2,2-dimethyl-1-(4-phenyl-1H-1,2,3-triazol-1-yl)-1,2-dihydrobenzo[a]furo[2,3-c]phenazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,2-dimethyl-1-(4-phenyl-1H-1,2,3-triazol-1-yl)-1,2-dihydrobenzo[a]furo[2,3-c]phenazine
• 英文别名: 4,4-Dimethyl-3-(4-phenyltriazol-1-yl)-5-oxa-14,21-diazapentacyclo[11.8.0.02,6.07,12.015,20]henicosa-1(21),2(6),7,9,11,13,15,17,19-nonaene；4,4-dimethyl-3-(4-phenyltriazol-1-yl)-5-oxa-14,21-diazapentacyclo[11.8.0.02,6.07,12.015,20]henicosa-1(21),2(6),7,9,11,13,15,17,19-nonaene
• 化学式: C₂₈H₂₁N₅O
• 分子量: 443.508
• InChiKey: WBTLXJMRDVPJHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  黄钟花醌 在 copper(ll) sulfate pentahydrate 、 双氧水 、 溴 、 sodium acetate 、 sodium carbonate 、 溶剂黄146 、 sodium ascorbate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 2,2-dimethyl-1-(4-phenyl-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

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.
• 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.