4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}benzenesulfonamide | 1114991-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}benzenesulfonamide
• 英文别名: 4-(4-(naphthalen-2-yl)pyrimidin-2-ylamino)benzenesulfonamide；4-[(4-naphthalen-2-ylpyrimidin-2-yl)amino]benzenesulfonamide
• CAS: 1114991-95-5
• 化学式: C₂₀H₁₆N₄O₂S
• 分子量: 376.439
• InChiKey: SXFKMLRIZKPLQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-chloro-4-[2-naphthyl]pyrimidine 、 磺胺 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以68%的产率得到4-{[4-(2-naphthyl)pyrimidin-2-yl]amino}benzenesulfonamide
  参考文献：
  名称：

  (1-(4-(Naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine: A Wingless β-Catenin Agonist That Increases Bone Formation Rate

  摘要：

  A high-throughput screening campaign to discover small molecule leads for the treatment of bone disorders concluded with the discovery of a compound with a 2-aminopyrimidine template that targeted the Wnt beta-catenin cellular messaging system. Hit-to-lead in vitro optimization for target activity and molecular properties led to the discovery of (1-(4-(naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine (5, WAY-262611). Compound 5 has excellent pharmacokinetic properties and showed a dose dependent increase in the trabecular bone formation rate in ovariectomized rats following oral administration.

  DOI：

  10.1021/jm9014197

文献信息

• PYRIMIDINE SULFONAMIDE ANALOGS AND THEIR USE AS AGONISTS OF THE WNT-BETA-CATENIN CELLULAR MESSAGING SYSTEM
  申请人：Hauze Diane Barbara

  公开号：US20090048282A1

  公开（公告）日：2009-02-19

  The present invention relates to pyrimidine sulfonamide analogs, methods of making pyrimidine sulfonamide analogs, compositions comprising a pyrimidine sulfonamide analog, and methods for treating canonical Wnt-β-catenin cellular messaging system-related disorders comprising administering to a subject in need thereof an effective amount of a pyrimidine sulfonamide analog.

  本发明涉及嘧啶磺胺类似物，制备嘧啶磺胺类似物的方法，包含嘧啶磺胺类似物的组合物，以及治疗与经典Wnt-β-连环蛋白细胞信使系统相关的疾病的方法，包括向需要的受试者施用有效量的嘧啶磺胺类似物。
• (1-(4-(Naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine: A Wingless β-Catenin Agonist That Increases Bone Formation Rate
  作者：Jeffrey C. Pelletier、Joseph T. Lundquist、Adam M. Gilbert、Nipa Alon、Frederick J. Bex、Bheem M. Bhat、Mattew G. Bursavich、Valerie E. Coleburn、Luciana A. Felix、Daniel M. Green、Paula Green、Diane B. Hauze、Yogendra P. Kharode、Ho-Sun Lam、Susan R. Lockhead、Ronald L. Magolda、Jeanne J. Matteo、John F. Mehlmann、Colleen Milligan、Richard J. Murrills、Jennifer Pirrello、Sally Selim、Michael C. Sharp、Ray J. Unwalla、Matthew D. Vera、Jay E. Wrobel、Paul Yaworsky、Peter V. N. Bodine

  DOI：10.1021/jm9014197

  日期：2009.11.26

  A high-throughput screening campaign to discover small molecule leads for the treatment of bone disorders concluded with the discovery of a compound with a 2-aminopyrimidine template that targeted the Wnt beta-catenin cellular messaging system. Hit-to-lead in vitro optimization for target activity and molecular properties led to the discovery of (1-(4-(naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine (5, WAY-262611). Compound 5 has excellent pharmacokinetic properties and showed a dose dependent increase in the trabecular bone formation rate in ovariectomized rats following oral administration.