5-氨基-4-溴-2-甲基-2H-吡嗪-3-酮 | 65269-63-8

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氨基-4-溴-2-甲基-2H-吡嗪-3-酮
• 英文名称: 5-amino-4-bromo-2-methyl-2H-pyridazin-3-one
• 英文别名: 5-amino-4-bromo-2-methylpyridazin-3-one
• CAS: 65269-63-8
• 化学式: C₅H₆BrN₃O
• 分子量: 204.026
• InChiKey: BQJZZCXHPXTYBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (S)-2-(2,6-dichloro-benzoylamino)-3-(4-boronophenyl)-propionic acid 、 5-氨基-4-溴-2-甲基-2H-吡嗪-3-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 (2S)-3-[4-(5-amino-2-methyl-3-oxo-2,3-dihydropyridazin-4-yl)phenyl]-2-[(2,6-dichlorophenyl)formamido]propanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Pyridazinone-Based α₄ Integrin Receptor Antagonists

  摘要：

  A novel series of pyridazinone-functionalized phenylalanine analogues was prepared and evaluated for inhibition of cellular adhesion mediated by alpha(4)beta(1)/VCAM-1 and alpha(4)beta(7)/MAdCAM-1 interactions. Concise syntheses were developed and applied for exploration of structure-activity relationships pertaining to the pyridazinone ring as well as the N-acyl phenylalanine scaffold. Potent dual antagonists of alpha(4)beta(1) and alpha(4)beta(7) were generated from an amide subseries; antagonists selective for alpha(4)beta(7) were identified from urea and carbamate-based subseries. The pharmacokinetic properties of selected members of the series have been determined in rats and demonstrate that the use of ester prodrugs and alterations to the amide linkage can lead to improved oral bioavailability in this series. An alpha(4),beta(7)-selective member of the carbamate subseries (36c), upon oral admininstration, demonstrated in vivo efficacy in the mouse DSS colitis model.

  DOI：

  10.1021/jm060031q
• 作为产物：
  描述：

  4,5-二溴-2-甲基-2H-吡嗪-3-酮 在 氨 作用下， 以 水 为溶剂， 反应 6.0h， 以34%的产率得到5-氨基-4-溴-2-甲基-2H-吡嗪-3-酮
  参考文献：
  名称：

  Suzuki-aza-Wittig、Suzuki-缩合和aza-Wittig-电环合环串联反应合成含氮稠环系统

  摘要：

  我们描述了 Suzuki-aza-Wittig、Suzuki-缩合和 aza-Wittig 电环闭合反应的串联组合，用于合成新的哒嗪基 [4,5-c] 异喹啉酮、哒嗪基 [4,5-c] 喹啉酮和嘧啶基 [5， 4-c]喹啉衍生物。

  DOI：

  10.3998/ark.5550190.0012.a19

文献信息

• PILGRAMM K. H.; POLLARD G. E., J. HETEROCYCL. CHEM. <JHTC-AD>, 1977, 14, NO 6, 1039-1043
  作者：PILGRAMM K. H.、 POLLARD G. E.

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of Novel Pyridazinone-Based α₄ Integrin Receptor Antagonists
  作者：Yong Gong、J. Kent Barbay、Alexey B. Dyatkin、Tamara A. Miskowski、Edward S. Kimball、Stephen M. Prouty、M. Carolyn Fisher、Rosemary J. Santulli、Craig R. Schneider、Nathaniel H. Wallace、Scott A. Ballentine、William E. Hageman、John A. Masucci、Bruce E. Maryanoff、Bruce P. Damiano、Patricia Andrade-Gordon、Dennis J. Hlasta、Pamela J. Hornby、Wei He

  DOI：10.1021/jm060031q

  日期：2006.6.1

  A novel series of pyridazinone-functionalized phenylalanine analogues was prepared and evaluated for inhibition of cellular adhesion mediated by alpha(4)beta(1)/VCAM-1 and alpha(4)beta(7)/MAdCAM-1 interactions. Concise syntheses were developed and applied for exploration of structure-activity relationships pertaining to the pyridazinone ring as well as the N-acyl phenylalanine scaffold. Potent dual antagonists of alpha(4)beta(1) and alpha(4)beta(7) were generated from an amide subseries; antagonists selective for alpha(4)beta(7) were identified from urea and carbamate-based subseries. The pharmacokinetic properties of selected members of the series have been determined in rats and demonstrate that the use of ester prodrugs and alterations to the amide linkage can lead to improved oral bioavailability in this series. An alpha(4),beta(7)-selective member of the carbamate subseries (36c), upon oral admininstration, demonstrated in vivo efficacy in the mouse DSS colitis model.
• Suzuki-aza-Wittig, Suzuki-condensation and aza-Wittig-electrocyclic ring-closure tandem reactions for synthesis of fused nitrogen-containing ring systems
  作者：Gábor Krajsovszky、László Károlyházy、Petra Dunkel、Sándor Boros、Antonino Grillo、Péter Mátyus

  DOI：10.3998/ark.5550190.0012.a19

  日期：——

  We describe tandem combinations of Suzuki-aza-Wittig, Suzuki-condensation and aza-Wittigelectrocyclic ring closure reactions for the synthesis of new pyridazino[4,5-c]isoquinolinone, pyridazino[4,5-c]quinolinone and pyrimido[5,4-c]quinoline derivatives.

  我们描述了 Suzuki-aza-Wittig、Suzuki-缩合和 aza-Wittig 电环闭合反应的串联组合，用于合成新的哒嗪基 [4,5-c] 异喹啉酮、哒嗪基 [4,5-c] 喹啉酮和嘧啶基 [5， 4-c]喹啉衍生物。