methyl 5-deoxy-5-butylthio-α-D-arabinofuranoside | 1038463-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-deoxy-5-butylthio-α-D-arabinofuranoside
• 英文别名: (2S,3S,4S,5S)-2-(butylsulfanylmethyl)-5-methoxyoxolane-3,4-diol
• CAS: 1038463-32-9
• 化学式: C₁₀H₂₀O₄S
• 分子量: 236.332
• InChiKey: DUIJDEXDYUFRFE-IMSYWVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丁硫醇 、 methyl 5-O-p-toluenesulfonyl-α-D-arabinofuranoside 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到methyl 5-deoxy-5-butylthio-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of methyl 5-S-alkyl-5-thio-d-arabinofuranosides and evaluation of their antimycobacterial activity

  摘要：

  The emergence of drug resistant tuberculosis necessitates a search for new antimycobacterial compounds. The antigen 85 (ag85) complex is a family of mycolyl transferases involved in the synthesis of trehalose-6,6'-dimycolate and the mycolated hexasaccharide motif found at the terminus of the arabinogalactan in mycobacterium. Enzymes involved in the synthesis of cell wall structures like these are potential targets for the development of new antiinfectives. To potentially inhibit the ag85 complex, methyl 5-S-alkyl-5-thio-arabinofuranoside analogues were designed based on docking studies with ag85C derived from Mycobacterium tuberculosis. The target arabinofuranosides were then synthesized and the antibacterial activity evaluated against Mycobacterium smegmatis ATCC 14468. Two of the compounds, 5-S-octyl-5-thio-alpha-D-arabinofuranoside (8) and 5-S-octyl-5-thio-beta-D-arabinofuranoside (11), showed MICs of 256 and 512 mu g/mL, respectively. Attempts to directly evaluate acyltransferase inhibitory activity of the arabinofuranosides against ag85C are also described. In conclusion, a new class of antimycobacterial arabinofuranosides has been discovered. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.03.062

文献信息

• Synthesis of methyl 5-S-alkyl-5-thio-d-arabinofuranosides and evaluation of their antimycobacterial activity
  作者：Aditya K. Sanki、Julie Boucau、Parijat Srivastava、Samuel S. Adams、Donald R. Ronning、Steven J. Sucheck

  DOI：10.1016/j.bmc.2008.03.062

  日期：2008.5

  The emergence of drug resistant tuberculosis necessitates a search for new antimycobacterial compounds. The antigen 85 (ag85) complex is a family of mycolyl transferases involved in the synthesis of trehalose-6,6'-dimycolate and the mycolated hexasaccharide motif found at the terminus of the arabinogalactan in mycobacterium. Enzymes involved in the synthesis of cell wall structures like these are potential targets for the development of new antiinfectives. To potentially inhibit the ag85 complex, methyl 5-S-alkyl-5-thio-arabinofuranoside analogues were designed based on docking studies with ag85C derived from Mycobacterium tuberculosis. The target arabinofuranosides were then synthesized and the antibacterial activity evaluated against Mycobacterium smegmatis ATCC 14468. Two of the compounds, 5-S-octyl-5-thio-alpha-D-arabinofuranoside (8) and 5-S-octyl-5-thio-beta-D-arabinofuranoside (11), showed MICs of 256 and 512 mu g/mL, respectively. Attempts to directly evaluate acyltransferase inhibitory activity of the arabinofuranosides against ag85C are also described. In conclusion, a new class of antimycobacterial arabinofuranosides has been discovered. Published by Elsevier Ltd.