(E)-N-(3-(3-(4-hydroxyphenyl)acryloyl)phenyl)benzamide | 1590366-82-7

• 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)-N-(3-(3-(4-hydroxyphenyl)acryloyl)phenyl)benzamide
• 英文别名: N-[3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl]benzamide
• CAS: 1590366-82-7
• 化学式: C₂₂H₁₇NO₃
• 分子量: 343.382
• InChiKey: AKFHJWKOMSTNFY-SDNWHVSQSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  489.2±45.0 °C(predicted)
• 密度：
  1.285±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3-乙酰苯基)苯甲酰胺 、 对羟基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以44%的产率得到(E)-N-(3-(3-(4-hydroxyphenyl)acryloyl)phenyl)benzamide
  参考文献：
  名称：

  Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes

  摘要：

  Four sets of rationally designed chalcones were prepared for evaluation of their antiobesity, antioxidant and cytotoxicity activities. These sets include nine oleoyl chalcones as mimics of oleoyl estrone, three monohydroxy chalcones (chalcone ligands), Schiff base-derived chalcones and four copper as well as zinc complexes. Oleoyl chalcones 4d, 4e and particularly 6a as an isosteric isomer of oleoyl estrone, were as active as Orlistat on weight loss and related metabolic parameters using male SD rats in vivo. Chalcone ligands 10a-c and Schiff base-derived chalcones 11 and 14a,b were weakly antioxidants, while, the copper and zinc complexes 15a-d were good antioxidants with zinc chelates 15b,d being more active than their copper analogues 15a,c in vitro. Compounds 10c and 14a showed good cytotoxicity activities as Doxorubicin against PC3 cancer cell line in vitro, while, the copper complex 15c showed promising activity with IC50 value of 5.95 mu M. The estimated IC50 value for Doxorubicin was 8.7 mu M. Chalcones 14a,b are bifunctional probes for potential investigations in cancer diagnosis and radiotherapy by complexation with Gd3+ or metal radioisotopes followed by posttranslation of Shiga toxin B-subunits that target globotriosyl ceramide expressing cancer cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.021

文献信息

• Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes
  作者：Mohamed Ramadan El Sayed Aly、Hamadah Hamadah Abd El Razek Fodah、Sherif Yousef Saleh

  DOI：10.1016/j.ejmech.2014.02.021

  日期：2014.4

  Four sets of rationally designed chalcones were prepared for evaluation of their antiobesity, antioxidant and cytotoxicity activities. These sets include nine oleoyl chalcones as mimics of oleoyl estrone, three monohydroxy chalcones (chalcone ligands), Schiff base-derived chalcones and four copper as well as zinc complexes. Oleoyl chalcones 4d, 4e and particularly 6a as an isosteric isomer of oleoyl estrone, were as active as Orlistat on weight loss and related metabolic parameters using male SD rats in vivo. Chalcone ligands 10a-c and Schiff base-derived chalcones 11 and 14a,b were weakly antioxidants, while, the copper and zinc complexes 15a-d were good antioxidants with zinc chelates 15b,d being more active than their copper analogues 15a,c in vitro. Compounds 10c and 14a showed good cytotoxicity activities as Doxorubicin against PC3 cancer cell line in vitro, while, the copper complex 15c showed promising activity with IC50 value of 5.95 mu M. The estimated IC50 value for Doxorubicin was 8.7 mu M. Chalcones 14a,b are bifunctional probes for potential investigations in cancer diagnosis and radiotherapy by complexation with Gd3+ or metal radioisotopes followed by posttranslation of Shiga toxin B-subunits that target globotriosyl ceramide expressing cancer cells. (C) 2014 Elsevier Masson SAS. All rights reserved.