N-(4-((1Z,2E)-1-(hydroxyimino)-3-(4-nitrophenyl)allyl)phenyl)-4-methylbenzenesulfonamide

• 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: N-(4-((1Z,2E)-1-(hydroxyimino)-3-(4-nitrophenyl)allyl)phenyl)-4-methylbenzenesulfonamide
• 英文别名: N-[4-[(Z)-N-hydroxy-C-[(E)-2-(4-nitrophenyl)ethenyl]carbonimidoyl]phenyl]-4-methylbenzenesulfonamide
• 化学式: C₂₂H₁₉N₃O₅S
• 分子量: 437.476
• InChiKey: AXZAIGLHRJHWTF-LVBPOWAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-N-(4-(3-(4-nitrophenyl)acryloyl)phenyl)-4-methylbenzenesulfonamide 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以63.76%的产率得到N-(4-((1Z,2E)-1-(hydroxyimino)-3-(4-nitrophenyl)allyl)phenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis, anticancer and radiosensitizing evaluation of some novel sulfonamide derivatives

  摘要：

  In this study, novel series of sulfonamide derivatives were synthesized starting from 2-cyanoacetyl) hydrazono)ethyl)phenyl)benzenesulfonamide 4a and 2-cyanoacetyl)hydrazono)ethyl)phenyl)-4-methylbenzenesulfonamide 4b. Different biologically active moieties as pyrazol, thiophene, pyridine and pyrimidines were introduced in order to investigate their in-vitro anticancer activity, in addition to a novel series of sulfonamide chalcones were synthesized from the reported 4-acetyl-N-(P-tolyl) benze-nesulfonamide 3b. The newly synthesized sulfonamide derivatives were characterized by FT-IR, H-1 NMR, C-13 NMR, mass spectroscopy and elemental analyses and were tested for their in-vitro anticancer activity against human tumor liver cell line (HEPG-2). The most potent compounds in this study were compounds 4a, 4b, 5a, 6a, 6b, 8, 9, 11, 13, 18 and 19 which showed higher activity than doxorubicin with IC50 ranging from 11.0 to 31.8 mu M. Additionally, eight compounds among the most potent were evaluated for their ability to enhance the cell killing effect of gamma-radiation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.036

文献信息

• Synthesis, anticancer and radiosensitizing evaluation of some novel sulfonamide derivatives
  作者：Mostafa M. Ghorab、Fatma A. Ragab、Helmy I. Heiba、Marwa G. El-Gazzar、Sally S. Zahran

  DOI：10.1016/j.ejmech.2015.01.036

  日期：2015.3

  In this study, novel series of sulfonamide derivatives were synthesized starting from 2-cyanoacetyl) hydrazono)ethyl)phenyl)benzenesulfonamide 4a and 2-cyanoacetyl)hydrazono)ethyl)phenyl)-4-methylbenzenesulfonamide 4b. Different biologically active moieties as pyrazol, thiophene, pyridine and pyrimidines were introduced in order to investigate their in-vitro anticancer activity, in addition to a novel series of sulfonamide chalcones were synthesized from the reported 4-acetyl-N-(P-tolyl) benze-nesulfonamide 3b. The newly synthesized sulfonamide derivatives were characterized by FT-IR, H-1 NMR, C-13 NMR, mass spectroscopy and elemental analyses and were tested for their in-vitro anticancer activity against human tumor liver cell line (HEPG-2). The most potent compounds in this study were compounds 4a, 4b, 5a, 6a, 6b, 8, 9, 11, 13, 18 and 19 which showed higher activity than doxorubicin with IC50 ranging from 11.0 to 31.8 mu M. Additionally, eight compounds among the most potent were evaluated for their ability to enhance the cell killing effect of gamma-radiation. (C) 2015 Elsevier Masson SAS. All rights reserved.