2-(phenylamino)-4H-spiro[naphthlene-1,2'-oxirane]-4-one | 57182-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(phenylamino)-4H-spiro[naphthlene-1,2'-oxirane]-4-one
• 英文别名: 3-Anilinospiro[naphthalene-4,2'-oxirane]-1-one
• CAS: 57182-40-8
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: ILGXBBBGJPMUHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 2-苯胺基-1,4-萘醌 以 乙醚 、 乙醇 为溶剂， 以69%的产率得到2-(phenylamino)-4H-spiro[naphthlene-1,2'-oxirane]-4-one
  参考文献：
  名称：

  Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives

  摘要：

  A series of eighteen quinones and structurally-related oxiranes were synthesized and evaluated for in vitro inhibitory activity against the chloroquine-sensitive 3D7 clone of the human malaria parasite Plasmodium falciparum. 2-amino and 2-allyloxynaphthoquinones exhibited important antiplasmodial activity (median inhibitory concentrations (IC50) < 10 mu M). Oxiranes 6 and 25, prepared respectively by reaction of alpha-lapachone and tetrachloro-p-quinone with diazomethane in a mixture of ether and ethanol, exhibited the highest antiplasmodial activity and low cytotoxicity against human fibroblasts (MCR-5 cell line). The active compounds could represent a good prototype for an antimalarial lead molecule. (C) 2015 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.11.020

文献信息

• Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives
  作者：Paula F. Carneiro、Maria C.R.F. Pinto、Roberta K.F. Marra、Fernando de C. da Silva、Jackson A.L.C. Resende、Luiz F. Rocha e Silva、Hilkem G. Alves、Gleyce S. Barbosa、Marne C. de Vasconcellos、Emerson S. Lima、Adrian M. Pohlit、Vitor F. Ferreira

  DOI：10.1016/j.ejmech.2015.11.020

  日期：2016.1

  A series of eighteen quinones and structurally-related oxiranes were synthesized and evaluated for in vitro inhibitory activity against the chloroquine-sensitive 3D7 clone of the human malaria parasite Plasmodium falciparum. 2-amino and 2-allyloxynaphthoquinones exhibited important antiplasmodial activity (median inhibitory concentrations (IC50) < 10 mu M). Oxiranes 6 and 25, prepared respectively by reaction of alpha-lapachone and tetrachloro-p-quinone with diazomethane in a mixture of ether and ethanol, exhibited the highest antiplasmodial activity and low cytotoxicity against human fibroblasts (MCR-5 cell line). The active compounds could represent a good prototype for an antimalarial lead molecule. (C) 2015 Published by Elsevier Masson SAS.