2,2-dimethyl-2,3-dihydro-4H-spiro[naphtho[2,3-b]furan-9,2'-oxiran]-4-one | 1037059-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2,2-dimethyl-2,3-dihydro-4H-spiro[naphtho[2,3-b]furan-9,2'-oxiran]-4-one
• 英文别名: 2,2-dimethyl-2H-spiro[naphtho[2,3-b]furan-9,2'-oxirane]-4(3H)-one；2,2-dimethylspiro[3H-benzo[f][1]benzofuran-9,2'-oxirane]-4-one
• CAS: 1037059-31-6
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: OJRFSQGFMITKIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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 、 nor-α-lapachone 以 乙醚 、 乙醇 为溶剂， 反应 72.0h， 以60%的产率得到2,2-dimethyl-2,3-dihydro-4H-spiro[naphtho[2,3-b]furan-9,2'-oxiran]-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

• Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones
  作者：Eufrânio N. da Silva Júnior、Maria Cecília B.V. de Souza、Michelle C. Fernandes、Rubem F.S. Menna-Barreto、Maria do Carmo F.R. Pinto、Francisco de Assis Lopes、Carlos Alberto de Simone、Carlos Kleber Z. Andrade、Antônio V. Pinto、Vitor F. Ferreira、Solange L. de Castro

  DOI：10.1016/j.bmc.2008.03.032

  日期：2008.5

  New naphthoquinone derivatives were synthesized and assayed against bloodstream trypomastigote forms of Trypanosoma cruzi, the etiological agent of Chagas' disease. The compounds were rationalized based on hybrid drugs and appear as important compounds against this parasite. From nor-lapachol were prepared five substituted ortho-naphthofuranquinones, a non-substituted para-naphthofuranquinone, a new oxyrane and an azide and from alpha-lapachone a new non-substituted para-naphthofuranquinone. Other five substituted ortho-naphthofuranquinones recently designed as cytotoxic, were also evaluated. The most active compounds were the ortho naphthofuranquinones 3-(4-methoxyphenylamino)-2,3-dihydro-2,2-dimethylnaphtho[1,2-b]furan-4,5-dione and 3-(3-nitrophenylamino)-2,3-dihydro-2,2-dimethylnaphtho[1,2-b]furan-4,5-dione with trypanocidal activity higher than that of benznidazole, the standard drug. The compounds were rationalized based on hybrid drugs and appear as important compounds against T. cruzi. The trypanocidal activity of these substances endowed with redox properties representing a good starting point for a medicinal chemistry program aiming the chemotherapy of Chagas' disease. (c) 2008 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.
• 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.