3-(3-bromo-2-oxopropyl)-1,5,5-trimethylimidazolidine-2,4-dione | 220615-58-7

• 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: 3-(3-bromo-2-oxopropyl)-1,5,5-trimethylimidazolidine-2,4-dione
• 英文别名: 1-bromo-3-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)propan-2-one
• CAS: 220615-58-7
• 化学式: C₉H₁₃BrN₂O₃
• 分子量: 277.118
• InChiKey: SKCQKTIUCVINNH-UHFFFAOYSA-N

物化性质

• 沸点：
  329.2±48.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-bromo-2-oxopropyl)-1,5,5-trimethylimidazolidine-2,4-dione 在 盐酸 、 吡啶硼烷 、 盐酸羟胺 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(1-(((3'-cyano(1,1'-biphenyl)-4-yl)oxy)methyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl)-N-hydroxyformamide
  参考文献：
  名称：

  Discovery and characterization of the potent, selective and orally bioavailable MMP inhibitor ABT-770

  摘要：

  Modification of the biphenyl portion of MMP inhibitor 2a gave analogue 2i which is greater than 1000-fold selective against MMP-2 versus MMP-1. The stereospecific synthesis of both enantiomers of 2i was achieved beginning with (S)- or (R)-benzyl glycidyl ether. The (S)-enantiomer, 11 (ABT-770), is orally bioavailable and efficacious in an in vivo model of tumor growth. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00032-4
• 作为产物：
  描述：

  1,5,5-三甲基海因 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3-(3-bromo-2-oxopropyl)-1,5,5-trimethylimidazolidine-2,4-dione
  参考文献：
  名称：

  Discovery and characterization of the potent, selective and orally bioavailable MMP inhibitor ABT-770

  摘要：

  Modification of the biphenyl portion of MMP inhibitor 2a gave analogue 2i which is greater than 1000-fold selective against MMP-2 versus MMP-1. The stereospecific synthesis of both enantiomers of 2i was achieved beginning with (S)- or (R)-benzyl glycidyl ether. The (S)-enantiomer, 11 (ABT-770), is orally bioavailable and efficacious in an in vivo model of tumor growth. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00032-4

文献信息

• Reverse hydroxamate inhibitors of matrix metalloproteinases
  申请人：Abbott Laboratories

  公开号：US06294573B1

  公开（公告）日：2001-09-25

  Compounds having the formula are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.

  具有以下化学式的化合物是基质金属蛋白酶抑制剂。还公开了抑制基质金属蛋白酶的组合物和方法，用于在哺乳动物中抑制基质金属蛋白酶。
• Metalloproteinase inhibitors
  申请人：——

  公开号：US20040127528A1

  公开（公告）日：2004-07-01

  Compounds of the formula (I) wherein z is SO 2 or SO, useful as metalloproteinase inhibitors, especially as inhibitors of MMP12.

  式(I)的化合物，其中z为SO2或SO，可用作金属蛋白酶抑制剂，特别是MMP12的抑制剂。
• Metalloproteinase Inhibitors
  申请人：Eriksson Anders

  公开号：US20080306065A1

  公开（公告）日：2008-12-11

  Compounds of the formula (I) wherein z is SO 2 or SO, useful as metalloproteinase inhibitors, especially as inhibitors of MMP12.

  公式为（I）的化合物，其中z为SO2或SO，可用作金属蛋白酶抑制剂，特别是作为MMP12的抑制剂。
• Hydantoin derivatives as MMP inhibitors
  申请人：AstraZeneca AB

  公开号：EP1676846A2

  公开（公告）日：2006-07-05

  Compounds of the formula I wherein z is SO2 or SO, useful as metalloproteinase inhibitors, especially as inhibitors of MMP12.

  式 I 的化合物 其中 z 为 SO2 或 SO，可用作金属蛋白酶抑制剂，尤其是 MMP12 的抑制剂。
• Phenoxyphenyl Sulfone <i>N</i>-Formylhydroxylamines (Retrohydroxamates) as Potent, Selective, Orally Bioavailable Matrix Metalloproteinase Inhibitors
  作者：Carol K. Wada、James H. Holms、Michael L. Curtin、Yujia Dai、Alan S. Florjancic、Robert B. Garland、Yan Guo、H. Robin Heyman、Jamie R. Stacey、Douglas H. Steinman、Daniel H. Albert、Jennifer J. Bouska、Ildiko N. Elmore、Carole L. Goodfellow、Patrick A. Marcotte、Paul Tapang、Douglas W. Morgan、Michael R. Michaelides、Steven K. Davidsen

  DOI：10.1021/jm0103920

  日期：2002.1.1

  A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was accompanied by a loss of selectivity for inhibition of MMP-2 and -9 over MMP-1 and diminished oral exposure. Replacement of the biphenyl P1' substituent with a phenoxyphenyl group provided compounds that are highly selective for inhibition of MMP-2 and -9 over MMP-1. Optimization of the substituent adjacent to the retrohydroxamate center in this series led to the clinical candidate ABT-518 (6), a highly potent, selective, orally bioavailable MMP inhibitor that has been shown to significantly inhibit tumor growth in animal cancer models.