(3R,4S)-3-bromo-4-[4-(4-methoxyphenyl)triazol-1-yl]-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione

• 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: (3R,4S)-3-bromo-4-[4-(4-methoxyphenyl)triazol-1-yl]-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
• 化学式: C₂₄H₂₀BrN₃O₄
• 分子量: 494.344
• InChiKey: WMMRPQPHXVNHGI-WMZHIEFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  邻苯二胺 、 (3R,4S)-3-bromo-4-[4-(4-methoxyphenyl)triazol-1-yl]-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione 在 sodium acetate 、 溶剂黄146 作用下， 以82%的产率得到2-bromo-1-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-3,3-dimethyl-2,3-dihydro-1H-benzo[a]pyrano[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：

  3,4-二氢-2,2-二甲基-2H-萘并[1,2-B]吡喃-5,6-二酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 生成 (3R,4S)-3-bromo-4-[4-(4-methoxyphenyl)triazol-1-yl]-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-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

• The evaluation of quinonoid compounds against Trypanosoma cruzi: Synthesis of imidazolic anthraquinones, nor-β-lapachone derivatives and β-lapachone-based 1,2,3-triazoles
  作者：Eufrânio N. da Silva Júnior、Tiago T. Guimarães、Rubem F.S. Menna-Barreto、Maria do Carmo F.R. Pinto、Carlos A. de Simone、Claudia Pessoa、Bruno C. Cavalcanti、José R. Sabino、Carlos Kleber Z. Andrade、Marilia O.F. Goulart、Solange L. de Castro、Antônio V. Pinto

  DOI：10.1016/j.bmc.2010.03.029

  日期：2010.5

  In continuing our screening program of naphthoquinone activity against Trypanosoma cruzi, the aetiological agent of Chagas' disease, new beta-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-beta-lapachones, 3-alkoxy-nor-beta-lapachones and imidazole anthraquinones were synthesised and evaluated against bloodstream trypomastigote forms of the parasite. Compounds 2,2-dimethyl-3-(2,4-dibromophenylamino)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione, IC50/24 h 24.9 +/- 7.4 and 4-azido-3-bromo-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione with 23.4 +/- 3.8 mu M showed a trypanosomicidal activity higher than benznidazole. These results demonstrate the potential of naphthoquinone derivatives as novel structures for the development of alternative drugs for Chagas' disease. (c) 2010 Elsevier Ltd. 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.
• 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.