5-(4-(difluoromethoxy)phenyl)-5-methylimidazolidine-2,4-dione | 316806-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(4-(difluoromethoxy)phenyl)-5-methylimidazolidine-2,4-dione
• 英文别名: 5-[4-(Difluoromethoxy)phenyl]-5-methylimidazolidine-2,4-dione
• CAS: 316806-56-1
• 化学式: C₁₁H₁₀F₂N₂O₃
• mdl: MFCD01124511
• 分子量: 256.209
• InChiKey: AVNWWORDKUNNTP-UHFFFAOYSA-N

物化性质

• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-(difluoromethoxy)phenyl)-5-methylimidazolidine-2,4-dione 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 sodium hydroxide 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二乙二醇二甲醚 为溶剂， 生成
  参考文献：
  名称：

  BMS-201620: a selective beta 3 agonist

  摘要：

  A series of N-(4-hydroxy-3-methylsulfonanilidoethanol)arylglycinamides were prepared and evaluated for their human beta(3) adrenergic receptor agonist activity. SAR studies led to the identification of BMS-201620 (39), a potent beta(3) full agonist (K-i = 93 nM, 93% activation). Based on its favorable safety profile, BMS-201620 was chosen for clinical evaluation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.074
• 作为产物：
  描述：

  氰化钠 、 碳酸氢铵 、 1-[4-(二氟甲氧基)苯基]乙酮 在 碳酸氢铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-(difluoromethoxy)phenyl)-5-methylimidazolidine-2,4-dione
  参考文献：
  名称：

  BMS-201620: a selective beta 3 agonist

  摘要：

  A series of N-(4-hydroxy-3-methylsulfonanilidoethanol)arylglycinamides were prepared and evaluated for their human beta(3) adrenergic receptor agonist activity. SAR studies led to the identification of BMS-201620 (39), a potent beta(3) full agonist (K-i = 93 nM, 93% activation). Based on its favorable safety profile, BMS-201620 was chosen for clinical evaluation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.074

文献信息

• Identification and Profiling of Hydantoins—A Novel Class of Potent Antimycobacterial DprE1 Inhibitors
  作者：Maciej K. Rogacki、Eleni Pitta、Olga Balabon、Sophie Huss、Eva Maria Lopez-Roman、Argyrides Argyrou、Delia Blanco-Ruano、Monica Cacho、Christophe M. L. Vande Velde、Koen Augustyns、Lluis Ballell、David Barros、Robert H. Bates、Fraser Cunningham、Pieter Van der Veken

  DOI：10.1021/acs.jmedchem.8b01356

  日期：2018.12.27

  Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-beta-D-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.
• BMS-201620: a selective beta 3 agonist
  作者：W.N. Washburn、C.-Q. Sun、G. Bisacchi、G. Wu、P.T. Cheng、P.M. Sher、D. Ryono、A.V. Gavai、K. Poss、R.N. Girotra、P.J. McCann、A.B. Mikkilineni、T.C. Dejneka、T.C. Wang、Z. Merchant、M. Morella、C.M. Arbeeny、T.W. Harper、D.A. Slusarchyk、S. Skwish、A.D. Russell、G.T. Allen、B. Tesfamariam、B.H. Frohlich、B.E. Abboa-Offei、M. Cap、T.L. Waldron、R.J. George、D. Young、K.E. Dickinson、A.A. Seymour

  DOI：10.1016/j.bmcl.2004.04.074

  日期：2004.7

  A series of N-(4-hydroxy-3-methylsulfonanilidoethanol)arylglycinamides were prepared and evaluated for their human beta(3) adrenergic receptor agonist activity. SAR studies led to the identification of BMS-201620 (39), a potent beta(3) full agonist (K-i = 93 nM, 93% activation). Based on its favorable safety profile, BMS-201620 was chosen for clinical evaluation. (C) 2004 Elsevier Ltd. All rights reserved.