Ag(BOCO) | 1252665-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: Ag(BOCO)
• 英文别名: 2-(oximido)-2-benzoxazoleacetonitrile silver(I)
• CAS: 1252665-96-5
• 化学式: Ag*C₉H₄N₃O₂
• 分子量: 294.018
• InChiKey: CDUWVXVRXKBZLJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.24
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Ag(BOCO) 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：

  N-hydroxybenzo[d]oxazole-2-carbimidoyl cyanide 、 silver nitrate 以 乙醇 、 水 为溶剂， 以98%的产率得到Ag(BOCO)
  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

文献信息

• Light Insensitive Silver(i) Cyanoximates As Antimicrobial Agents For Indwelling Medical Devices
  申请人：Gerasimchuk Nikolay

  公开号：US20130096098A1

  公开（公告）日：2013-04-18

  Silver(I) cyanoximates of AgL composition (L=NC—C(NO)—R, where R is electron withdrawing groups: —CN, —C(O)NR 2 , —C(O)R′ (alkyl), —C(O)OEt, 2-heteroaryl fragments such as 2-pyridyl, 2-benzimidazolyl, 2-benzoxazolyl, 2-benzthiazolyl) are synthesized and characterized using spectroscopic methods and X-ray analysis. The synthesized compounds also demonstrate remarkable insensitivity toward visible light and UV-radiation. The combined characteristics of these compounds, such as light insensitivity, poor water solubility, high thermal stability, lack of toxicity of organic ligands, and antimicrobial activity make these silver(I) cyanoximates compounds suitable for use in biomaterial and medical devices.

  本研究合成并使用光谱方法和X射线分析表征了AgL配合物（其中L=NC—C(NO)—R，R为电子吸引基团：—CN，—C（O）NR2，—C（O）R'（烷基），—C（O）OEt，2-杂环芳基片段，如2-吡啶基，2-苯并咪唑基，2-苯并噁唑基，2-苯并噻唑基）。合成的化合物还表现出对可见光和紫外辐射的显著不敏感性。这些化合物的综合特性，如光不敏感性，水溶性差，高热稳定性，有机配体的无毒性和抗微生物活性，使得这些银（I）氰酰肟化合物适用于生物材料和医疗器械。