4-bromo-3-(methylsulfonyl)benzoic acid | 158608-01-6

• 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: 4-bromo-3-(methylsulfonyl)benzoic acid
• 英文别名: 4-Bromo-3-methanesulfonylbenzoic acid；4-bromo-3-methylsulfonylbenzoic acid
• CAS: 158608-01-6
• 化学式: C₈H₇BrO₄S
• mdl: MFCD11179997
• 分子量: 279.111
• InChiKey: LVVHVWLMNKOUFR-UHFFFAOYSA-N

物化性质

• 沸点：
  492.9±45.0 °C(Predicted)
• 密度：
  1.745±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氟苯硼酸 、 4-bromo-3-(methylsulfonyl)benzoic acid 在 4-二甲氨基吡啶 、 potassium phosphate 、 (2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (R)-4'-fluoro-2-(methylsulfonyl)-N-(4-(4-morpholino-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonyl)biphenyl-4-carboxamide
  参考文献：
  名称：

  Discovery and optimization of covalent Bcl-xL antagonists

  摘要：

  Over the last ten years, targeted covalent inhibition has become a key discipline within medicinal chemistry research, most notably in the development of oncology therapeutics. One area where this approach is under-represented, however, is in targeting protein-protein interactions. This is primarily because these hydrophobic interfaces lack appropriately located cysteine residues to allow for standard conjugate addition chemistry. Herein, we report our development of the first covalent inhibitors of the antiapoptotic protein B-cell lymphoma extra-large (Bcl-xL), utilizing a sulfonyl fluoride (SF) warhead to selectively covalently modify tyrosine 101 of the BH3 domain-binding groove. These compounds display time-dependent inhibition in a biochemical assay and are cellularly active (U266B1). In addition, compound 7 was further elaborated to generate a chemical-biology probe molecule, which may find utility in understanding the intricacies of Bcl-xL biology.

  DOI：

  10.1016/j.bmcl.2019.126682

文献信息

• Heterobicyclic metalloprotease inhibitors
  申请人：Steeneck Christoph

  公开号：US20070155738A1

  公开（公告）日：2007-07-05

  The present invention relates generally to amide group containing pharmaceutical agents, and in particular, to amide containing heterobicyclic metalloprotease inhibitor compounds. More particularly, the present invention provides a new class of heterobicyclic MMP-13 inhibiting and MMP-3 inhibiting compounds, that exhibit an increased potency in relation to currently known MMP-13 and MMP-3 inhibitors.
• Heterobicyclic Metalloprotease Inhibitors
  申请人：STEENECK Christoph

  公开号：US20090312312A1

  公开（公告）日：2009-12-17

  The present invention relates generally to amide group containing pharmaceutical agents, and in particular, to amide containing heterobicyclic metalloprotease inhibitor compounds. More particularly, the present invention provides a new class of heterobicyclic MMP-13 inhibiting and MMP-3 inhibiting compounds, that exhibit an increased potency in relation to currently known MMP-13 and MMP-3 inhibitors.
• HETEROBICYCLIC METALLOPROTEASE INHIBITORS
  申请人：Steeneck Christoph

  公开号：US20120015920A1

  公开（公告）日：2012-01-19

  The present invention relates generally to amide group containing pharmaceutical agents, and in particular, to amide containing heterobicyclic metalloprotease inhibitor compounds. More particularly, the present invention provides a new class of heterobicyclic MMP-13 inhibiting and MMP-3 inhibiting compounds, that exhibit an increased potency in relation to currently known MMP-13 and MMP-3 inhibitors.
• US5747539A
  申请人：——

  公开号：US5747539A

  公开（公告）日：1998-05-05
• US7795245B2
  申请人：——

  公开号：US7795245B2

  公开（公告）日：2010-09-14