3-bromo-2,2-dimethyl-4-(4-phenyl-1,2,3-triazol-1-yl)-3,4-dihydro-2H-benzo[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: 3-bromo-2,2-dimethyl-4-(4-phenyl-1,2,3-triazol-1-yl)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
• 英文别名: (3R,4S)-3-bromo-2,2-dimethyl-4-(4-phenyltriazol-1-yl)-3,4-dihydrobenzo[h]chromene-5,6-dione
• 化学式: C₂₃H₁₈BrN₃O₃
• 分子量: 464.318
• InChiKey: JSNJUKIDLLBRQT-PGRDOPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 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：

  异烟肼 、 3-bromo-2,2-dimethyl-4-(4-phenyl-1,2,3-triazol-1-yl)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 在 溶剂黄146 作用下， 以40%的产率得到(Z)-N'-3-bromo-2,2-dimethyl-5-oxo-4-((4-phenyl-1H-1,2,3-triazol-1-yl)-3,4-dihydro-2H-benzo[h]chromen-6(5H)-ylidene)isonicotinohydrazide
  参考文献：
  名称：

  杂合分子作为抗分枝杆菌化合物的设计：异烟肼-萘醌衍生物的合成及其对结核分枝杆菌敏感和耐药菌株的活性。

  摘要：

  合成异烟肼-萘醌杂种并针对结核分枝杆菌的易感性菌株（H 37 Rv）和两个耐异烟肼菌株（INH R1和INH R2）进行评估。根据刃天青微量滴定法及其在粘附的小鼠单核巨噬细胞J774.A1细胞（ATCC TIB-67）中的细胞毒性，确定了衍生物的抗分枝杆菌活性。在针对三种结核分枝杆菌的评估的22种化合物中，有21种对H 37 Rv和INH R1（katG S315T）或INH R2（inhA C（-5）T）菌株具有一定的活性。化合物1a，2a和8a对INH R1菌株有效，化合物1a，1b，2a，3a，5a，5b和8a对INH R2菌株有效，MIC范围为3.12–6.25 µg / mL。化合物1b和5b对H 37 Rv的活性最高，MIC为0.78 µg / mL。基于选择性指数1b和5b可以被认为是安全的候选药物化合物。这些结果表明，喹诺酮类化合物可用作开发新的抗结核病药物和对结核分枝杆菌

  DOI：

  10.1016/j.bmc.2019.07.045
• 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 3-bromo-2,2-dimethyl-4-(4-phenyl-1,2,3-triazol-1-yl)-3,4-dihydro-2H-benzo[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.