2,5-去氢-1-O-(4-甲苯基磺酰基)甘露醇 | 84447-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-去氢-1-O-(4-甲苯基磺酰基)甘露醇
• 英文名称: 2,5-anhydro-1-O-(p-tolylsulfonyl)-D-mannitol
• 英文别名: 2,5-Anhydro-1-O-(4-tolylsulfonyl)mannitol；[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 84447-04-1
• 化学式: C₁₃H₁₈O₇S
• 分子量: 318.348
• InChiKey: PKVIFSOBCRKRCY-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-去氢-1-O-(4-甲苯基磺酰基)甘露醇 在 镍 sodium azide 、 氢气 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5
• 作为产物：
  描述：

  对甲苯磺酰氯 、 2,5-脱水-D-甘露醇 以 吡啶 为溶剂， 反应 18.0h， 生成 2,5-去氢-1-O-(4-甲苯基磺酰基)甘露醇
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5

文献信息

• Synthesis of some derivatives of 2,5-Anhydro-D-mannitol
  作者：RD Guthrie、ID Jenkins、JJ Watters、MW Wright、R Yamasaki

  DOI：10.1071/ch9822169

  日期：——

  The synthesis of 2,5:3,4-dianhydro-D-allitol and of a variety of derivatives (sulfonyloxy, deoxy, azido, iodo, etc.) of 2,5-anhydro-D-mannitol is described.

  合成 合成 2,5:3,4-二氢-D-异戊醇 和 2,5-anhydro-D-mannitol 的各种衍生物（磺酰氧基、脱氧、叠氮、碘等）的合成 脱氧、叠氮、碘等）的合成。 的各种衍生物（磺酰氧基、脱氧、叠氮、碘等）进行了描述。
• A simple O-sulfated thiohydroximate molecule to be the first micromolar range myrosinase inhibitor
  作者：Deimante Cerniauskaite、Estelle Gallienne、Henreta Karciauskaite、Andrea S.F. Farinha、Jolanta Rousseau、Sylvie Armand、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/j.tetlet.2009.02.072

  日期：2009.7

  New non-hydrolyzable analogues of glucosinolates have been prepared. Myrosinase inhibition was observed with modified aglycon moieties, even bulky phenothiazine analogue 6 gave reasonable inhibition. The simplest structure 8 derived from dimethylaminoethanethiol has shown to be the most potent inhibitor with an IC50 of 3.32 mu M. (C) 2009 Elsevier Ltd. All rights reserved.