8-(acetoxymethyl)-1-naphthyl methyl disulfide | 118715-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-(acetoxymethyl)-1-naphthyl methyl disulfide
• 英文别名: 1-Naphthalenemethanol, 8-(methyldithio)-, acetate；[8-(methyldisulfanyl)naphthalen-1-yl]methyl acetate
• CAS: 118715-01-8
• 化学式: C₁₄H₁₄O₂S₂
• 分子量: 278.396
• InChiKey: PRXJKNLUFIJNDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±27.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(acetoxymethyl)-1-naphthyl methyl disulfide 在 三乙胺 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到2H-naphtho<1,8-b,c>thiophene
  参考文献：
  名称：

  A novel prodrug of an impermeant inhibitor of 3-deoxy-D-manno-2-octulosonate cytidylyltransferase has antibacterial activity

  摘要：

  Although 8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonic acid (2) is a potent inhibitor of 3-deoxy-D-manno-octulosonate cytidylyltransferase (CMP-KDO synthetase), it is unable to reach its cytoplasmic target and is therefore inactive as an antibacterial agent. However, esterification of 2 with 8-(hydroxymethyl)-1-naphthyl methyl disulfide (8) generates a prodrug (12), which gains entry into bacterial cells. Intracellular reduction of the disulfide leads to a rapid, intramolecular, displacement of the acid 2, which then inhibits the growth of Gram-negative bacteria by interfering with the biosynthesis of lipopolysaccharide.

  DOI：

  10.1021/jm00123a021
• 作为产物：
  描述：

  8-氯萘-1-硫醇 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 8-(acetoxymethyl)-1-naphthyl methyl disulfide
  参考文献：
  名称：

  A novel prodrug of an impermeant inhibitor of 3-deoxy-D-manno-2-octulosonate cytidylyltransferase has antibacterial activity

  摘要：

  Although 8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonic acid (2) is a potent inhibitor of 3-deoxy-D-manno-octulosonate cytidylyltransferase (CMP-KDO synthetase), it is unable to reach its cytoplasmic target and is therefore inactive as an antibacterial agent. However, esterification of 2 with 8-(hydroxymethyl)-1-naphthyl methyl disulfide (8) generates a prodrug (12), which gains entry into bacterial cells. Intracellular reduction of the disulfide leads to a rapid, intramolecular, displacement of the acid 2, which then inhibits the growth of Gram-negative bacteria by interfering with the biosynthesis of lipopolysaccharide.

  DOI：

  10.1021/jm00123a021

文献信息

• NORBECK, DANIEL W.;ROSENBROOK, WILLIAM;KRAMER, JAMES B.;GRAMPOVNIK, DAVID+, J. MED. CHEM., 32,(1989) N, C. 625-629
  作者：NORBECK, DANIEL W.、ROSENBROOK, WILLIAM、KRAMER, JAMES B.、GRAMPOVNIK, DAVID+

  DOI：——

  日期：——
• A novel prodrug of an impermeant inhibitor of 3-deoxy-D-manno-2-octulosonate cytidylyltransferase has antibacterial activity
  作者：Daniel W. Norbeck、William Rosenbrook、James B. Kramer、David J. Grampovnik、Paul A. Lartey

  DOI：10.1021/jm00123a021

  日期：1989.3

  Although 8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonic acid (2) is a potent inhibitor of 3-deoxy-D-manno-octulosonate cytidylyltransferase (CMP-KDO synthetase), it is unable to reach its cytoplasmic target and is therefore inactive as an antibacterial agent. However, esterification of 2 with 8-(hydroxymethyl)-1-naphthyl methyl disulfide (8) generates a prodrug (12), which gains entry into bacterial cells. Intracellular reduction of the disulfide leads to a rapid, intramolecular, displacement of the acid 2, which then inhibits the growth of Gram-negative bacteria by interfering with the biosynthesis of lipopolysaccharide.