4-(4-(2-hydroxybutan-2-yl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione | 1443219-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 4-(4-(2-hydroxybutan-2-yl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
• 英文别名: 4-[4-(2-Hydroxybutan-2-yl)triazol-1-yl]-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione；4-[4-(2-hydroxybutan-2-yl)triazol-1-yl]-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
• CAS: 1443219-28-0
• 化学式: C₂₁H₂₃N₃O₄
• 分子量: 381.431
• InChiKey: ZFNUJYXVCGAIRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ALPHA-拉杷醌 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 4-(4-(2-hydroxybutan-2-yl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
  参考文献：
  名称：

  Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: Synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide–alkyne cycloaddition

  摘要：

  Continuing our screening program for novel anti-parasite compounds, we synthesized seven 1,4-naphthoquinones coupled to 1,2,3-triazoles, five nor-beta-lapachone-based 1,2,3-triazoles and ten alpha-lapachone-based 1,2,3-triazoles. These and other naphthoquinonoid compounds were evaluated for their activity against promastigote forms of antimony-sensitive and -resistant strains of Leishmania infantum (syn. Leishmania chagasi) and Leishmania amazonensis. The toxicity of these compounds to mammalian cells was also examined. The substances were more potent than an antimonial drug, with IC50 values ranging from 1.0 to 50.7 mu M. Nor-alpha-lapachone derivatives showed the highest antileishmanial activity, with selectivity indices in the range of 10-15. These compounds emerged as important leads for further investigation as antileishmanial agents. Additionally, one of these compounds exhibited cross-resistance in Sb-resistant Leishmania and could provide a molecular tool for investigating the multidrug resistance mechanisms in Leishmania parasites. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.038

文献信息

• Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: Electrochemical studies on the effects of the quinoidal moiety
  作者：Emilay B.T. Diogo、Gleiston G. Dias、Bernardo L. Rodrigues、Tiago T. Guimarães、Wagner O. Valença、Celso A. Camara、Ronaldo N. de Oliveira、Mauro G. da Silva、Vitor F. Ferreira、Yen Galdino de Paiva、Marilia O.F. Goulart、Rubem F.S. Menna-Barreto、Solange L. de Castro、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.bmc.2013.08.055

  日期：2013.11

  In our continued search for novel trypanocidal compounds, twenty-six derivatives of para-and orthonaphthoquinones coupled to 1,2,3-triazoles were synthesized. These compounds were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease. Compounds 17-24, 28-30 and 36-38 are described herein for the first time. Three of these novel compounds (28-30) were found to be more potent than the standard drug benznidazole, with IC50/24 h values between 6.8 and 80.8 mu M. Analysis of the toxicity to heart muscle cells led to LC50/24 h of <125, 63.1 and 281.6 mu M for 28, 29 and 30, respectively. Displaying a selectivity index of 34.3, compound 30 will be further evaluated in vivo. The electrochemical properties of selected compounds were evaluated in an attempt to find correlations with trypanocidal activity, and it was observed that more electrophilic quinones were generally more potent. (C) 2013 Elsevier Ltd. All rights reserved.
• Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: Synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide–alkyne cycloaddition
  作者：Tiago T. Guimarães、Maria do Carmo F.R. Pinto、Juliane S. Lanza、Maria N. Melo、Rubens L. do Monte-Neto、Isadora M.M. de Melo、Emilay B.T. Diogo、Vitor F. Ferreira、Celso A. Camara、Wagner O. Valença、Ronaldo N. de Oliveira、Frédéric Frézard、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2013.02.038

  日期：2013.5

  Continuing our screening program for novel anti-parasite compounds, we synthesized seven 1,4-naphthoquinones coupled to 1,2,3-triazoles, five nor-beta-lapachone-based 1,2,3-triazoles and ten alpha-lapachone-based 1,2,3-triazoles. These and other naphthoquinonoid compounds were evaluated for their activity against promastigote forms of antimony-sensitive and -resistant strains of Leishmania infantum (syn. Leishmania chagasi) and Leishmania amazonensis. The toxicity of these compounds to mammalian cells was also examined. The substances were more potent than an antimonial drug, with IC50 values ranging from 1.0 to 50.7 mu M. Nor-alpha-lapachone derivatives showed the highest antileishmanial activity, with selectivity indices in the range of 10-15. These compounds emerged as important leads for further investigation as antileishmanial agents. Additionally, one of these compounds exhibited cross-resistance in Sb-resistant Leishmania and could provide a molecular tool for investigating the multidrug resistance mechanisms in Leishmania parasites. (C) 2013 Elsevier Masson SAS. All rights reserved.