2-hydroxy-3-(((1-hydroxy-2-methylpropan-2-yl)amino)methyl)naphthalene-1,4-dione | 118694-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-(((1-hydroxy-2-methylpropan-2-yl)amino)methyl)naphthalene-1,4-dione
• CAS: 118694-52-3
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: FLQBNESJVGPXKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.63
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-羟基-1,4-萘醌 、 2-氨基-2-甲基-1-丙醇 以 乙醇 、 水 为溶剂， 生成 2-hydroxy-3-(((1-hydroxy-2-methylpropan-2-yl)amino)methyl)naphthalene-1,4-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.03.039

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.