N-2-tolyl-4-(2-oxoimidazolidin-1-yl)benzenesulfonamide | 1328953-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-2-tolyl-4-(2-oxoimidazolidin-1-yl)benzenesulfonamide
• 英文别名: N-2-tolyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamide；N-(2-methylphenyl)-4-(2-oxoimidazolidin-1-yl)benzenesulfonamide
• CAS: 1328953-13-4
• 化学式: C₁₆H₁₇N₃O₃S
• 分子量: 331.395
• InChiKey: KGFQYGFVTMWOBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-氯乙基)-3-苯基脲 在 氯磺酸 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 乙腈 为溶剂， 生成 N-2-tolyl-4-(2-oxoimidazolidin-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-activity relationships

  摘要：

  The importance of the bridge linking the two phenyl moieties of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) was assessed using a sulfonamide group, which is a bioisostere of sulfonate and ethenyl groups. Forty one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamide (PIB-SA) derivatives were prepared and biologically evaluated. PIB-SAs exhibit antiproliferative activities at the nanomolar level against sixteen cancer cell lines, block the cell cycle progression in G(2)/M phase, leading to cytoskeleton disruption and anoikis. These results were subjected to CoMFA and CoMSIA analyses to establish quantitative structure-activity relationships. These results evidence that the sulfonate and sulfonamide moieties are reciprocal bioisosteres and that phenylimidazolidin-2-one could mimic the trimethoxyphenyl moiety found in the structure of numerous potent antimicrotubule agents. Finally, compounds 16 and 17 exhibited potent antitumor and antiangiogenic activities on HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membrane similar to CA-4 without significant toxicity for the chick embryos, making this class of compounds a promising class of anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.034

文献信息

• SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS
  申请人：Gaudreault René C.

  公开号：US20120309777A1

  公开（公告）日：2012-12-06

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 7 , R 6 , R 7 , R 8 , R 9 , A, X and Y as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.
• US9034888B2
  申请人：——

  公开号：US9034888B2

  公开（公告）日：2015-05-19
• Substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-activity relationships
  作者：Sébastien Fortin、Lianhu Wei、Emmanuel Moreau、Jacques Lacroix、Marie-France Côté、Éric Petitclerc、Lakshmi P. Kotra、René C. Gaudreault

  DOI：10.1016/j.ejmech.2011.08.034

  日期：2011.11

  The importance of the bridge linking the two phenyl moieties of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) was assessed using a sulfonamide group, which is a bioisostere of sulfonate and ethenyl groups. Forty one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamide (PIB-SA) derivatives were prepared and biologically evaluated. PIB-SAs exhibit antiproliferative activities at the nanomolar level against sixteen cancer cell lines, block the cell cycle progression in G(2)/M phase, leading to cytoskeleton disruption and anoikis. These results were subjected to CoMFA and CoMSIA analyses to establish quantitative structure-activity relationships. These results evidence that the sulfonate and sulfonamide moieties are reciprocal bioisosteres and that phenylimidazolidin-2-one could mimic the trimethoxyphenyl moiety found in the structure of numerous potent antimicrotubule agents. Finally, compounds 16 and 17 exhibited potent antitumor and antiangiogenic activities on HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membrane similar to CA-4 without significant toxicity for the chick embryos, making this class of compounds a promising class of anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.