2,2-dimethyl-3-((4-p-tolyl)-[1,2,3]triazol-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione | 1376687-02-3

• 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-3-((4-p-tolyl)-[1,2,3]triazol-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• 英文别名: 2,2-dimethyl-3-(4-p-tolyl-1H-1,2,3-triazol-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione；2,2-dimethyl-3-[4-(4-methylphenyl)triazol-1-yl]-3H-benzo[g][1]benzofuran-4,5-dione
• CAS: 1376687-02-3
• 化学式: C₂₃H₁₉N₃O₃
• 分子量: 385.422
• InChiKey: JABCUOWDFQATJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-((4-p-tolyl)-[1,2,3]triazol-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione 、 邻苯二胺 在 sodium acetate 、 溶剂黄146 作用下， 以72%的产率得到2,2-dimethyl-1-(4-(p-tolyl)-1H-1,2,3-triazol-1-yl)-1,2-dihydrobenzo[a]furo[2,3-c]phenazine
  参考文献：
  名称：

  On the Search for Potential Antimycobacterial Drugs: Synthesis of Naphthoquinoidal, Phenazinic and 1,2,3-Triazolic Compounds and Evaluation AgainstMycobacterium tuberculosis

  摘要：

  Fifteen naphthoquinones, sixteen phenazines and fifteen aryl triazoles were synthesized and evaluated against Mycobacterium tuberculosis. Twenty five substances are reported here for the first time and, among all of the compounds evaluated, six presented MIC (minimal inhibitory concentration) values <= 6.25 mu g mL(-1). These substances are promising antimycobacterial prototypes.

  DOI：

  10.5935/0103-5053.20150067
• 作为产物：
  描述：

  黄钟花醌 在 copper(ll) sulfate pentahydrate 、 双氧水 、 溴 、 sodium carbonate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 2,2-dimethyl-3-((4-p-tolyl)-[1,2,3]triazol-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  On the Search for Potential Antimycobacterial Drugs: Synthesis of Naphthoquinoidal, Phenazinic and 1,2,3-Triazolic Compounds and Evaluation AgainstMycobacterium tuberculosis

  摘要：

  Fifteen naphthoquinones, sixteen phenazines and fifteen aryl triazoles were synthesized and evaluated against Mycobacterium tuberculosis. Twenty five substances are reported here for the first time and, among all of the compounds evaluated, six presented MIC (minimal inhibitory concentration) values <= 6.25 mu g mL(-1). These substances are promising antimycobacterial prototypes.

  DOI：

  10.5935/0103-5053.20150067

文献信息

• Design, synthesis, and biological evaluation of 3-(1-benzotriazole)-nor-β-lapachones as NQO1-directed antitumor agents
  作者：Li-Qiang Wu、Xin Ma、Zhao-Peng Liu

  DOI：10.1016/j.bioorg.2021.104995

  日期：2021.8

  A series of novel 3-(1-benzotriazole)-nor-β-lapachones 5a–5l were synthesized as the NQO1-targeted anticancer agents. Most of these compounds displayed good antiproliferative activity against the breast cancer MCF-7, lung cancer A549 and hepatocellular carcinoma HepG2 cells in agreements with their NQO1 activity. Among them, compound 5k was identified as a favorable NQO1 substrate. It could activate

  合成了一系列新型 3-（1-苯并三唑）-nor-β-lapachones 5a - 5l作为 NQO1 靶向抗癌剂。大多数这些化合物对乳腺癌 MCF-7、肺癌 A549 和肝细胞癌 HepG2 细胞显示出良好的抗增殖活性，与其 NQO1 活性一致。其中，化合物5k被鉴定为有利的NQO1底物。它可以以NQO1依赖的方式激活ROS的产生，将肿瘤细胞周期阻滞在G0/G1期，促进肿瘤细胞凋亡，降低线粒体膜电位。在 HepG2 异种移植模型中，5k显着抑制肿瘤生长，而对动物体重没有影响。因此，5k 可能是进一步开发抗癌药物的良好线索。
• 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.
• On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions
  作者：Eufrânio N. da Silva、Isadora M.M. de Melo、Emilay B.T. Diogo、Verenice A. Costa、José D. de Souza Filho、Wagner O. Valença、Celso A. Camara、Ronaldo N. de Oliveira、Alexandre S. de Araujo、Flávio S. Emery、Marcelo R. dos Santos、Carlos A. de Simone、Rubem F.S. Menna-Barreto、Solange L. de Castro

  DOI：10.1016/j.ejmech.2012.03.039

  日期：2012.6

  Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-beta-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, continuing our screening program for new trypanocidal compounds. Among all the substances, 16-18, 23, 25-29 and 30-33 were herein described for the first time and fifteen substances were identified as more potent than the standard drug benznidazole, with IC50/24 h values in the range of 10.9-101.5 mu M. Compounds 14 and 19 with Selectivity Index of 18.9 and 6.1 are important structures for further studies. (C) 2012 Elsevier Masson SAS. All rights reserved.
• On the Search for Potential Antimycobacterial Drugs: Synthesis of Naphthoquinoidal, Phenazinic and 1,2,3-Triazolic Compounds and Evaluation Against<i>Mycobacterium tuberculosis</i>
  作者：Guilherme A. M. Jardim、Eduardo H. G. Cruz、Wagner O. Valença、Jarbas M. Resende、Bernardo L. Rodrigues、Daniela F. Ramos、Ronaldo N. Oliveira、Pedro E. A. Silva、Eufrânio N. da Silva Júnior

  DOI：10.5935/0103-5053.20150067

  日期：——

  Fifteen naphthoquinones, sixteen phenazines and fifteen aryl triazoles were synthesized and evaluated against Mycobacterium tuberculosis. Twenty five substances are reported here for the first time and, among all of the compounds evaluated, six presented MIC (minimal inhibitory concentration) values <= 6.25 mu g mL(-1). These substances are promising antimycobacterial prototypes.