2-(4-propylbenzenesulfonyl)naphthalene-1,4-diol | 1101874-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-propylbenzenesulfonyl)naphthalene-1,4-diol
• 英文别名: 2-(4-Propylphenylsulfonyl)naphthalene-1,4-diol；2-(4-propylphenyl)sulfonylnaphthalene-1,4-diol
• CAS: 1101874-42-3
• 化学式: C₁₉H₁₈O₄S
• 分子量: 342.416
• InChiKey: BCECDLBGKYFWCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-propyl-benzenesulfonyl)-[1,4]naphthoquinone 在 sodium tetrahydroborate 作用下， 反应 1.0h， 以89%的产率得到2-(4-propylbenzenesulfonyl)naphthalene-1,4-diol
  参考文献：
  名称：

  Synthesis of arylsulfonyl-quinones and arylsulfonyl-1,4-diols as FabH inhibitors: Pd-catalyzed direct C-sulfone formation by CS coupling of quinones with arylsulfonyl chloride

  摘要：

  The Pd-catalyzed direct C-sulfone formation by C-S coupling of quinones with arylsulfonyl chloride has been developed. This methodology provides an effective, convenient method for the synthesis of aryl-sulfonyl-quinones and arylsulfonyl-1,4-diols, which are potent inhibitors of FabH. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.023

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.
• Synthesis of arylsulfonyl-quinones and arylsulfonyl-1,4-diols as FabH inhibitors: Pd-catalyzed direct C-sulfone formation by CS coupling of quinones with arylsulfonyl chloride
  作者：Bingyang Ge、Dawei Wang、Weifu Dong、Piming Ma、Yongliang Li、Yuqiang Ding

  DOI：10.1016/j.tetlet.2014.08.023

  日期：2014.10

  The Pd-catalyzed direct C-sulfone formation by C-S coupling of quinones with arylsulfonyl chloride has been developed. This methodology provides an effective, convenient method for the synthesis of aryl-sulfonyl-quinones and arylsulfonyl-1,4-diols, which are potent inhibitors of FabH. (C) 2014 Elsevier Ltd. All rights reserved.