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...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.展开更多
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 der...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 1^H NMR, 13^C 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 sp^2 hybridization configuration of the two nitrogen atoms of the quinoxalone ring.展开更多
Aryl diketo acid derivatives are one of the most promising HIV-1 integrase（IN） inhibitors. With a view to substitute the critical diketo acid pharmacophore with the diketo benzimidazole unit, the coupling reaction o...Aryl diketo acid derivatives are one of the most promising HIV-1 integrase（IN） inhibitors. With a view to substitute the critical diketo acid pharmacophore with the diketo benzimidazole unit, the coupling reaction of compound 4 with o-phenylenediamine was carried out. However, the reaction product, compound 5, was confirmed to be 3-{ [ 3- （phenylsulfonamido） benzoyl] methylidene t -3,4-dihydroquinoxaline-2 （1H） -one rather than the 2-benzimidazole derivative by using X-ray diffraction. Owing to its low solubility in water, the evaluation of the anti-HIV IN activity of the synthesized compound 5 could not be carried out. Consequently, the ion-binding properties of compound 5 in the absence of HIV-1 IN were investigated with UV-Vis spectroscopy in organic solvents. The results show that such a compound can selectively recognize Cu^2＋.展开更多
基金Project supported by the National Natural Science Foundation of China （No. 20402001）, the Special Foundation for Beijing Municipal （No. 2004D0501520 and Beijing Novel Project （No. 2005B 10）.
文摘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.
基金Project supported by the National Natural Science Foundation of China （No. 20402001）, Beijing Novel Project （No. 2005B10） and Beijing Natural Science Foundation （No. 2062003）.Acknowledgements We would like to thank Prof. He, L. N. and Miss Du, Y. in College of Chemistry, Nankai University for their help in measuring NMR for a part of the compounds.
文摘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 1^H NMR, 13^C 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 sp^2 hybridization configuration of the two nitrogen atoms of the quinoxalone ring.
基金Supported by the National Natural Science Foundation of China(No. 20402001)Special Foundation for Beijing Municipal In-telligent(No. 20041D0501520)Beijing Natural Science Foundation(No. 2062003).
文摘Aryl diketo acid derivatives are one of the most promising HIV-1 integrase（IN） inhibitors. With a view to substitute the critical diketo acid pharmacophore with the diketo benzimidazole unit, the coupling reaction of compound 4 with o-phenylenediamine was carried out. However, the reaction product, compound 5, was confirmed to be 3-{ [ 3- （phenylsulfonamido） benzoyl] methylidene t -3,4-dihydroquinoxaline-2 （1H） -one rather than the 2-benzimidazole derivative by using X-ray diffraction. Owing to its low solubility in water, the evaluation of the anti-HIV IN activity of the synthesized compound 5 could not be carried out. Consequently, the ion-binding properties of compound 5 in the absence of HIV-1 IN were investigated with UV-Vis spectroscopy in organic solvents. The results show that such a compound can selectively recognize Cu^2＋.
