(Z)-3-(2-((1-(2-cyanophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-4-methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-3-(2-((1-(2-cyanophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-4-methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid
• 英文别名: (Z)-3-[2-[[1-(2-cyanophenyl)triazol-4-yl]methoxy]-4-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
• 化学式: C₂₅H₂₄N₄O₄
• 分子量: 444.49
• InChiKey: VVQYXHOJSRNNMY-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  蛇床子提取物 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 2.5h， 生成 (Z)-3-(2-((1-(2-cyanophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-4-methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid
  参考文献：
  名称：

  Click chemistry inspired synthesis and bioevaluation of novel triazolyl derivatives of osthol as potent cytotoxic agents

  摘要：

  A new series of diverse triazoles linked through the hydroxyl group of lactone ring opened osthol (1) were synthesized using click chemistry approach. All the derivatives were subjected to 3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazoliumbromide (MTT) cytotoxicity screening against a panel of seven different human cancer cell lines viz. colon (colo-205), colon (HCT-116), breast (T47D), lung (NCI-H322), lung (A549), prostate (PC-3) and Skin (A-431) to check their cytotoxic potential. Interestingly, among the tested molecules, most of the analogs displayed better cytotoxic activity than the parent osthol (1). Of the synthesized triazoles, compounds 8 showed the best activity with IC50 of 1.3, 4.9, 3.6, 41.0, 35.2, 26.4 and 7.2 μM against colon (Colo-205 and HCT-116), breast (T47D), lung (NCI-H322 and A549), prostate (PC-3) and Skin (A-431) cancer lines respectively. Compound 8 induced potent apoptotic effects in Colo-205 cells. The population of apoptotic cells increased from 11.4% in case of negative control to 24.1% at 25 μM of 8. Compound 8 also induced a remarkable decrease in mitochondrial membrane potential (ΛΨm) leading to apoptosis of cancer cells used. The present study resulted in identification of broad spectrum cytotoxic activity of analogs bearing electron withdrawing substituents, besides the enhanced selective activity of analogs with electron donating moieties.

  DOI：

  10.1016/j.ejmech.2014.07.069

文献信息

• Click chemistry inspired synthesis and bioevaluation of novel triazolyl derivatives of osthol as potent cytotoxic agents
  作者：Saleem Farooq、Shakeel-u-Rehman、Aashiq Hussain、Abid Hamid、Mushtaq A. Qurishi、Surrinder Koul

  DOI：10.1016/j.ejmech.2014.07.069

  日期：2014.9

  A new series of diverse triazoles linked through the hydroxyl group of lactone ring opened osthol (1) were synthesized using click chemistry approach. All the derivatives were subjected to 3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazoliumbromide (MTT) cytotoxicity screening against a panel of seven different human cancer cell lines viz. colon (colo-205), colon (HCT-116), breast (T47D), lung (NCI-H322), lung (A549), prostate (PC-3) and Skin (A-431) to check their cytotoxic potential. Interestingly, among the tested molecules, most of the analogs displayed better cytotoxic activity than the parent osthol (1). Of the synthesized triazoles, compounds 8 showed the best activity with IC50 of 1.3, 4.9, 3.6, 41.0, 35.2, 26.4 and 7.2 μM against colon (Colo-205 and HCT-116), breast (T47D), lung (NCI-H322 and A549), prostate (PC-3) and Skin (A-431) cancer lines respectively. Compound 8 induced potent apoptotic effects in Colo-205 cells. The population of apoptotic cells increased from 11.4% in case of negative control to 24.1% at 25 μM of 8. Compound 8 also induced a remarkable decrease in mitochondrial membrane potential (ΛΨm) leading to apoptosis of cancer cells used. The present study resulted in identification of broad spectrum cytotoxic activity of analogs bearing electron withdrawing substituents, besides the enhanced selective activity of analogs with electron donating moieties.