3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-methylbenzenesulfonate | 1376687-03-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-methylbenzenesulfonate
• 英文别名: [3-(3-Methylbut-2-enyl)-1,4-dioxonaphthalen-2-yl] 4-methylbenzenesulfonate
• CAS: 1376687-03-4
• 化学式: C₂₂H₂₀O₅S
• 分子量: 396.464
• InChiKey: BEGPCZRXAITNKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 在 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase

  摘要：

  Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 +/- 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.018

文献信息

• On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions
  作者：Eufrânio N. da Silva、Isadora M.M. de Melo、Emilay B.T. Diogo、Verenice A. Costa、José D. de Souza Filho、Wagner O. Valença、Celso A. Camara、Ronaldo N. de Oliveira、Alexandre S. de Araujo、Flávio S. Emery、Marcelo R. dos Santos、Carlos A. de Simone、Rubem F.S. Menna-Barreto、Solange L. de Castro

  DOI：10.1016/j.ejmech.2012.03.039

  日期：2012.6

  Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-beta-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, continuing our screening program for new trypanocidal compounds. Among all the substances, 16-18, 23, 25-29 and 30-33 were herein described for the first time and fifteen substances were identified as more potent than the standard drug benznidazole, with IC50/24 h values in the range of 10.9-101.5 mu M. Compounds 14 and 19 with Selectivity Index of 18.9 and 6.1 are important structures for further studies. (C) 2012 Elsevier Masson SAS. All rights reserved.