1,3-dimethyl-7-[2-({1-[3-(4,5,6,7-tetrabromo-1H-1,3-benzodiazol-1-yl)propyl]-1H-1,2,3-triazol-4-yl}methoxy)propyl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1,3-dimethyl-7-[2-({1-[3-(4,5,6,7-tetrabromo-1H-1,3-benzodiazol-1-yl)propyl]-1H-1,2,3-triazol-4-yl}methoxy)propyl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• 英文别名: 1,3-Dimethyl-7-[2-[[1-[3-(4,5,6,7-tetrabromobenzimidazol-1-yl)propyl]triazol-4-yl]methoxy]propyl]purine-2,6-dione；1,3-dimethyl-7-[2-[[1-[3-(4,5,6,7-tetrabromobenzimidazol-1-yl)propyl]triazol-4-yl]methoxy]propyl]purine-2,6-dione
• 化学式: C₂₃H₂₃Br₄N₉O₃
• 分子量: 793.11
• InChiKey: MCGQNKFILJYHSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  羟丙茶碱 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 溶剂黄146 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 、 叔丁醇 为溶剂， 反应 3.17h， 生成 1,3-dimethyl-7-[2-({1-[3-(4,5,6,7-tetrabromo-1H-1,3-benzodiazol-1-yl)propyl]-1H-1,2,3-triazol-4-yl}methoxy)propyl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione
  参考文献：
  名称：

  Synthesis of novel proxyphylline derivatives with dual Anti-Candida albicans and anticancer activity

  摘要：

  Three out of 16 newly synthesized 1,3-dimethylxanthine derivatives (proxyphylline analogues) exhibited consistencies between antifungal and anticancer properties. Proxyphylline possessing 1-(10H-phenothiazin-10-yl)propan-2-yl (6) and polybrominated benzimidazole (41) or benzotriazole moiety (42) remained selectively cidal against Candida albicans (lg R >= 3 at conc. of 31, 36 and 20 mu M, respectively) however not against normal mammalian Vero cell line in vitro (IC50 >= 280 mu M) and Galleria mellonella in vivo. These compounds also displayed moderate antineoplastic activity against human breast adenocarcinoma (MCF-7) cell line (EC50 = 80 mu M) and high against peripheral blood T lymphoblast (CCRF-CEM) (EC50 = 6.3-6.5 mu M). In addition, 6 and 42 exerted: (1) dual activity against fungal adhesion and damage mature biofilm; (2) necrosis of planktonic cells due to loss of membrane function and of structural integrity; (3) biochemical (inhibition of sessile cell respiration) and morphological changes in cell wall polysaccharide contents. Therefore, leading proxyphylline derivatives can be employed to prevent cancer-associated biofilm Candida infections. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.077