2-(allyloxy)-4H-spiro[naphthalene-1,2'-oxirane]-4-one | 1393135-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(allyloxy)-4H-spiro[naphthalene-1,2'-oxirane]-4-one
• 英文别名: 3-Prop-2-enoxyspiro[naphthalene-4,2'-oxirane]-1-one
• CAS: 1393135-61-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: RTCKVRNMXULGCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 2-allyloxy-1,4-naphthoquinone 以 乙醚 、 乙醇 为溶剂， 反应 96.0h， 以35%的产率得到2-(allyloxy)-4H-spiro[naphthalene-1,2'-oxirane]-4-one
  参考文献：
  名称：

  New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms

  摘要：

  New oxirane derivatives were synthesized using six naphthoquinones as the starting materials. Our biological results showed that these oxiranes acted as trypanocidal agents against Trypanosoma cruzi with minimal cytotoxicity in the VERO cell line compared to naphthoquinones. In particular, oxirane derivative 14 showed low cytotoxicity in a mammalian cell line and exhibited better activity against epimastigote forms of T. cruzi than the current drug used to treat Chagas disease, benznidazole. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.027

文献信息

• New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms
  作者：Paula F. Carneiro、Samara B. do Nascimento、Antonio V. Pinto、Maria do Carmo F.R. Pinto、Guilherme C. Lechuga、Dilvani O. Santos、Helvécio M. dos Santos Júnior、Jackson A.L.C. Resende、Saulo C. Bourguignon、Vitor F. Ferreira

  DOI：10.1016/j.bmc.2012.06.027

  日期：2012.8

  New oxirane derivatives were synthesized using six naphthoquinones as the starting materials. Our biological results showed that these oxiranes acted as trypanocidal agents against Trypanosoma cruzi with minimal cytotoxicity in the VERO cell line compared to naphthoquinones. In particular, oxirane derivative 14 showed low cytotoxicity in a mammalian cell line and exhibited better activity against epimastigote forms of T. cruzi than the current drug used to treat Chagas disease, benznidazole. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.