5'-O-(N-(2-carbobenzyloxyaminobenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine | 873556-40-2

• 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-carbobenzyloxyaminobenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine
• 英文别名: benzyl N-[2-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxysulfonylcarbamoyl]phenyl]carbamate
• CAS: 873556-40-2
• 化学式: C₂₈H₂₉N₇O₉S
• 分子量: 639.646
• InChiKey: HWBZYCCPUDKXBO-RKCWLVDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  217
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5'-O-(N-(2-carbobenzyloxyaminobenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5'-O-(N-(2-aminobenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine
  参考文献：
  名称：

  Rationally Designed Nucleoside Antibiotics That Inhibit Siderophore Biosynthesis of Mycobacterium tuberculosis

  摘要：

  A rationally designed nucleoside inhibitor of Mycobacterium tuberculosis growth (MIC99 = 0.19 mu M) that disrupts siderophore biosynthesis was identified. The activity is due to inhibition of the adenylate-forming enzyme MbtA which is involved in biosynthesis of the mycobactins.

  DOI：

  10.1021/jm051060o
• 作为产物：
  描述：

  2-(((benzyloxy)carbonyl)amino)benzoic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 5'-O-(N-(2-carbobenzyloxyaminobenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine
  参考文献：
  名称：

  Rationally Designed Nucleoside Antibiotics That Inhibit Siderophore Biosynthesis of Mycobacterium tuberculosis

  摘要：

  A rationally designed nucleoside inhibitor of Mycobacterium tuberculosis growth (MIC99 = 0.19 mu M) that disrupts siderophore biosynthesis was identified. The activity is due to inhibition of the adenylate-forming enzyme MbtA which is involved in biosynthesis of the mycobactins.

  DOI：

  10.1021/jm051060o

文献信息

• Antibacterial Agents
  申请人：Aldrich Courtney

  公开号：US20080293666A1

  公开（公告）日：2008-11-27

  The invention provides compounds of formula (I) and salts thereof: R 1 -L-R 2 —B wherein R 1 , L, R 2 , and B have any of the values defined herein, as well as compositions comprising such compounds, and therapeutic methods comprising the administration of such compounds or salts. The compounds block siderophore production in bacteria and are useful as antibacterial agents.

  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。
• US7989430B2
  申请人：——

  公开号：US7989430B2

  公开（公告）日：2011-08-02
• Rationally Designed Nucleoside Antibiotics That Inhibit Siderophore Biosynthesis of <i>Mycobacterium </i><i>t</i><i>uberculosis</i>
  作者：Ravindranadh V. Somu、Helena Boshoff、Chunhua Qiao、Eric M. Bennett、Clifton E. Barry、Courtney C. Aldrich

  DOI：10.1021/jm051060o

  日期：2006.1.1

  A rationally designed nucleoside inhibitor of Mycobacterium tuberculosis growth (MIC99 = 0.19 mu M) that disrupts siderophore biosynthesis was identified. The activity is due to inhibition of the adenylate-forming enzyme MbtA which is involved in biosynthesis of the mycobactins.