5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2'-O-tert-butyldimethylsilyl-3'-deoxyadenosine triethylammonium salt | 939794-95-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2'-O-tert-butyldimethylsilyl-3'-deoxyadenosine triethylammonium salt
• 英文别名: [(2S,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]methyl N-(2-phenylmethoxybenzoyl)sulfamate;N,N-diethylethanamine
• CAS: 939794-95-3
• 化学式: C₆H₁₅N*C₃₀H₃₈N₆O₇SSi
• 分子量: 756.011
• InChiKey: YSADPGIOUWQIGB-ASZPXKOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2'-O-tert-butyldimethylsilyl-3'-deoxyadenosine triethylammonium salt 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 [(2S,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]methyl N-(2-hydroxybenzoyl)sulfamate;N,N-diethylethanamine
  参考文献：
  名称：

  Antibacterial Agents

  摘要：

  这项发明提供了化合物的公式(I)及其盐：R1-L-R2—B，其中R1、L、R2和B具有本文中定义的任何值，以及包含这种化合物的组合物，以及包含这种化合物或盐的治疗方法。这些化合物可以阻断细菌中的铁载体产生，并可用作抗菌剂。

  公开号：

  US20080293666A1

文献信息

• Antitubercular Nucleosides That Inhibit Siderophore Biosynthesis:  SAR of the Glycosyl Domain
  作者：Ravindranadh V. Somu、Daniel J. Wilson、Eric M. Bennett、Helena I. Boshoff、Laura Celia、Brian J. Beck、Clifton E. Barry、Courtney C. Aldrich

  DOI：10.1021/jm061068d

  日期：2006.12.1

  Tuberculosis is the leading cause of infectious disease mortality in the world by a bacterial pathogen. We previously demonstrated that a bisubstrate inhibitor of the adenylation enzyme MbtA, which is responsible for the second step of mycobactin biosynthesis, exhibited potent antitubercular activity. Here we systematically investigate the structure-activity relationships of the bisubstrate inhibitor glycosyl domain resulting in the identification of a carbocyclic analogue that possesses a K-I(app) value of 2.3 nM and MIC99 values of 1.56 mu M against M. tuberculosis H37Rv. The SAR data suggest the intriguing possibility that the bisubstrate inhibitors utilize a transporter for entry across the mycobacterial cell envelope. Additionally, we report improved conditions for the expression of MbtA and biochemical analysis, demonstrating that MbtA follows a random sequential enzyme mechanism for the adenylation half-reaction.