Pyrido2,3 dpyrimidine carboxylate derivatives were synthesized through nucleophilic substitution reactions with the use of amidines, followed by 4haloanilines and malonic acid. Pdf synthesis of imidazo1,2apyridines and pyrido1,2. The biosynthetic pathway for the formation ump is shown. Synthesis and pharmacological screening of pyridopyrimidines as. Onepot synthesis of pyrido 2,3d pyrimidine derivatives using sulfonic acid functionalized sba15 and the study on their antimicrobial activities. A rapid onepot synthesis of pyrido2,3dpyrimidine derivatives. Efficient onepot synthesis of pyrano2,3dpyrimidinone. A series of 6bromo32morpholino methyl amino6substituted. Pyrido1,2 apyrimidines mol id structure formula chemical name mw id number cas number 10 ch11cl2n3o4s 2methoxycarbonyl methylthio7methyl4dichloromethylene3. The present invention relates to a novel pyrido2,3 dpyrimidine derivative having the formula 1.
Onepot synthesis of new pyrido 2,3d pyrimidine derivatives under. The nonnatural pyrido2,3dpyrimidine nucleoside f, which pairs preferentially with guanine g and adenine a within doublehelical dna, recognizes with high selectivity at base pairs within triplehelical complexes. Synthesis of pyrido1,2alpha symbol pyrimidine scaffolds. A series of pyrido2,3dpyrimidines derivatives have been prepared by onepot threecomponent reaction of 46aminouracil, malononitrile and aromatic aldehydes. Using the optimized reaction conditions for the synthesis of pyrido 2,3d pyrimidine and pyrano 2,3d pyrimidine derivatives, various aromatic aldehydes, were used table 5, table 6. Jun 01, 2015 a novel series of bicyclic pyrido 2,3dpyrimidines that contain an n 6substituted phenyl pyrido 2,3d pyrimidine 2,4,6triamine scaffold in which the substituted aniline is directly attached to the 6position of the pyrido 2,3d pyrimidine ring have been shown to be selective and potent inhibitors of pathogenic sources of dihydrofolate. The first reaction is the conjugation of carbamoyl phosphate and aspartate to make n.
Pyrazole based pyrido 2,3d pyrimidine diones are interesting compounds from both chemical and biological point of views, thus attracted the attention of several research groups. Pdf because of its potent and significant pharmacological activities, the 2amino4,6bis4chlorophenyl nicotinonitrile 1 used as a starting. Results are shown our catalyst had good catalytic activity short reaction time and high yield for all of aldehydes and different derivatives did not sufficient effect on the time and yield of products. Looking for online definition of pyrido pyrimidine 2pyridones in the medical dictionary. An efficient synthesis of pyrido2,3dpyrimidine derivatives. An efficient onepot threecomponent synthesis of pyrido2. We are interested in green synthesis2528 and heterocyclic chemistry. Pyrimidine biosynthesis unlike in purine biosynthesis, the pyrimidine ring is synthesized before it is conjugated to prpp. Synthesis and antitumor activity of new pyrido2,3 d. The styryl derivatives of pyrimidines and pyrido 1,2 pyrimidine are heterocyclic isosters of stilbenes, possesses different types of biological activity, and are also in the focus of research on obtaining new materials with opticalabsorption, emission, luminescent and other properties 4.
This efficient synthesis was done under microwave irradiation conditions method a and also using catalytic amount of diammonium hydrogen phosphate nh42hpo4 dahp in aqueous media method b. Synthesis and cytotoxicity evaluation of novel pyrido 3, 4d. Tu s, zhang j, zhu x, xu j, zhang y, wang q, jia r, jiang b, zhang j 2006 new potential inhibitors of cyclin dependent kinase 4. The results of the crystal structure determination of human dihydrofolate reductase hdhfr as a binary complex with the potent n9c10 reversedbridge antifolate inhibitor 2,4diamino6n3,4,5trimethoxybenzylnmethylaminopyrido2,3dpyrimidine 1 are reported for two independent polymorphic rhombohedral r3 lattices r31 and r32. The matrix photolyses of 3phenyl, 3pyridyl, and 3,4diphenylsydnones 16, 19, and 22 were investigated by matrixisolation infrared spectroscopy. Synthesis of pyrido1,2alpha symbol pyrimidine scaffolds and their dnabinding studies. An efficient and mild condensation reaction of 6aminouracil derivatives with various aromatic aldehydes and ethyl or methyl acetoacetate was performed in the presence of catalytic amounts of h14nap5w30o110sio2 as a recyclable, ecofriendly and green nanocatalyst to afford the desired pyrido2,3dpyrimidine derivatives in good to excellent yields. A series of novel pyrido 2,3dpyrimidine was efficiently synthesized in higher yield and it was subjected to antibacterial and antifungal activity. Fourteen different 6amino,4substituted phenyl2oxo4substituted. Pyridopyrimidines are of importance because of their close structural sim. Particularly contemplated compounds also include prodrug forms of the purine nucleoside analogs, and both purine nucleoside analogs and the corresponding prodrugs are employed in the reduction. When treated with copperii acetate, the pyrido 1,2apyrimidines. An efficient onepot threecomponent synthesis of pyrido2,3.
Synthesis and biological evaluation of pyrido 2, 3d pyrimidine carboxylate derivatives. In the case of the 5,6,7,8tetrahydro compounds of formula ib, the carbon atom in the 6position of the pyrido2,3dpyrimidine ring system also is a chiral center, leading to d,l and 1,ldiastereoisomers if r 3 is hydrogen and to d,1,l, d,d,l, 1,1,l, and 1,d,ldiastereoisomers if r 3 is other than hydrogen. Meaning of pyrido pyrimidine 2pyridones medical term. The ir spectrum of 17 showed bands due to nh 2 and nh functionalities in the region 33403150 cm. The pdf file you selected should load here if your web browser has a pdf reader. A homology model of eef2k was created, and compound 6 a484954, abbott laboratories was docked in thecatalytic domain of eef2k. Evaluation of pyridopyrimidine derivatives ixii as cgmp and camp. Electronic supplementary information an efficient route for the synthesis of a new class of pyrido2,3 dpyrimidine derivatives shujiang tu, junyong zhang, runhong jia, bo jiang, yan zhang, hong jiang. Pyridopyrimidine and its derivatives have been studied due to a variety of chemical and biological significance. A series of novel spiro derivatives containing pyrido1,2. Pyrimidine 1,3dioxides require high activation for direct formation. Jul 11, 1994 the nonnatural pyrido 2,3d pyrimidine nucleoside f, which pairs preferentially with guanine g and adenine a within doublehelical dna, recognizes with high selectivity at base pairs within triplehelical complexes.
A purine nucleoside analog includes a pyrido2,3dpyrimidine or a pyrimido4,5dpyrimidine and further has a sugar moiety that is optionally modified at the c2. Meaning of pyridopyrimidine 2pyridones medical term. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Pdf an efficient synthesis of pyrido2,3dpyrimidine derivatives. All structured data from the file and property namespaces is available under the creative commons cc0 license. The pdf file you selected should load here if your web browser has a pdf reader plugin installed for example, a recent version of adobe acrobat reader. This protocol has the advantages of good yields, broad substrate scope and simple work. Each step in the pathway is shown indicating the substrates used and the products formed. The sar studies identified compound 8h 8chloron2isopropyln4phenethylquinazoline2,4diamine as a potent inhibitor of a.
Compound 2 was used as the key intermediate to prepare the pyrazolopyrido pyrimidine derivatives through its reaction with formic acid, formamideformic acid. Synthesis of pyrido1,2alpha symbol pyrimidine scaffolds and their dnabinding studies habarakada liyanage, thakshila udayakanthi liyanage advisor. Design, synthesis, and molecular modeling of novel pyrido2,3. Pdf acute secretory diarrhea induced by infection with enterotoxigenic strains of escherichia coli involves binding of stable toxin sta to its. Pyrimidines and methylpyrimidines are susceptible to decomposition, ringcarbon oxidation, and ringopening reactions on direct noxidation, resulting in low yields of noxides. Some features of this site may not work without it. Synthesis of some pyrido 2,3d pyrimidine ring system synthesis of pyrido 2,3d pyrimidine derivatives was performed according to the following general strategies. This efficient synthesis was done under microwave irradiation conditions method a and also using catalytic amount of diammonium hydrogen phosphate nh 4 2 hpo 4 dahp in aqueous media method b. Pdf synthesis and biological evaluation of pyrido 2, 3. Synthesis and biological evaluation of pyrido 2, 3d. The importance of pyridopyrimidines as biologically ac tive compounds includes their use as antibacterial.
An external file that holds a picture, illustration, etc. Design and synthesis of new pyrido 2, 3d pyrimidine1, 4dione. Structure, properties, spectra, suppliers and links for. Pyrido4,3 dpyrimidine c7h5n3 cid 19883218 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. A novel series of bicyclic pyrido2,3dpyrimidines that contain an n 6substituted phenylpyrido2,3dpyrimidine2,4,6triamine scaffold in which the substituted aniline is directly attached to the 6position of the pyrido2,3dpyrimidine ring have been shown to be selective and potent inhibitors of pathogenic sources of dihydrofolate. Unless otherwise noted, the contents of the fda website. Pdf a series of pyrido2,3dpyrimidine derivatives were designed and synthesized based on known cc chemokine receptor 4 ccr4 antagonists. Pdf structures of 4iminopyrido1,2apyrimidines, pyrido1. Files are available under licenses specified on their description page.
An efficient synthesis of pyrido2,3dpyrimidine derivatives via one. Pyrazole based pyrido2,3dpyrimidinediones are interesting compounds from both chemical and biological point of views, thus attracted the attention of several research groups. An efficient, simple, and catalystfree synthesis of spiroindeno1,2bpyrido2,3dpyrimidine5,3. Changing from the quinolone 1 to the analogous pyrido2,3dpyrimidine 2 improved the potency against dyrk1b to 0. Molecular diversity of fourcomponent synthesis of pyrazole. These novel derivatives have been screened for anticncer activity. A series of pyrido 2,3dpyrimidines derivatives have been prepared by onepot threecomponent reaction of 46aminouracil, malononitrile and aromatic aldehydes. Rearrange individual pages or entire files in the desired order. Synthesis of substituted pyrido1,2 a pyrimidines from 2. An efficient and mild condensation reaction of 6aminouracil derivatives with various aromatic aldehydes and ethyl or methyl acetoacetate was performed in the presence of catalytic amounts of h14nap5w30o110sio2 as a recyclable, ecofriendly and green nanocatalyst to afford the desired pyrido 2,3d pyrimidine derivatives in good to excellent yields. A novel and efficient method for the synthesis of 6aminopyrimidine 21hthiones derivatives, pyrido 2,3d pyrimidine2 1hthiones derivatives and their glycosides. A quinazoline and pyrido3,2dpyrimidine based compound library was designed, synthesized and evaluated as multitargeting agents aimed at alzheimers disease ad.
Rapid discovery of pyrido3,4dpyrimidine inhibitors of. An efficient, simple, and catalystfree synthesis of spiroindeno1,2b pyrido 2,3d pyrimidine 5,3. Nitrogen containing heterocyclic ring such as pyrimidine is a promising structural moiety for drug designing. Journal of chemical and pharmaceutical research, 2016, 83. Synthesis of some pyrido2,3dpyrimidine ring system synthesis of pyrido2,3dpyrimidine derivatives was performed according to the following general strategies. Application of quinazoline and pyrido3,2dpyrimidine. Pdf a series of pyrido2,3dpyrimidines derivatives have been prepared by one pot threecomponent reaction of 46aminouracil, malononitrile and. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from fda. Aug 04, 1987 in the case of the 5,6,7,8tetrahydro compounds of formula ib, the carbon atom in the 6position of the pyrido 2,3d pyrimidine ring system also is a chiral center, leading to d,l and 1,ldiastereoisomers if r 3 is hydrogen and to d,1,l, d,d,l, 1,1,l, and 1,d,ldiastereoisomers if r 3 is other than hydrogen. Synthesis reactions and biological activity of functionalized pyrido. A novel and efficient method for the synthesis of 6amino. A novel synthesis and characterization of fused pyridopyrimidine. Therapeutic potential of heterocyclic pyrimidine scaffolds ncbi.
The first reaction in this pathway, catalyzed by carbamoylphosphate synthetase cps, is common to both the pyrimidine and arginine biosynthetic pathways, as well as. This page was last edited on 20 january 2019, at 21. Habarakada liyanage, thakshila udayakanthi liyanage. A new series of 4substituted 2amino pyrido3,4dpyrimidine derivatives has been designed and synthesized as potential anticancer agents. In vitro cytotoxicity of pyrido2,3dpyrimidine derivatives against u937, thp1 and. Dec 15, 20 changing from the quinolone 1 to the analogous pyrido2,3dpyrimidine 2 improved the potency against dyrk1b to 0. Analysis of two polymorphic forms of a pyrido 2,3d pyrimidine n9c10 reversebridge antifolate binary complex with human dihydrofolate reductase. An easy synthetic access to spiro derivatives containing. Synthesis of imidazo1,2apyridines and pyrido 1,2a pyrimidines in water and their snar cyclizations. We report here a synthesis of new coumarone aldehyde, 4piprazino, 4morpholino, 5chromenopyrido2,3dpyrimidine and its.
We recently reported the identification of pyrido2,3 dpyrimidines as selective antioxidant23, antiinflammatory and highly analgesic properties2428. Compounds 6 ic 50 420 nm and 9 ic 50 930 nm are found to be better molecules in this. When treated with copperii acetate, the pyrido1,2apyrimidines. Information from its description page there is shown below. The reaction of compound 11 with ethyl cyanoacetate 2a gave the pyrido2. The replacement of the methyl group in 2 on the benzene ring by different halogens e. Cyclocondensation of 2arylmethylidene3fluoroalkyloxopropionates with 2aminopyridine occurs at both the polyfluoroacylvinyl and alkoxycarbonylvinyl fragments to give alkyl 4aryl2polyfluoroalkyl4hpyrido1,2apyrimidine3carboxylates and 4aryl2hydroxy3polyfluoroacyl4hpyrido1,2apyrimidines, respectively. Synthesis of novel pyrimidine derivative and its biological evaluation anshu chaudhary, pramod kumar sharma, prabhakar verma, and rupesh dudhe abstract. Buchwaldhartwig coupling reaction of substituted anilines with pivaloyl protected 2,4diamino6bromopyrido2,3dpyrimidine was successfully explored to synthesize these analogues.
A novel series of pyrido2,3dpyrimidines as selective and potent dhfr inhibitors against these opportunistic infections are presented. Pdf design and synthesis of a series of pyrido2,3d. Cyclocondensation of 2arylmethylidene3fluoroalkyloxopropionates with 2aminopyridine occurs at both the polyfluoroacylvinyl and alkoxycarbonylvinyl fragments to give alkyl 4aryl2polyfluoroalkyl4h pyrido 1,2a pyrimidine 3carboxylates and 4aryl2hydroxy3polyfluoroacyl4h pyrido 1,2apyrimidines, respectively. Uracil is a bifunctional nucleophilic substrate that readily reacts with electron deficient systems and yields pyrido2,3dpyrimidines. Pdf pyridopyrimidine derivatives as inhibitors of cyclic nucleotide.
Thus synthesized novel derivatives were confirmed by elemental analysis, ir, 1hnmr and ms. We report the discovery and optimization of a series of new pyrido3,4dpyrimidine based inhibitors via a structurebased hybridization approach from our previously reported inhibitor cct251455 and a modestly potent screening hit. In vitro cytotoxicity of pyrido 2,3dpyrimidine derivatives against u937, thp1 and. Design, synthesis, and molecular modeling of novel pyrido. Dec 18, 2012 tu s, zhang j, zhu x, xu j, zhang y, wang q, jia r, jiang b, zhang j 2006 new potential inhibitors of cyclin dependent kinase 4. Looking for online definition of pyridopyrimidine 2pyridones in the medical dictionary. Pyrido2,3dpyrimidine derivatives were synthesized regioselectivly in good to high yields by onepot threecomponent condensation of 6amino2methylthiopyrimidin43hone, aromatic aldehydes and ethylcyanoacetate or meldrums acid using 1,2dimethylnbutanesulfonic acid imidazolium hydrogen sulfate dmbsihso4 brrnstedacidic ionic liquid as catalyst.
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