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Design, Synthesis and Cu 2+ Recognition of β ‐Diketoacid and Quinoxalone Derivatives Bearing Caffeoyl or Galloyl Moieties Linked by Arylamide as Potential HIV Integrase Inhibitors
Author(s) -
Xu YiSheng,
Zeng ChengChu,
Li XueMei,
Zhong RuGang,
Zeng Yi
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690203
Subject(s) - chemistry , integrase , reagent , yield (engineering) , combinatorial chemistry , sodium , medicinal chemistry , organic chemistry , dna , biochemistry , materials science , metallurgy
Abstract 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.