(E)-3-(4-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one | 775531-32-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(4-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 775531-32-3
• 化学式: C₁₆H₁₅NO₂
• mdl: MFCD01974976
• 分子量: 253.301
• InChiKey: TZCMYPASAIZADP-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 硫酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 1.17h， 以46%的产率得到(E)-3-(4-azidophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of 5,6-diaryl-1,2,4-triazines hybrids as potential apoptosis inducers

  摘要：

  A series of 5,6-diaryl-1,2,4-triazines hybrids bearing a 1,2,3-triazole linker were synthesized by molecular hybridization strategy and evaluated for antiproliferative activity against three selected cancer cell lines (MGC-803, EC-109 and PC-3). The first structure-activity relationship (SAR) for these 5,6-diaryl-1,2,4-triazines is explored in this report with evaluation of 15 variants of the structural class. Among these chemical derivatives, 3-(((1-(4-fluorobenzy1)-1H-1,2,3-triazol-4-yl)methyl)thio)-5,6-dipheny1-1,2,4-triazine(11E) showed the more potent inhibitory effect against three cell lines than 5-Fu. Cellular mechanism studies in MGC-803 cells elucidated 11E inhibited colony formation and arrested cell cycle at G2/M phase. Furthermore, compound 11E caused morphological changes, decreased mitochondrial membrane potential, and induced apoptosis through the apoptosis-related proteins in MGC-803 cells. It was the first time, to our knowledge, that 5,6-diaryl-1,2,4-triazines bearing a 1,2,3-triazole linker were used as potential apoptosis inducers. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.07.011
• 作为产物：
  描述：

  (E)-3-(4-azidophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 生成 (E)-3-(4-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  HASHIMOTO MICHIAKI; IWAYANAGI TAKAO; SHIRAISHI HIROSHI; NONOGAKI SABURO, POLYM. ENG. AND SCI., 26,(1986) N 16, 1090-1095

  摘要：

  DOI：

文献信息

• Hybrid α-bromoacryloylamido chalcones. Design, synthesis and biological evaluation
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Olga Cruz-Lopez、Carlota Lopez Cara、Jan Balzarini、Ernest Hamel、Alessandro Canella、Enrica Fabbri、Roberto Gambari、Giuseppe Basso、Giampietro Viola

  DOI：10.1016/j.bmcl.2009.02.038

  日期：2009.4

  against five cancer cell lines. Such hybrid derivatives demonstrated significantly increased anti-tumor activity compared with the corresponding amino chalcones. The most promising lead molecules were 1k, 1m and 2j, which had the highest activity toward the five cell lines. Flow cytometry with K562 cells showed that the most active compounds resulted in a large proportion of the cells entering in the apoptotic

  查尔酮抗肿瘤特性的研究在过去几年中受到了极大的关注 两个新的大型系列 α-溴丙烯酰氨基查尔酮1a - m和2a - k在其结构中包含一对迈克尔受体，对应于 α-溴丙烯酰合成部分和查尔酮框架的 α,β-不饱和酮系统，并评估其对五种癌细胞系的抗增殖活性。与相应的氨基查耳酮相比，这种杂化衍生物表现出显着增加的抗肿瘤活性。最有前途的先导分子是1k , 1m和2j 。，对五种细胞系的活性最高。K562 细胞的流式细胞术显示，活性最强的化合物导致大部分细胞进入凋亡亚 G0-G1 峰。此外，化合物1k通过线粒体途径诱导细胞凋亡并激活 caspase-3。