N-(3,4-dimethylphenyl)-3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonamide | 901752-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-(3,4-dimethylphenyl)-3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonamide
• 英文别名: NCGC00187744；N-(3,4-dimethylphenyl)-3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonamide；N-(3,4-dimethylphenyl)-3-methyl-2-oxo-1,3-benzoxazole-6-sulfonamide
• CAS: 901752-69-0
• 化学式: C₁₆H₁₆N₂O₄S
• mdl: MFCD05718608
• 分子量: 332.38
• InChiKey: WOHFPYQPLYBUJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二甲基苯胺 、 3-甲基-2-氧代-2,3-二氢-1,3-苯并唑-6-磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(3,4-dimethylphenyl)-3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonamide
  参考文献：
  名称：

  2-Oxo-N-aryl-1,2,3,4-tetrahydroquinoline-6-sulfonamides as activators of the tumor cell specific M2 isoform of pyruvate kinase

  摘要：

  Compared to normal differentiated cells, cancer cells have altered metabolic regulation to support biosynthesis and the expression of the M2 isozyme of pyruvate kinase (PKM2) plays an important role in this anabolic metabolism. While the M1 isoform is a highly active enzyme, the alternatively spliced M2 variant is considerably less active and expressed in tumors. While the exact mechanism by which decreased pyruvate kinase activity contributes to anabolic metabolism remains unclear, it is hypothesized that activation of PKM2 to levels seen with PKM1 may promote a metabolic program that is not conducive to cell proliferation. Here we report the third chemotype in a series of PKM2 activators based on the 2-oxo-N-aryl-1,2,3,4-tetrahydroquinoline-6-sulfonamide scaffold. The synthesis, structure activity relationships, selectivity and notable physiochemical properties are described. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.08.114

文献信息

• PKM2 ACTIVATORS FOR USE IN THE TREATMENT OF CANCER
  申请人：Agios Pharmaceuticals, Inc.

  公开号：EP2427441B1

  公开（公告）日：2016-12-14
• PKM2 MODULATORS FOR USE IN THE TREATMENT OF CANCER
  申请人：Salituro Francesco G.

  公开号：US20120122849A1

  公开（公告）日：2012-05-17

  Compounds that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are pharmaceutical compositions comprising the compounds, and methods of using the compounds in the treatment of cancer.
• ACTIVATORS OF PYRUVATE KINASE M2 AND METHODS OF TREATING DISEASE
  申请人：Kung Charles

  公开号：US20140249150A1

  公开（公告）日：2014-09-04

  The invention described herein features methods, compositions, and kits that utilize activators of pyruvate kinase M2 (PKM2) for the treatment or amelioration of disorders related to PKM2 function and characterized by abnormally low levels of serine.
• US8501953B2
  申请人：——

  公开号：US8501953B2

  公开（公告）日：2013-08-06
• [EN] PMK2 MODULATORS FOR USE IN THE TREATMENT OF CANCER<br/>[FR] INHIBITEURS DE LA PKM2 DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DU CANCER
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2010129596A1

  公开（公告）日：2010-11-11

  Compounds that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are pharmaceutical compositions comprising the compounds, and methods of using the compounds in the treatment of cancer.