N-(7-[4-fluorophenyl]quinazolin-4-yl)-4-((1-(phenylthio)ethan-2-yl)amino)-3-nitrobenzenesulfonamide | 1197199-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(7-[4-fluorophenyl]quinazolin-4-yl)-4-((1-(phenylthio)ethan-2-yl)amino)-3-nitrobenzenesulfonamide
• 英文别名: N-(7-(4-fluorophenyl)quinazolin-4-yl)-3-nitro-4-(2-(phenylthio)ethylamino) benzenesulfonamide；N-(7-(4-fluorophenyl)quinazolin-4-yl)-3-nitro-4-(2-(phenylthio)ethylamino)benzenesulfonamide；N-[7-(4-fluorophenyl)quinazolin-4-yl]-3-nitro-4-(2-phenylsulfanylethylamino)benzenesulfonamide
• CAS: 1197199-79-3
• 化学式: C₂₈H₂₂FN₅O₄S₂
• 分子量: 575.644
• InChiKey: WKCIAPXBSZRGIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-硝基-4-氯苯磺酰胺 在 四(三苯基膦)钯 copper(l) iodide 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 72.75h， 生成 N-(7-[4-fluorophenyl]quinazolin-4-yl)-4-((1-(phenylthio)ethan-2-yl)amino)-3-nitrobenzenesulfonamide
  参考文献：
  名称：

  [EN] ARYLSULFONAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  [FR] COMPOSÉS ARYLSULFONAMIDES, COMPOSITIONS ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2009143246A3

文献信息

• Quinazoline Sulfonamides as Dual Binders of the Proteins B-Cell Lymphoma 2 and B-Cell Lymphoma Extra Long with Potent Proapoptotic Cell-Based Activity
  作者：Brad E. Sleebs、Peter E. Czabotar、Wayne J. Fairbrother、W. Douglas Fairlie、John A. Flygare、David C. S. Huang、Wilhelmus J. A. Kersten、Michael F. T. Koehler、Guillaume Lessene、Kym Lowes、John P. Parisot、Brian J. Smith、Morey L. Smith、Andrew J. Souers、Ian P. Street、Hong Yang、Jonathan B. Baell

  DOI：10.1021/jm101596e

  日期：2011.3.24

  ABT-737 and ABT-263 are potent inhibitors of the BH3 antiapoptotic proteins, Bcl-x(L) and Bcl-2. This class of putative anticancer agents invariantly contains an acylsulfonamide core. We have designed and synthesized a series of novel quinazoline-based inhibitors of Bcl-2 and Bcl-xL that contain a heterocyclic alternative to the acylsulfonamide. These compounds exhibit submicromolar, mechanism-based activity in human small-cell lung carcinoma cell lines in the presence of 10% human serum. This comprises the first successful demonstration of a quinazoline sulfonamide core serving as an effective benzoylsulfonamide bioisostere. Additionally, these novel quinazolines comprise only the second known class of Bcl-2 family protein inhibitors to induce mechanism-based cell death.
• ARYLSULFONAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：Genentech, Inc.

  公开号：EP2279174A2

  公开（公告）日：2011-02-02
• [EN] ARYLSULFONAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS ARYLSULFONAMIDES, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：GENENTECH INC

  公开号：WO2009143246A3

  公开（公告）日：2010-04-29