2-[(3-Bromobenzoyl)amino]propanoic acid | 209916-18-7

• 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: 2-[(3-Bromobenzoyl)amino]propanoic acid
• CAS: 209916-18-7
• 化学式: C₁₀H₁₀BrNO₃
• mdl: MFCD03273220
• 分子量: 272.098
• InChiKey: KGZCLKKCXYCFBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(3-Bromobenzoyl)amino]propanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以92%的产率得到2-(3-bromophenyl)-4-methyl-4H-1,3-oxazol-5-one
  参考文献：
  名称：

  的对称合成2,2'，4,4'-四取代[4,4'- bioxazole] -5,5-'（4 ħ，4' ħ） -二酮和它们与一些亲核试剂反应

  摘要：

  几个对称2,2'，4,4'-四取代[4,4'- bioxazole] -5,5-'（4 ħ，4' ħ） -二酮1A-F 5（4 dehydrodimerization获得ħ） -恶唑酮2a-f。建立了四个的配置。1个通过X射线晶体学rac - 1c进行分析，三个rac - 1a，meso - 1a和rac - 1b通过1 H nmr光谱对其衍生物进行分析。加热后，生物恶唑酮被异构化，可能是由于4,4'-碳的断裂碳键形成自由基，然后重组。交叉实验的结果与该异构化反应的自由基性质一致。用甲醇和胺亲核试剂处理三种生物恶唑酮rac - 1a，meso - 1a和rac - 1c，可得到α，α'-脱氢二聚氨基酸的酯和酰胺衍生物7-11。

  DOI：

  10.1002/jhet.5570350210
• 作为产物：
  描述：

  Methyl 4-(3-bromophenyl)-2-methyl-4-oxobutanoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-[(3-Bromobenzoyl)amino]propanoic acid
  参考文献：
  名称：

  Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity

  摘要：

  A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[ 3-( 1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC(50)s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21(waf). Compound 5x displays efficacy in human tumor xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.092

文献信息

• Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity
  作者：Jerome C. Bressi、Ron de Jong、Yiqin Wu、Andy J. Jennings、Jason W. Brown、Shawn O’Connell、Leslie W. Tari、Robert J. Skene、Phong Vu、Marc Navre、Xiaodong Cao、Anthony R. Gangloff

  DOI：10.1016/j.bmcl.2010.03.092

  日期：2010.5

  A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[ 3-( 1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC(50)s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21(waf). Compound 5x displays efficacy in human tumor xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of symmetrical 2,2′,4,4′-tetrasubstituted[4,4′-bioxazole]-5,5′(4<i>H</i>,4′<i>H</i>)-diones and their reactions with some nucleophiles
  作者：Kenneth K. Andersen、Daniel F. Gloster、Diana D. Bray、Massud Shoja、Anders Kjaer

  DOI：10.1002/jhet.5570350210

  日期：1998.3

  Several symmetrical 2,2′,4,4′-tetrasubstituted[4,4′-bioxazole]-5,5′(4H,4′H)-diones 1a-f were obtained by dehydrodimerization of 5(4H)-oxazolones 2a-f. The configurations of four were established; one by X-ray crystallography rac-1c, and three rac-1a, meso-1a and rac-1b by 1H nmr spectroscopy of their derivatives. Upon being heated, the bioxazolones isomerized, presumably by breakage of the 4,4′-carboncarbon

  几个对称2,2'，4,4'-四取代[4,4'- bioxazole] -5,5-'（4 ħ，4' ħ） -二酮1A-F 5（4 dehydrodimerization获得ħ） -恶唑酮2a-f。建立了四个的配置。1个通过X射线晶体学rac - 1c进行分析，三个rac - 1a，meso - 1a和rac - 1b通过1 H nmr光谱对其衍生物进行分析。加热后，生物恶唑酮被异构化，可能是由于4,4'-碳的断裂碳键形成自由基，然后重组。交叉实验的结果与该异构化反应的自由基性质一致。用甲醇和胺亲核试剂处理三种生物恶唑酮rac - 1a，meso - 1a和rac - 1c，可得到α，α'-脱氢二聚氨基酸的酯和酰胺衍生物7-11。