Topomer CoMFA models have been used to optimize the potency of 15 biologically active acridone derivatives se- lected from the literature. Their 3D chemical structures were sliced into three acyclic R groups, to produ...Topomer CoMFA models have been used to optimize the potency of 15 biologically active acridone derivatives se- lected from the literature. Their 3D chemical structures were sliced into three acyclic R groups, to produce a fragment that is present in each training set. The analysis was successful with 3 as the number of components that provided the highest q2 results: q2 is 0.56, which is the cross-validated coefficient for the specified number of components, giving rise to 0.37 standard error of estimate (q2 stderr), and a conventional coefficient (r2) of 0.82, whose standard error of estimate is 0.24. These results provide structure-activity relationship (sar) among the compounds. The result of the To-pomer CoMFA studies was used to design novel derivatives for future studies.展开更多
Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide(DMSO)under air atmosphere and additive-fr...Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide(DMSO)under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields.This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C-N bond,CO extrusion,Cu migration,reductive elimination and DMSO-aided proton migration processes,involving multiple types of bond cleavage and formation in a single chemical step.展开更多
6,7-Methylenedioxy-3-thia-1(2H,4H)acridone and the related acridine-fused quinolines and pyridines,and also their flavylium-perchlorates were synthesized.The structures of all these compounds prepared are characterize...6,7-Methylenedioxy-3-thia-1(2H,4H)acridone and the related acridine-fused quinolines and pyridines,and also their flavylium-perchlorates were synthesized.The structures of all these compounds prepared are characterized by elemental analysis.IR and H-NMR spectra.展开更多
Twenty 10-hydrocarbylacridones and 2-methylacridone, 1-hydroxyacridone were synthesized from acridone and characterized by mp, IR, UV, 1H NMR and MS. Using Nd:YAG as a laser source, the second-order harmonic generatio...Twenty 10-hydrocarbylacridones and 2-methylacridone, 1-hydroxyacridone were synthesized from acridone and characterized by mp, IR, UV, 1H NMR and MS. Using Nd:YAG as a laser source, the second-order harmonic generation (SHG) values of the acridone derivatives were measured in powder state as compared with urea powder. The results showed that the SHG values of some of 10-hydrocarbylacridones were higher than that of urea, while others were lower. Although the hydrocarbyl substituents (R) attached to nitrogen atom of acridone were different in size and electronegativity, they had a little effect on the SHG values of 10-hydrocarbylacridones. Substituents, such as methyl or hydroxy group connected to the phenyl ring, caused a little effect on the SHG values, too, compared with acrid one. The ability of R to push electron toward the nitrogen atom or to pull electron from the nitrogen atom play an important role on the maximum wavelengths of UV-visible absorption of acridone derivatives.展开更多
A series of 10-substituted 9-aryl-3,4,6,7,9,10-hexahydroacridine-1,8（2H,5H）-dione derivatives 2 were synthesized by a two-step reaction.All the compounds were characterized by IR,MS,and ^1H NMR.Crystals of 1a and 2c...A series of 10-substituted 9-aryl-3,4,6,7,9,10-hexahydroacridine-1,8（2H,5H）-dione derivatives 2 were synthesized by a two-step reaction.All the compounds were characterized by IR,MS,and ^1H NMR.Crystals of 1a and 2c were obtained and determined by X-ray single-crystal diffraction.Crystal data of 1a：C_（20）H_（22）O_5,orthorhombic system,space group Pbcn,a = 15.8888（19）,b = 18.228（2）,c = 11.6926（13） A,V = 3386.4（7） A^3,Z = 8,F（000） = 1456,Dc = 1.343 g/cm^3,R = 0.0456 and w R = 0.1600.Crystal data of 2c：C_（26）H_（24） Cl NO_3,monoclinic system,space group P2_1/n,a = 8.628（2）,b = 10.912（3）,c = 22.425（7） A,β = 90.786（4）°,V = 2111.1（10） A^3,Z = 4,F（000） = 912,D_c = 1.365 g/cm^3,R = 0.0613,and w R = 0.1196.The results of biological experiments show that compounds 2b and 2c could inhibit the proliferation of Hep G2 cells.展开更多
文摘Topomer CoMFA models have been used to optimize the potency of 15 biologically active acridone derivatives se- lected from the literature. Their 3D chemical structures were sliced into three acyclic R groups, to produce a fragment that is present in each training set. The analysis was successful with 3 as the number of components that provided the highest q2 results: q2 is 0.56, which is the cross-validated coefficient for the specified number of components, giving rise to 0.37 standard error of estimate (q2 stderr), and a conventional coefficient (r2) of 0.82, whose standard error of estimate is 0.24. These results provide structure-activity relationship (sar) among the compounds. The result of the To-pomer CoMFA studies was used to design novel derivatives for future studies.
基金National Natural Science Foundation of China(Nos.U1604285 and 21877206)the Program for Changjiang Scholars and Innovative Research Team in University of China(No.IRT1061)the 111 Project(No.D17007)。
文摘Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide(DMSO)under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields.This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C-N bond,CO extrusion,Cu migration,reductive elimination and DMSO-aided proton migration processes,involving multiple types of bond cleavage and formation in a single chemical step.
文摘6,7-Methylenedioxy-3-thia-1(2H,4H)acridone and the related acridine-fused quinolines and pyridines,and also their flavylium-perchlorates were synthesized.The structures of all these compounds prepared are characterized by elemental analysis.IR and H-NMR spectra.
基金Project supported by the SeientificTechnical Commission of Guangzhou (No. 98-J-013-01)the National Natural Science Foundation for Doctors of Guangdong Province.
文摘Twenty 10-hydrocarbylacridones and 2-methylacridone, 1-hydroxyacridone were synthesized from acridone and characterized by mp, IR, UV, 1H NMR and MS. Using Nd:YAG as a laser source, the second-order harmonic generation (SHG) values of the acridone derivatives were measured in powder state as compared with urea powder. The results showed that the SHG values of some of 10-hydrocarbylacridones were higher than that of urea, while others were lower. Although the hydrocarbyl substituents (R) attached to nitrogen atom of acridone were different in size and electronegativity, they had a little effect on the SHG values of 10-hydrocarbylacridones. Substituents, such as methyl or hydroxy group connected to the phenyl ring, caused a little effect on the SHG values, too, compared with acrid one. The ability of R to push electron toward the nitrogen atom or to pull electron from the nitrogen atom play an important role on the maximum wavelengths of UV-visible absorption of acridone derivatives.
基金supported by National Natural Science Foundation of China for Young Scholars(No.21201087)Natural Science Foundation of Jiangsu Province(No.BK20131244&BK2012699)+1 种基金Jiangsu Overseas Research&Training Program for University Prominent Young&Middle-aged Teachers and Presidentsa start-up grant from Jiangsu University of Science and Technology of China
文摘A series of 10-substituted 9-aryl-3,4,6,7,9,10-hexahydroacridine-1,8（2H,5H）-dione derivatives 2 were synthesized by a two-step reaction.All the compounds were characterized by IR,MS,and ^1H NMR.Crystals of 1a and 2c were obtained and determined by X-ray single-crystal diffraction.Crystal data of 1a：C_（20）H_（22）O_5,orthorhombic system,space group Pbcn,a = 15.8888（19）,b = 18.228（2）,c = 11.6926（13） A,V = 3386.4（7） A^3,Z = 8,F（000） = 1456,Dc = 1.343 g/cm^3,R = 0.0456 and w R = 0.1600.Crystal data of 2c：C_（26）H_（24） Cl NO_3,monoclinic system,space group P2_1/n,a = 8.628（2）,b = 10.912（3）,c = 22.425（7） A,β = 90.786（4）°,V = 2111.1（10） A^3,Z = 4,F（000） = 912,D_c = 1.365 g/cm^3,R = 0.0613,and w R = 0.1196.The results of biological experiments show that compounds 2b and 2c could inhibit the proliferation of Hep G2 cells.
