methyl 3-(4-bromophenyl)-4-nitrobutyrate | 540481-48-9

• 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: methyl 3-(4-bromophenyl)-4-nitrobutyrate
• 英文别名: Methyl 3-(4-bromophenyl)-4-nitrobutanoate
• CAS: 540481-48-9
• 化学式: C₁₁H₁₂BrNO₄
• 分子量: 302.125
• InChiKey: UZDIBTNDTOPDDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-bromophenyl)-4-nitrobutyrate 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以85%的产率得到4-(4-溴苯基)-2-吡咯烷酮
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a dansyled amino acid derivative as an imaging agent for apoptosis

  摘要：

  To develop a small molecule-based biomarker for in vivo apoptosis imaging, a dansyled amino acid derivative (BNSBA) was designed and synthesized in good yield. The biological evaluation demonstrated that BNSBA selectively binds to apoptotic cancer cells and is localized within the cytoplasm of cells that bound annexin V on the plasma membrane. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.091
• 作为产物：
  描述：

  methyl 4-bromocinnamate 、 硝基甲烷 在 苄基-三乙基-铵 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 以75%的产率得到methyl 3-(4-bromophenyl)-4-nitrobutyrate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a dansyled amino acid derivative as an imaging agent for apoptosis

  摘要：

  To develop a small molecule-based biomarker for in vivo apoptosis imaging, a dansyled amino acid derivative (BNSBA) was designed and synthesized in good yield. The biological evaluation demonstrated that BNSBA selectively binds to apoptotic cancer cells and is localized within the cytoplasm of cells that bound annexin V on the plasma membrane. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.091

文献信息

• Discovery and Structure−Activity Relationships of Novel Piperidine Inhibitors of Farnesyltransferase
  作者：Shinji Nara、Rieko Tanaka、Jun Eishima、Mitsunobu Hara、Yuichi Takahashi、Shizuo Otaki、Robert J. Foglesong、Philip F. Hughes、Shelley Turkington、Yutaka Kanda

  DOI：10.1021/jm020522k

  日期：2003.6.1

  A novel piperidine series of farnesyltransferase (FTase) inhibitors is described. Systematic medicinal chemistry studies starting with the lead compound, discovered from a 5-nitropiperidin-2-one combinatorial library, resulted in a potent series of novel FTase inhibitors. We found that all of four substituents of the piperidine core played an important role for FTase inhibition. A 10-fold increase

  描述了新颖的法尼基转移酶（FTase）抑制剂的哌啶系列。从5-硝基哌啶-2-酮组合文库中发现的先导化合物开始的系统药物化学研究，产生了一系列有效的新型FTase抑制剂。我们发现哌啶核的所有四个取代基均对FTase抑制起重要作用。通过将哌啶-2-一核心改变为相应的哌啶核心，观察到效力提高了10倍。发现这类化合物以Ras竞争性方式抑制法呢基转移酶。几种有效抑制剂的光学拆分结果表明，（+）-对映异构体显示出有效的法呢基转移酶抑制作用。（+）-8抑制FTase的IC（50）为1.9 nM。
• Design, synthesis, and biological evaluation of a dansyled amino acid derivative as an imaging agent for apoptosis
  作者：Wenbin Zeng、Weimin Miao、George Kabalka、Michael Le Puil、John Biggerstaff、David Townsend

  DOI：10.1016/j.tetlet.2008.08.091

  日期：2008.11

  To develop a small molecule-based biomarker for in vivo apoptosis imaging, a dansyled amino acid derivative (BNSBA) was designed and synthesized in good yield. The biological evaluation demonstrated that BNSBA selectively binds to apoptotic cancer cells and is localized within the cytoplasm of cells that bound annexin V on the plasma membrane. (C) 2008 Elsevier Ltd. All rights reserved.