKey: OQIBJYPYHMMOCS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.01
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  silver(I) α-oximido-(ethylacetoxy)acetonitrile 以 neat (no solvent, solid phase) 为溶剂， 生成 银
  参考文献：
  名称：

  Light Insensitive Silver(I) Cyanoximates As Antimicrobial Agents for Indwelling Medical Devices

  摘要：

  Ten silver(I) cyanoximates of AgL composition (L = NC-C(NO)-R, where R is electron withdrawing groups: -CN, -C(O)NR2, -C(O)R' (alkyl), -C(O)OEt, 2-heteroaryl fragments such as 2-pyridyl, 2-benzimidazolyl, 2-benzoxazolyl, 2-benzthiazolyl) were synthesized and characterized using spectroscopic methods and X-ray analysis. Crystal structures of four complexes were determined and revealed the formation of two-dimensional (2D) coordination polymers of different complexity in which anions exhibit bridging or combined chelate and bridging binding modes. In these compounds, anions are in the nitroso form. All studied AgL complexes are sparingly soluble in water and are thermally stable to 150 degrees C Synthesized compounds demonstrated remarkable insensitivity toward visible light and UV-radiation, which was explained based on their polymeric structures with multiple covalent bonds between bridging cyanoxime ligands and Ag(I) centers. All 10 silver(I) cyanoximates were tested in vitro on the subject of their antimicrobial activity against both Gram-positive and Gram-negative microorganisms such as Escherichia coli, Klebsiella pneumoniae, Proteus sp., Pseudomonas aeruginosa, Enterococcus hirae, Streptococcus mutans, Staphylococcus aureus, and Mycobacterium fortuitum as well as against Candida albicans in solutions, and in the solid state as pressed pellets and dried filter paper disks presoaked with solutions of AgL in DMF. Results showed pronounced antimicrobial activity for all investigated complexes. A combination of five factors: (1) light insensitivity, (2) poor water solubility, (3) high thermal stability, (4) lack of toxicity of organic ligands, and (5) in vitro antimicrobial activity allows development of silver(I) cyanoximates for medical applications. These include antimicrobial additives to acrylate glue, cured by UV-radiation, used in introduction of prosthetic joints and dental implants, and prevention of biofilm formation on several types of indwelling medical devices.

  DOI：

  10.1021/ic100830x
• 作为产物：
  描述：

  silver nitrate 、 2-肟氰乙酸乙酯 在 potassium carbonate 作用下， 生成 silver(I) α-oximido-(ethylacetoxy)acetonitrile
  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

• Tin(IV) Cyanoximates:  Synthesis, Characterization, and Cytotoxicity
  作者：Nikolay Gerasimchuk、Tiffany Maher、Paul Durham、Konstantin V. Domasevitch、Janet Wilking、Andrew Mokhir

  DOI：10.1021/ic061354f

  日期：2007.9.1

  here attempts to combine the useful properties of both groups of compounds and investigate the likely antiproliferating activity of the new substances. A series of 19 organotin(IV) complexes, with nine different cyanoxime ligands, were anaerobically prepared by means of the heterogeneous metathesis reaction between the respective organotin(IV) halides (Cl, Br) and ML (M=Ag, Tl; L=cyanoximate anion), using

  近年来，许多有机锡（IV）衍生物对几种类型的癌症均表现出显着的细胞毒性。但是，含氰肟基有机锡（IV）配合物的性质是未知的。以前，已经显示出氰肟显示出有趣的生物活性谱，从生长调节到抗菌和农药的解毒作用。此处提出的工作试图结合两组化合物的有用特性，并研究新物质可能的抗增殖活性。通过相应的有机锡（IV）卤化物（Cl，Br）和ML（M = Ag，Tl; L =氰肟酸根阴离子），在室温下在CH3CN中使用超声波。使用光谱方法（紫外可见，IR，1H，13C NMR，119Sn Mossbauer）和X射线分析对化合物进行表征。配合物的晶体结构揭示了两种类型的氰基亚锡锡（IV）的形成：R4-xSnLx组成的单核五配位化合物（R = Me，Et，n-Bu，Ph; x = 1，2; L =氰肟酸根阴离子）和四核R8Sn4（OH）2O2L2物种（R = n-Bu，Ph）。后者的复合物包含一个平面的[Sn4（OH）2O2]
• Organoantimony(V) Cyanoximates:  Synthesis, Spectra and Crystal Structures
  作者：Konstantin V. Domasevitch、Nikolay N. Gerasimchuk、Andrew Mokhir

  DOI：10.1021/ic9906048

  日期：2000.3.1

  anions are bound to the antimony(V) atoms in a monodentate fashion via the oxygen atoms of the oxime groups. The ligands adopt trans-anti configuration in these compounds. The coordination polyhedron in both complexes is a distorted trigonal bipyramid with the axial location of the cyanoxime ligand. A similar binding mode of other anions in synthesized organoantimony(V) complexes has been offered on

  合成了一系列25种新的有机锑（V）氰基肟酸酯，并使用红外，可见光和NMR光谱以及X射线分析进行了研究。确定了化合物（C6H5）4Sb [ONC（CN）C（O）NH2]（1）和（ ）4Sb [ONC（CN）C（O）N（CH3）2]（2）的晶体结构。两种配合物均在单斜空间群P2（1）/ c（Z = 4）中结晶，其晶胞参数（A，grad）为a = 14.921（3），b = 10.165（2），c = 17.571（7），对于化合物1，β= 113.26（6），对于化合物2，a = 16.415（4），b = 10.406（3），c = 17.152（3），β= 17.152（3），β= 117.79（2）。通过5438和5056独立反射，细化分别为1和2的结构产生R系数0.022和0.037。氰肟酸阴离子通过肟基团的氧原子以单齿方式与锑（V）原子结合。这些化合物中的配体采用反式构型。两种
• Mokhir, A. A.; Gerasimchuk, N. N.; Pol'shin, E. V., Russian Journal of Inorganic Chemistry, 1994, vol. 39, p. 289 - 293
  作者：Mokhir, A. A.、Gerasimchuk, N. N.、Pol'shin, E. V.、Domasevich, K. V.

  DOI：——

  日期：——
• Synthesis and infrared and Mössbauer studies of Eu(III) complexes with cyanoxime anions
  作者：N. Gerasimchuk、E. Kuzmann、A. Büki、A. Vértes、L. Nagy、K. Burger

  DOI：10.1016/s0020-1693(00)80915-9

  日期：1991.10

  A series of europium(III) complexes with cyanoxime ligands were prepared. The IR spectroscopic data revealed that the ambidentate ligands were coordinated to the central europium(III) atom in either a tridentate or a bidentate manner. The Mossbauer isomer shift (IS) values showed a correlation with the quadrupole splitting (QS) values in all complexes. A plot of the IS values versus the QS values showed that with increasing electron density of the Eu(III) nucleus the symmetry of the electronic shell around the Eu(III) atom decreases.