1-(3,4-Difluorophenyl)-3-(4-methylphenyl)sulfonylurea | 102608-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-Difluorophenyl)-3-(4-methylphenyl)sulfonylurea
• CAS: 102608-00-4
• 化学式: C₁₄H₁₂F₂N₂O₃S
• 分子量: 326.324
• InChiKey: FAYUPQULOODNSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲基苯磺酰异氰酸酯 、 3,4-二氟苯胺 以 甲苯 为溶剂， 以89%的产率得到1-(3,4-Difluorophenyl)-3-(4-methylphenyl)sulfonylurea
  参考文献：
  名称：

  Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships

  摘要：

  A series of diarylsulfonylureas with exceptionally broad-spectrum activity against syngeneic rodent solid tumors in vivo is described. Their discovery resulted from a program dedicated to in vivo screening for novel oncolytics in solid tumor models, rather than traditional ascites leukemia models. The structures, oral efficacy, side-effect profile, and mechanism of action of these sulfonylureas appear to be distinct from previously known classes of oncolytics. An extensive series of analogues was prepared to probe structure-activity relationships (SAR), with particular focus on the substituent patterns of each aryl domain. Quantitative analysis of these substituent SARs, using the method of cluster significance analysis, showed the lipophilicity of the substituents to be the dominant determinant of activity. One compound from the series, LY186641 (104, sulofenur), has progressed to Phase I clinical trials as an antitumor drug.

  DOI：

  10.1021/jm00171a013

文献信息

• HOWBERT, J. JEFFRY;GROSSMAN, C. SUE;CROWELL, THOMAS A.;RIEDER, BRENT J.;H+, J. MED. CHEM., 33,(1990) N, C. 2393-2407
  作者：HOWBERT, J. JEFFRY、GROSSMAN, C. SUE、CROWELL, THOMAS A.、RIEDER, BRENT J.、H+

  DOI：——

  日期：——
• Improvements in or relating to benzenesulfonamido derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0166615B1

  公开（公告）日：1993-05-26
• COMPOSITIONS AND METHODS FOR TREATING FRIEDREICH'S ATAXIA
  申请人：Testi Roberto

  公开号：US20130109658A1

  公开（公告）日：2013-05-02

  A method of treating Friedreich's Ataxia with compounds of formula I including pharmaceutically acceptable salts, tautomers or stereoisomers of compounds of formula Lp.
• US8703749B2
  申请人：——

  公开号：US8703749B2

  公开（公告）日：2014-04-22
• Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships
  作者：J. Jeffry Howbert、C. Sue Grossman、Thomas A. Crowell、Brent J. Rieder、Richard W. Harper、Kenneth E. Kramer、Eddie V. Tao、James Aikins、Gerald A. Poore

  DOI：10.1021/jm00171a013

  日期：1990.9

  A series of diarylsulfonylureas with exceptionally broad-spectrum activity against syngeneic rodent solid tumors in vivo is described. Their discovery resulted from a program dedicated to in vivo screening for novel oncolytics in solid tumor models, rather than traditional ascites leukemia models. The structures, oral efficacy, side-effect profile, and mechanism of action of these sulfonylureas appear to be distinct from previously known classes of oncolytics. An extensive series of analogues was prepared to probe structure-activity relationships (SAR), with particular focus on the substituent patterns of each aryl domain. Quantitative analysis of these substituent SARs, using the method of cluster significance analysis, showed the lipophilicity of the substituents to be the dominant determinant of activity. One compound from the series, LY186641 (104, sulofenur), has progressed to Phase I clinical trials as an antitumor drug.