Design, Synthesis and Cu2+ Recognition of β-Diketoacid and Quinoxalone Derivatives Bearing Caffeoyl or Galloyl Moieties Linked by Arylamide as Potential HIV Integrase Inhibitors
✍ Scribed by Yi-Sheng Xu; Cheng-Chu Zeng; Xue-Mei Li; Ru-Gang Zhong; Yi Zeng
- Book ID
- 102098997
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 133 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0256-7660
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✦ Synopsis
An efficient procedure for the synthesis of caffeoyl-and galloyl-containing β-diketoacid derivatives linked by arylamide was reported by, in the key step, dissolving the corresponding phenyl methyl ketone in THF/DME in the presence of NaOMe as base and dimethyl oxalate as oxalylation reagent, and then separating the sodium ketoenolate ester. The resulting β-diketoacids underwent further condensation reaction with o-phenylenediamine to generate quinoxalone derivatives in good yield, rather than 2-benzimidazol. The preliminary ion binding properties of quinoxalone derivatives were also investigated. UV-Vis spectra showed that these compounds could selectively recognize Cu 2＋ ion in ethanol and form a 1∶2 complex.
Keywords
diketoacid, quinoxalone derivative, HIV integrase inhibitor, Cu 2＋ recognition Figure 1 Several typical polyhydroxylated aromatics and aryl diketoacid derivatives as HIV integrase inhibitors. β-Diketoacid and quinoxalone derivatives