Methyl 3-[(3-fluorophenyl)sulfonylamino]benzoate | 923911-01-7

• 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: Methyl 3-[(3-fluorophenyl)sulfonylamino]benzoate
• CAS: 923911-01-7
• 化学式: C₁₄H₁₂FNO₄S
• 分子量: 309.318
• InChiKey: AXEFBWOHDPCDEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-[(3-fluorophenyl)sulfonylamino]benzoate 在 N-溴代丁二酰亚胺(NBS) 、 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-3-fluorobenzenesulfonamide
  参考文献：
  名称：

  Development of potent B-RafV600E inhibitors containing an arylsulfonamide headgroup

  摘要：

  A potent series of inhibitors against the B-RafV600E kinase have been developed that show excellent activity in cellular assays and good oral bioavailability in rats. The key structural features of the series are an arylsulfonamide headgroup, a thiazole core, and a fluorine ortho to the sulfonamide nitrogen. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.021
• 作为产物：
  描述：

  间氨基苯甲酸 在 吡啶 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 3-[(3-fluorophenyl)sulfonylamino]benzoate
  参考文献：
  名称：

  Development of potent B-RafV600E inhibitors containing an arylsulfonamide headgroup

  摘要：

  A potent series of inhibitors against the B-RafV600E kinase have been developed that show excellent activity in cellular assays and good oral bioavailability in rats. The key structural features of the series are an arylsulfonamide headgroup, a thiazole core, and a fluorine ortho to the sulfonamide nitrogen. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.021

文献信息

• Discovery of Dabrafenib: A Selective Inhibitor of Raf Kinases with Antitumor Activity against B-Raf-Driven Tumors
  作者：Tara R. Rheault、John C. Stellwagen、George M. Adjabeng、Keith R. Hornberger、Kimberly G. Petrov、Alex G. Waterson、Scott H. Dickerson、Robert A. Mook、Sylvie G. Laquerre、Alastair J. King、Olivia W. Rossanese、Marc R. Arnone、Kimberly N. Smitheman、Laurie S. Kane-Carson、Chao Han、Ganesh S. Moorthy、Katherine G. Moss、David E. Uehling

  DOI：10.1021/ml4000063

  日期：2013.3.14

  Hyperactive signaling of the MAP kinase pathway resulting from the constitutively active B-Raf(v600E) mutated enzyme has been observed in a number of human tumors, including melanomas. Herein we report the discovery and biological evaluation of GSK2118436, a selective inhibitor of Raf kinases with potent in vitro activity in oncogenic B-Raf-driven melanoma and colorectal carcinoma cells and robust in vivo antitumor and pharmacodynamic activity in mouse models of B-Raf(v600E) human melanoma. GSK2118436 was identified as a development candidate, and early clinical results have shown significant activity in patients with B-Raf mutant melanoma.