2-(3-(2-oxo-2-p-tolylethylthio)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)isoindoline-1,3-dione | 1394017-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-(2-oxo-2-p-tolylethylthio)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)isoindoline-1,3-dione
• 英文别名: 2-[3-[2-(4-Methylphenyl)-2-oxoethyl]sulfanyl-5-(3,4,5-trimethoxyphenyl)-1,2,4-triazol-4-yl]isoindole-1,3-dione
• CAS: 1394017-46-9
• 化学式: C₂₈H₂₄N₄O₆S
• 分子量: 544.588
• InChiKey: YYNXKYWUDISDHM-UHFFFAOYSA-N

物化性质

• 沸点：
  782.0±70.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-amino-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol 在 三乙胺 、 zinc dibromide 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 2-(3-(2-oxo-2-p-tolylethylthio)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  One-pot synthesis of novel isoindoline-1,3-dione derivatives bearing 1,2,4-triazole moiety and their preliminary biological evaluation

  摘要：

  A series of novel isoindoline-1,3-diones containing 1,2,4-triazole moiety were synthesized via a one-pot reaction. Bioassay indicated that compounds 33, 35, 37 and 39 exhibited much higher activities against Botryodiplodia theobromae than commercial fungicide triadimefon at the dosage of 150 mg/L. Most interestingly, compounds 36,37 and 45 displayed much stronger antitumor activities against four human cell lines than positive control Fluorouracil. Particularly, compound 37 had four-fold improvement compared to Fluorouracil in inhibiting A549 and HepG2 cell proliferation with IC50 values of 6.76 and 9.44 mu M, respectively. Further flow-activated cell sorting analysis revealed that compound 37 displayed apoptosis-inducing effect on HepG2 cells in a dose-dependent manner. These encouraging results could be helpful for the development of new antitumor compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.041

文献信息

• One-pot synthesis of novel isoindoline-1,3-dione derivatives bearing 1,2,4-triazole moiety and their preliminary biological evaluation
  作者：Pei-Liang Zhao、Wei-Feng Ma、An-Na Duan、Min Zou、Yi-Chen Yan、Wen-Wei You、Shu-Guang Wu

  DOI：10.1016/j.ejmech.2012.06.041

  日期：2012.8

  A series of novel isoindoline-1,3-diones containing 1,2,4-triazole moiety were synthesized via a one-pot reaction. Bioassay indicated that compounds 33, 35, 37 and 39 exhibited much higher activities against Botryodiplodia theobromae than commercial fungicide triadimefon at the dosage of 150 mg/L. Most interestingly, compounds 36,37 and 45 displayed much stronger antitumor activities against four human cell lines than positive control Fluorouracil. Particularly, compound 37 had four-fold improvement compared to Fluorouracil in inhibiting A549 and HepG2 cell proliferation with IC50 values of 6.76 and 9.44 mu M, respectively. Further flow-activated cell sorting analysis revealed that compound 37 displayed apoptosis-inducing effect on HepG2 cells in a dose-dependent manner. These encouraging results could be helpful for the development of new antitumor compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.