3-isobutyl-3-(3-isobutyl-1,4-dioxo-1,4-dihydronaphthalen-2-yloxy)naphthalene-1,2,4(3H)-trione | 1266606-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-isobutyl-3-(3-isobutyl-1,4-dioxo-1,4-dihydronaphthalen-2-yloxy)naphthalene-1,2,4(3H)-trione
• 英文别名: 3-isobutyl-3-(3-isobutyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yloxy)-naphthalene-1,2,4-trione；3-(2-Methylpropyl)-3-[3-(2-methylpropyl)-1,4-dioxonaphthalen-2-yl]oxynaphthalene-1,2,4-trione
• CAS: 1266606-68-1
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: QYDYSRCPCQQVAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-isobutyl-3-(3-isobutyl-1,4-dioxo-1,4-dihydronaphthalen-2-yloxy)naphthalene-1,2,4(3H)-trione 、 邻苯二胺 在 sodium acetate 、 溶剂黄146 作用下， 以40%的产率得到2-isobutyl-3-(6-isobutyl-5-oxo-5,6-dihydrobenzo[a]phenazin-6-yloxy)naphthalene-1,4-dione
  参考文献：
  名称：

  Quinonoid and phenazine compounds: Synthesis and evaluation against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis

  摘要：

  Several quinonoid and phenazine compounds were synthesized in moderate to high yields and showed activity against H(37)Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The cytotoxity of the compounds were evaluated against human peripheral blood mononuclear cells (PBMC) and these substances emerge as promising antitubercular prototypes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.026
• 作为产物：
  描述：

  4-hydroxy-3-(2-methylpropyl)naphthalene-1,2-dione 在 lead dioxide 、 溶剂黄146 作用下， 反应 0.03h， 以70%的产率得到3-isobutyl-3-(3-isobutyl-1,4-dioxo-1,4-dihydronaphthalen-2-yloxy)naphthalene-1,2,4(3H)-trione
  参考文献：
  名称：

  Synthesis and evaluation of quinonoid compounds against tumor cell lines

  摘要：

  Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 mu M for some compounds. The beta-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.006

文献信息

• Quinonoid and phenazine compounds: Synthesis and evaluation against H37Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis
  作者：Paula F. Carneiro、Maria do Carmo F.R. Pinto、Tatiane S. Coelho、Bruno C. Cavalcanti、Cláudia Pessoa、Carlos A. de Simone、Isabelle K.C. Nunes、Nathalia M. de Oliveira、Renata G. de Almeida、Antonio V. Pinto、Kelly C.G. de Moura、Pedro A. da Silva、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2011.07.026

  日期：2011.9

  Several quinonoid and phenazine compounds were synthesized in moderate to high yields and showed activity against H(37)Rv, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The cytotoxity of the compounds were evaluated against human peripheral blood mononuclear cells (PBMC) and these substances emerge as promising antitubercular prototypes. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and evaluation of quinonoid compounds against tumor cell lines
  作者：Eufrânio N. da Silva、Bruno C. Cavalcanti、Tiago T. Guimarães、Maria do Carmo F.R. Pinto、Igor O. Cabral、Cláudia Pessoa、Letícia V. Costa-Lotufo、Manoel O. de Moraes、Carlos K.Z. de Andrade、Marcelo R. dos Santos、Carlos A. de Simone、Marilia O.F. Goulart、Antonio V. Pinto

  DOI：10.1016/j.ejmech.2010.11.006

  日期：2011.1

  Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 mu M for some compounds. The beta-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII). (C) 2010 Elsevier Masson SAS. All rights reserved.