3-(1,4-Dihydroxynaphthalen-2-ylsulfonyl)propanoic acid | 1101874-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1,4-Dihydroxynaphthalen-2-ylsulfonyl)propanoic acid
• 英文别名: 3-(1,4-dihydroxynaphthalen-2-yl)sulfonylpropanoic acid
• CAS: 1101874-40-1
• 化学式: C₁₃H₁₂O₆S
• 分子量: 296.301
• InChiKey: AEEJSZCMSYRVSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  monosodium salt of 3-sulfinopropanoic acid 、 1,4-萘醌 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 3-(1,4-Dihydroxynaphthalen-2-ylsulfonyl)propanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors

  摘要：

  A series of analogs of 2-tosylnaphthalene-1,4-diol were prepared and were found to be potent 10-20 nM reversible inhibitors of the Escherichia coli FabH enzyme. The inhibitors were also effective but to a lesser degree (30 nM-5 mu M), against the Mycobacterium tuberculosis and Plasmodium falciparum FabH enzymes. Preliminary SAR studies demonstrated that the sulfonyl group and naphthalene-1,4 diol were required for activity against all enzymes but the toluene portion could be significantly altered and leads to either modest increases or decreases in activity against the three enzymes. The in vitro activity of the analogs against E. coli FabH parallel the in vivo activity against E. coli TolC strain and many of the compounds were also shown to have antimalarial activity against P. falciparum. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.097

文献信息

• Synthesis and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors
  作者：Mamoun M. Alhamadsheh、Norman C. Waters、Sarbjot Sachdeva、Patricia Lee、Kevin A. Reynolds

  DOI：10.1016/j.bmcl.2008.10.097

  日期：2008.12

  A series of analogs of 2-tosylnaphthalene-1,4-diol were prepared and were found to be potent 10-20 nM reversible inhibitors of the Escherichia coli FabH enzyme. The inhibitors were also effective but to a lesser degree (30 nM-5 mu M), against the Mycobacterium tuberculosis and Plasmodium falciparum FabH enzymes. Preliminary SAR studies demonstrated that the sulfonyl group and naphthalene-1,4 diol were required for activity against all enzymes but the toluene portion could be significantly altered and leads to either modest increases or decreases in activity against the three enzymes. The in vitro activity of the analogs against E. coli FabH parallel the in vivo activity against E. coli TolC strain and many of the compounds were also shown to have antimalarial activity against P. falciparum. (C) 2008 Published by Elsevier Ltd.