首页> 外文期刊>The Journal of Organic Chemistry >Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production
【24h】

Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production

机译:作为文库生产中间体的映体纯3取代的哌嗪-2-乙酸酯的合成

获取原文
获取原文并翻译 | 示例
           

摘要

The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 - 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp(3)-enriched compound libraries for drug discovery, these diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as scaffolds for parallel library synthesis and as intermediates for the production of novel piperazine compounds.
机译:哌嗪杂环在FDA批准的药物和生物活性化合物中广泛地利用,但其化学多样性通常限于环氮取代,使四种碳原子未充分利用。使用高效的六步合成,将手性氨基酸转化为3-取代的哌嗪-2-乙酸酯,作为非对映异构混合物,其顺式和反式产品(分别0.56 - & 2.2:1分别)可以进行色谱分离。从五个氨基酸(两种抗脂肪糖)获得20个单丙约合的手性2,3-二取代哌嗪的完整基质,每个哌嗪,各为单个绝对体式器,除其中一中除其中。在保持更多CSP(3)的整体目的以防用于药物发现,这些不同和通用的哌嗪可以在氮原子上官能化,使它们用作平行文库合成的支架和作为中间体生产新型哌嗪化合物。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱:kefu@zhangqiaokeyan.com

京公网安备:11010802029741号 ICP备案号:京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有
  • 客服微信

  • 服务号