A series of Bronsted acidic ionic liquids(ILs) were prepared and used for Biginelli-type condensation reaction among aromatic aldehydes, urea or thiourea and cyclopentanone. Through this reaction, the synthesis of v...A series of Bronsted acidic ionic liquids(ILs) were prepared and used for Biginelli-type condensation reaction among aromatic aldehydes, urea or thiourea and cyclopentanone. Through this reaction, the synthesis of various pyrimidinones could be achieved. Of interest, it was found that the reaction was efficiently catalyzed by a novel, eco-friendly functionalized IL [C3SO3HDoim]HSO4, which could be reused for at least 7 times without significantly loss of catalytic activity. The reaction proceeded efficiently at 80℃ to afford the desired products in good yield(up to 96%). In addition, a possible mechanism that accounted for the IL [C3SO3HDoim]HSO4-catalyzed reaction was proposed.展开更多
A class of new potential antibacterial agents with distinctive pyrimidinone benzimidazole skeleton was developed through nucleophilic substitution and Biginelli reaction starting from urea,ethyl 4-chloroacetoacetate a...A class of new potential antibacterial agents with distinctive pyrimidinone benzimidazole skeleton was developed through nucleophilic substitution and Biginelli reaction starting from urea,ethyl 4-chloroacetoacetate and various aldehydes.Some target molecules exhibited strong antibacterial activities,especially pyrimidinone benzimidazole hybrid 9e possessed the strongest inhibitory effects on the growth of E.faecalis and P.aeruginosa with a lower MIC value of 1μg/mL than norfloxacin.Moreover,compound 9e displayed strong antibiofilm capacity,low drug resistance and excellent biosafety toward human red blood cells.Further research revealed that compound 9e could disrupt membrane integrity and cause leakage of cellular components such as proteins and nucleic acids.Meanwhile,compound 9e could decrease lactate dehydrogenase activity,block cell metabolism and interact with DNA in an intercalation manner.展开更多
We describe here a rapid process for the preparation of new 9-chloromethyl-12-aryl-10,12-dihydrobenzo[5,6]chromeno[2,3-d]pyrimidin-11-ones 5a-d and 10-chloromethyl-7-aryl-7,9-dihydrobenzo[7,8]chromeno[2,3-d]pyrimidin-...We describe here a rapid process for the preparation of new 9-chloromethyl-12-aryl-10,12-dihydrobenzo[5,6]chromeno[2,3-d]pyrimidin-11-ones 5a-d and 10-chloromethyl-7-aryl-7,9-dihydrobenzo[7,8]chromeno[2,3-d]pyrimidin-8-ones 6a-d by two different methods utilizing microwave irradiation. This methodology provides better yields(72%–80%) and high purity of the title compounds.展开更多
This paper describes a very simple, efficient synthesis of quinazolinones and chromeno[d]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds(dimedone/4-hydroxycoumarin) us...This paper describes a very simple, efficient synthesis of quinazolinones and chromeno[d]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds(dimedone/4-hydroxycoumarin) using nano-sized CuI particles under solvent-free conditions. The highlights of this new method are based on using an effective and recyclable catalyst, affording high yields of products,mild reaction conditions, facile work-up and purification.展开更多
An efficient method for the preparation of thieno[3',2':2,3]pyrido[4,5-d]thiazolo[3,2-a] pyrimidin-5-ones 5 is described. The key intermediate, 7-(3-amino-4-cyano-5-phenyl aminothieno-2-yl)-5H-thiazolo-[80_TD$IF]...An efficient method for the preparation of thieno[3',2':2,3]pyrido[4,5-d]thiazolo[3,2-a] pyrimidin-5-ones 5 is described. The key intermediate, 7-(3-amino-4-cyano-5-phenyl aminothieno-2-yl)-5H-thiazolo-[80_TD$IF]3,2-a]pyrimidin-5-one(3), was synthesized from 7-chloromethyl-5H-thiazolo[3,2-a]pyrimidin-5-one(1)with potassium-(2,2-dicyano-1-phenylaminoethen-1-yl)thiolate(2) by Thorpe–Ziegler isomerization.Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet–Spengler reaction provided thieno-pyridine fused thiazolo[3,2-a]pyrimidines under p-Ts OH as catalyst in good yields.展开更多
3,3-(1,4-Phenylene)-bis(polysubstituted furo[3,2-d]pyrimidin-4(3 H)-ones 3 were synthesized from the starting material of functionalized iminophosphorane 1 by aza-Wittig reaction. All of the title compounds were chara...3,3-(1,4-Phenylene)-bis(polysubstituted furo[3,2-d]pyrimidin-4(3 H)-ones 3 were synthesized from the starting material of functionalized iminophosphorane 1 by aza-Wittig reaction. All of the title compounds were characterized by 1H NMR, MS and elemental analysis. Meanwhile, the single crystal of compound 3 c, C46H68N6O10, was also obtained and determined by X-ray crystallography. Crystal data: triclinic, space group P1, a = 9.0017(3), b = 10.5908(4), c = 14.0116(5) A, α = 108.582(2)°, β = 94.296(1)°, γ = 105.059(2)°, V = 1204.40(7) ?3, Z = 1, F(000) = 466, Dc = 1.193 g/cm3, μ = 0.084 mm-1, R = 0.0998 and wR = 0.2146 for 4213 independent reflections(Rint = 0.0689) and 2796 observed ones(I > 2σ(I)). The in vitro antitumor activities of compounds 3 a^3 c were preliminarily evaluated by the standard MTT assay.展开更多
Two new thieno[2,3-d]pyrimidin-4(3H)-one derivatives,C24H22 Cl N3O2S(5a) and C25H25N3O2S(5b),have been synthesized via a tandem aza-Wittig reaction.This tandem reaction has many attractive aspects such as easily...Two new thieno[2,3-d]pyrimidin-4(3H)-one derivatives,C24H22 Cl N3O2S(5a) and C25H25N3O2S(5b),have been synthesized via a tandem aza-Wittig reaction.This tandem reaction has many attractive aspects such as easily accessible and versatile starting materials,mild conditions and high yields.Both compounds have been characterized by elemental analysis,HR-MS,IR,NMR spectra and X-ray single-crystal diffraction.Compound 5a crystallizes in monoclinic,space group P21/c with a = 9.986(3),b = 14.263(4),c = 15.530(5)A,β = 93.806(5)o,V = 2207.1(11) A^3,Mr = 451.96,Z = 4,Dc = 1.360 g/cm3,F(000) = 944,μ = 0.294 mm-1,Mo Kα radiation(λ = 0.71073 A),the final R = 0.0444 and w R = 0.1219 for 3407 observed reflections with I 〉 2σ(I).Compound 5bcrystallizes in triclinic,space group P1 with a = 8.974(4),b = 10.766(5),c = 12.260(6) A,β = 93.047(7)o,V = 1122.1(9) A^3,Mr = 431.54,Z = 2,Dc = 1.277 g/cm3,F(000) = 456,μ = 0.170 mm-1,Mo Kα radiation(λ = 0.71073 A),the final R = 0.0378 and w R = 0.1072 for 3806 observed reflections with I 〉 2σ(I).The preliminary antibacterial activities of 5a and 5b were investigated.Compound 5a showed 71.3% and 79.2% in vitro inhibition against Fusarium oxysporium and Rhizoctonia solani,respectively.Compound 5b showed 75.3% in vitro inhibition against Rhizoctonia solani.展开更多
The dense networks of conventional hydrogel hinder the efficient cell penetration and thus tissue regeneration.In this study,a macroporous cryogel with excellent mechanical properties was designed and fabricated throu...The dense networks of conventional hydrogel hinder the efficient cell penetration and thus tissue regeneration.In this study,a macroporous cryogel with excellent mechanical properties was designed and fabricated through cryogelation and crosslinking of methacrylated gelatin(Gel-MA)and gelatin grafted with 2-ureido-4[1H]-6-methyl-pyrimidinone(Gel-UPY).The successful modification of the two functional units on the side chain of gelatin was confirmed by ^(1)H-NMR and infrared spectroscopy.The macroporous structure of cryogel was verified by scanning electron microscopy and confocal microscopy.The compressive modulus of cryogel(110 kPa)was 2 magnitudes higher than that of the conventional hydrogel of the same chemical compositions(8 kPa).Both the hydrogel and cryogel exhibited excellent stress-recovery ability.The cryogel could well maintain the viability of chondrocytes and facilitated their migration into the scaffold interior.After being implanted into osteochondral defects in rabbits for 12 w,the Gel-MA/Gel-UPY cryogel better facilitated the regeneration of upper cartilage and subchondral bone compared to the conventional hydrogel.展开更多
A green,efficient and convenient N-heterocyclic carbene-catalyzed procedure for the synthesis of novel 2,3-dihydroquinazolin-4(1H)-one derivates via condensation of o-aminonitriles and various carbonyl compounds was d...A green,efficient and convenient N-heterocyclic carbene-catalyzed procedure for the synthesis of novel 2,3-dihydroquinazolin-4(1H)-one derivates via condensation of o-aminonitriles and various carbonyl compounds was described.展开更多
文摘A series of Bronsted acidic ionic liquids(ILs) were prepared and used for Biginelli-type condensation reaction among aromatic aldehydes, urea or thiourea and cyclopentanone. Through this reaction, the synthesis of various pyrimidinones could be achieved. Of interest, it was found that the reaction was efficiently catalyzed by a novel, eco-friendly functionalized IL [C3SO3HDoim]HSO4, which could be reused for at least 7 times without significantly loss of catalytic activity. The reaction proceeded efficiently at 80℃ to afford the desired products in good yield(up to 96%). In addition, a possible mechanism that accounted for the IL [C3SO3HDoim]HSO4-catalyzed reaction was proposed.
基金supported by grants from the National Natural Science Foundation of China(No.21971212)the Research Fellowship for International Young Scientists from International(Regional)-Cooperation and Exchange Program of China National Natural ScienceFoundation(No.81350110523)theKey Project of Innovation Research 2035Pilot Plan of Southwest University(SWU-XDZD22007).
文摘A class of new potential antibacterial agents with distinctive pyrimidinone benzimidazole skeleton was developed through nucleophilic substitution and Biginelli reaction starting from urea,ethyl 4-chloroacetoacetate and various aldehydes.Some target molecules exhibited strong antibacterial activities,especially pyrimidinone benzimidazole hybrid 9e possessed the strongest inhibitory effects on the growth of E.faecalis and P.aeruginosa with a lower MIC value of 1μg/mL than norfloxacin.Moreover,compound 9e displayed strong antibiofilm capacity,low drug resistance and excellent biosafety toward human red blood cells.Further research revealed that compound 9e could disrupt membrane integrity and cause leakage of cellular components such as proteins and nucleic acids.Meanwhile,compound 9e could decrease lactate dehydrogenase activity,block cell metabolism and interact with DNA in an intercalation manner.
基金the Ministry of Higher Education, Scientific Research and Technology of Tunisia and the University of Toulouse III for financial support
文摘We describe here a rapid process for the preparation of new 9-chloromethyl-12-aryl-10,12-dihydrobenzo[5,6]chromeno[2,3-d]pyrimidin-11-ones 5a-d and 10-chloromethyl-7-aryl-7,9-dihydrobenzo[7,8]chromeno[2,3-d]pyrimidin-8-ones 6a-d by two different methods utilizing microwave irradiation. This methodology provides better yields(72%–80%) and high purity of the title compounds.
基金the financial support from the Research Council of East Tehran Branch, Islamic Azad University
文摘This paper describes a very simple, efficient synthesis of quinazolinones and chromeno[d]pyrimidinones from the reaction of aryl aldehydes, urea/thiourea and active methylene compounds(dimedone/4-hydroxycoumarin) using nano-sized CuI particles under solvent-free conditions. The highlights of this new method are based on using an effective and recyclable catalyst, affording high yields of products,mild reaction conditions, facile work-up and purification.
基金partially supported by innovation team project of Liaoning Province Education Department(No.2015001)
文摘An efficient method for the preparation of thieno[3',2':2,3]pyrido[4,5-d]thiazolo[3,2-a] pyrimidin-5-ones 5 is described. The key intermediate, 7-(3-amino-4-cyano-5-phenyl aminothieno-2-yl)-5H-thiazolo-[80_TD$IF]3,2-a]pyrimidin-5-one(3), was synthesized from 7-chloromethyl-5H-thiazolo[3,2-a]pyrimidin-5-one(1)with potassium-(2,2-dicyano-1-phenylaminoethen-1-yl)thiolate(2) by Thorpe–Ziegler isomerization.Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet–Spengler reaction provided thieno-pyridine fused thiazolo[3,2-a]pyrimidines under p-Ts OH as catalyst in good yields.
基金supported by the fund of Hubei Cooperative Innovation Center(No.2011JH-2014CXTT07)the Key Project of Project of Hubei University of Medicine(No.2014CXZ-05)
文摘3,3-(1,4-Phenylene)-bis(polysubstituted furo[3,2-d]pyrimidin-4(3 H)-ones 3 were synthesized from the starting material of functionalized iminophosphorane 1 by aza-Wittig reaction. All of the title compounds were characterized by 1H NMR, MS and elemental analysis. Meanwhile, the single crystal of compound 3 c, C46H68N6O10, was also obtained and determined by X-ray crystallography. Crystal data: triclinic, space group P1, a = 9.0017(3), b = 10.5908(4), c = 14.0116(5) A, α = 108.582(2)°, β = 94.296(1)°, γ = 105.059(2)°, V = 1204.40(7) ?3, Z = 1, F(000) = 466, Dc = 1.193 g/cm3, μ = 0.084 mm-1, R = 0.0998 and wR = 0.2146 for 4213 independent reflections(Rint = 0.0689) and 2796 observed ones(I > 2σ(I)). The in vitro antitumor activities of compounds 3 a^3 c were preliminarily evaluated by the standard MTT assay.
基金Supported by the National Natural Science Foundation of China(No.21102084)Natural Science Foundation(No.KJ2010B001)Scientific Research Innovation Foundation of Graduate School of China Three Gorges University(No.2011CX052)
文摘Two new thieno[2,3-d]pyrimidin-4(3H)-one derivatives,C24H22 Cl N3O2S(5a) and C25H25N3O2S(5b),have been synthesized via a tandem aza-Wittig reaction.This tandem reaction has many attractive aspects such as easily accessible and versatile starting materials,mild conditions and high yields.Both compounds have been characterized by elemental analysis,HR-MS,IR,NMR spectra and X-ray single-crystal diffraction.Compound 5a crystallizes in monoclinic,space group P21/c with a = 9.986(3),b = 14.263(4),c = 15.530(5)A,β = 93.806(5)o,V = 2207.1(11) A^3,Mr = 451.96,Z = 4,Dc = 1.360 g/cm3,F(000) = 944,μ = 0.294 mm-1,Mo Kα radiation(λ = 0.71073 A),the final R = 0.0444 and w R = 0.1219 for 3407 observed reflections with I 〉 2σ(I).Compound 5bcrystallizes in triclinic,space group P1 with a = 8.974(4),b = 10.766(5),c = 12.260(6) A,β = 93.047(7)o,V = 1122.1(9) A^3,Mr = 431.54,Z = 2,Dc = 1.277 g/cm3,F(000) = 456,μ = 0.170 mm-1,Mo Kα radiation(λ = 0.71073 A),the final R = 0.0378 and w R = 0.1072 for 3806 observed reflections with I 〉 2σ(I).The preliminary antibacterial activities of 5a and 5b were investigated.Compound 5a showed 71.3% and 79.2% in vitro inhibition against Fusarium oxysporium and Rhizoctonia solani,respectively.Compound 5b showed 75.3% in vitro inhibition against Rhizoctonia solani.
基金the Key research and development program of Zhejiang Province(No.2021C03113)the Natural Science Foundation of Zhejiang Province(No.LD21E030001).
文摘The dense networks of conventional hydrogel hinder the efficient cell penetration and thus tissue regeneration.In this study,a macroporous cryogel with excellent mechanical properties was designed and fabricated through cryogelation and crosslinking of methacrylated gelatin(Gel-MA)and gelatin grafted with 2-ureido-4[1H]-6-methyl-pyrimidinone(Gel-UPY).The successful modification of the two functional units on the side chain of gelatin was confirmed by ^(1)H-NMR and infrared spectroscopy.The macroporous structure of cryogel was verified by scanning electron microscopy and confocal microscopy.The compressive modulus of cryogel(110 kPa)was 2 magnitudes higher than that of the conventional hydrogel of the same chemical compositions(8 kPa).Both the hydrogel and cryogel exhibited excellent stress-recovery ability.The cryogel could well maintain the viability of chondrocytes and facilitated their migration into the scaffold interior.After being implanted into osteochondral defects in rabbits for 12 w,the Gel-MA/Gel-UPY cryogel better facilitated the regeneration of upper cartilage and subchondral bone compared to the conventional hydrogel.
基金Financial support from the International S&T Cooperation Program of China(No.2012DFR40240)is gratefully acknowledged.
文摘A green,efficient and convenient N-heterocyclic carbene-catalyzed procedure for the synthesis of novel 2,3-dihydroquinazolin-4(1H)-one derivates via condensation of o-aminonitriles and various carbonyl compounds was described.