Design and Synthesis of p/m-[p-(un)Substituted Phenylsulfonamido]phenyl β-Diketo Acids and Quinoxalone Derivatives

• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2007,（8）
• 页码范围: 1174-1182
• 页数: 9页
• 语种: 英文

摘要

Diketo acid derivatives are potent and selective HIV-1 integrase inhibitors. To investigate the detailed synthesis of those derivatives, a series of p/m-[p-(un)substituted phenylsulfonamido]phenyl β-diketo acid derivatives have been designed and synthesized. The quinoxalone derivatives as the potential bioisosteres of the biologically labile β-diketoacid pharmacophores have also been synthesized from reactions of the corresponding diketo acids with o-phenylenediamine. The structures of all diketo acid (ester) and quinoxalone derivatives were confirmed by 1H NMR, 13C NMR, IR, HRMS and/or MS (ESI). X-ray crystallographic analysis of 11b demonstrates a similar arrangement of the side chain of quinoxalone derivatives with the parent diketoacids due to the intramolecular hydrogen bond (O…H-N) and the sp2 hybridization configuration of the two nitrogen atoms of the quinoxalone ring.