1-(2-hydroxyethyl)-3,7,9-trimethylxanthin-8-ylidene silver acetate | 1092117-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2-hydroxyethyl)-3,7,9-trimethylxanthin-8-ylidene silver acetate
• CAS: 1092117-10-6
• 化学式: C₁₂H₁₇AgN₄O₅
• 分子量: 405.159
• InChiKey: HJKHTWLYJAZTNF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.57
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.01
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  可可碱 以 甲醇 为溶剂， 反应 2.0h， 生成 1-(2-hydroxyethyl)-3,7,9-trimethylxanthin-8-ylidene silver acetate
  参考文献：
  名称：

  Synthesis and anticancer activity of silver(i)–N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine

  摘要：

  从天然黄嘌呤产品中提取的银-N-杂环卡宾络合物已经制备完成。化学敏感性研究表明，细胞毒性、配体立体效应和亲水性之间存在相关性。

  DOI：

  10.1039/c4dt03679d

文献信息

• A theobromine derived silver N-heterocyclic carbene: synthesis, characterization, and antimicrobial efficacy studies on cystic fibrosis relevant pathogens
  作者：Matthew J. Panzner、Khadijah M. Hindi、Brian D. Wright、Jane B. Taylor、Daniel S. Han、Wiley J. Youngs、Carolyn L. Cannon

  DOI：10.1039/b907726j

  日期：——

  The increasing incidence of multidrug-resistant (MDR) pulmonary infections in the cystic fibrosis (CF) population has prompted the investigation of innovative silver based therapeutics. The functionalization of the naturally occurring xanthine theobromine at the N1 nitrogen atom with an ethanol substituent followed by the methylation of the N9 nitrogen atom gives the N-heterocyclic carbene precursor 1-(2-hydroxyethyl)-3,7,9-trimethylxanthinium iodide. The reaction of this xanthinium salt with silver acetate produces the highly hydrophilic silver carbene complex SCC8. The in vitro antimicrobial efficacy of this newly synthesized complex was evaluated with excellent results on a variety of virulent and MDR pathogens isolated from CF patients. A comparative in vivo study between the known caffeine derived silver carbene SCC1 and SCC8 demonstrated the ability of both complexes to improve the survival rates of mice in a pneumonia model utilizing the clinically isolated infectious strain of Pseudomonas aeruginosa PA M57-15.

  囊性纤维化（CF）人群中耐多药（MDR）肺部感染的发病率不断增加，促使人们对创新的银基疗法进行研究。天然存在的黄嘌呤可可碱在 N1 氮原子处被乙醇取代基官能化，随后 N9 氮原子甲基化，得到 N-杂环卡宾前体 1-(2-羟乙基)-3,7,9-三甲基碘化黄嘌呤。这种黄嘌呤盐与乙酸银反应生成高度亲水性的卡宾银络合物 SCC8。这种新合成的复合物的体外抗菌功效经过评估，对从 CF 患者中分离出的多种剧毒和 MDR 病原体具有优异的结果。已知的咖啡因衍生银卡宾 SCC1 和 SCC8 之间的比较体内研究表明，两种复合物能够提高使用临床分离的铜绿假单胞菌 PA M57-15 感染菌株的肺炎模型中小鼠的存活率。