8-氯萘-1-硫醇 | 61209-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 8-氯萘-1-硫醇
• 英文名称: 8-chloro-1-naphthalenethiol
• 英文别名: 8-chloro-naphthalene-1-thiol；8-Chlor-naphthalin-1-thiol；(8-Chlor-naphthyl-(1))-mercaptan；8-Chlor-thionaphthol-(1)；8-Chlor-1-naphthalinthiol；8-Chloronaphthalene-1-thiol
• CAS: 61209-66-3
• 化学式: C₁₀H₇ClS
• mdl: MFCD18975538
• 分子量: 194.685
• InChiKey: YICMQGKNGMHCIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  8-氯萘-1-硫醇 在 4-二甲氨基吡啶 、 三乙胺 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 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：

  氯苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 作用下， 生成 8-氯萘-1-硫醇
  参考文献：
  名称：

  Dikshit; Tilak, Proceedings - Indian Academy of Sciences, Section A, 1951, # 33, p. 78,82

  摘要：

  DOI：

文献信息

• DE455280
  申请人：——

  公开号：——

  公开（公告）日：——
• Rabindran; Tilak, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 564,569
  作者：Rabindran、Tilak

  DOI：——

  日期：——
• 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.
• Dikshit; Tilak, Proceedings - Indian Academy of Sciences, Section A, 1951, # 33, p. 78,82
  作者：Dikshit、Tilak

  DOI：——

  日期：——