5-(4-(tert-butyldimethylsilyloxy)-3,5-dimethoxyphenyl)-3-(3,4,5-trimethoxy-phenyl)-4,5-dihydroisoxazole | 1246651-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-(tert-butyldimethylsilyloxy)-3,5-dimethoxyphenyl)-3-(3,4,5-trimethoxy-phenyl)-4,5-dihydroisoxazole
• 英文别名: Tert-butyl-[2,6-dimethoxy-4-[3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]phenoxy]-dimethylsilane
• CAS: 1246651-07-9
• 化学式: C₂₆H₃₇NO₇Si
• 分子量: 503.668
• InChiKey: WIXFECLLGLYLPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(4-(tert-butyldimethylsilyloxy)-3,5-dimethoxyphenyl)-3-(3,4,5-trimethoxy-phenyl)-4,5-dihydroisoxazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到2,6-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)phenol
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents

  摘要：

  A series of 3,5-diaryl-isoxazoline/isoxazole linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates were prepared. These conjugates showed potent anticancer activity with GI(50) values in the range of <0.1-3.6 mu M. Some of these PBD conjugates (6a-c) with promising anticancer activity were further investigated on the cell cycle distribution. Moreover, these PBD conjugates exhibited G0/G1 arrest, enhancement in the levels of p53 protein as well as mitochondrial-mediated intrinsic pathway, leading to release of cytochrome c, activation of caspase-3, cleavage of PARP and subsequent apoptotic cell death. Hence these PBD conjugates with 6a being the most potent one could be be taken up for preclinical studies either alone or in combination with existing therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.047
• 作为产物：
  描述：

  (1,1-dimethylethyl)(4-ethenyl-2,6-dimethoxyphenoxy)dimethylsilane 、 3,4,5-三甲氧基苯甲醛肟 在 sodium hypochlorite 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 以60%的产率得到5-(4-(tert-butyldimethylsilyloxy)-3,5-dimethoxyphenyl)-3-(3,4,5-trimethoxy-phenyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents

  摘要：

  A series of 3,5-diaryl-isoxazoline/isoxazole linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates were prepared. These conjugates showed potent anticancer activity with GI(50) values in the range of <0.1-3.6 mu M. Some of these PBD conjugates (6a-c) with promising anticancer activity were further investigated on the cell cycle distribution. Moreover, these PBD conjugates exhibited G0/G1 arrest, enhancement in the levels of p53 protein as well as mitochondrial-mediated intrinsic pathway, leading to release of cytochrome c, activation of caspase-3, cleavage of PARP and subsequent apoptotic cell death. Hence these PBD conjugates with 6a being the most potent one could be be taken up for preclinical studies either alone or in combination with existing therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.047