R 1 is selected from the group consisting of hydrogen, halogen, cyano, carboxylic acid, acyl, thioacyl, alkoxycarbonyl, acyloxy, carbonate, carbamate, c 17 alkyl, aryl, amino, acetamido, nprotected amino, mono or di c 17 alkylamino, mono or di arylamino, mono or di c 310 cycloalkylamino, mono or di. For evaluating the hca i and ii inhibitory effect, all compounds were subjected to hca i and ii inhibition assay with co 2 as a substrate. Rao a a quinazoline and pyrido 3,2d pyrimidine based compound library was designed, synthesized and. A clean procedure for synthesis of pyrido d pyrimidine derivatives under solvent free conditions catalyzed by zro2 nanoparticles authors. A pyrido 3,2d pyrimidine derivative according to any of claims 1 to 4, wherein r3 is a monosubstituted or disubstituted phenyl group, wherein at least one substituent of said phenyl group is located in meta position with respect to the pyrido 3,2dpyrimidinyl core, or a pharmaceutically acceptable addition salt or a stereochemical isomeric. Inhibition of wildtype and mutant bcrabl by pyrido. Pyrido3,2dpyrimidines useful for treating viral infections. Catabolism of pyrimidine nucleotidenucleotiderupendra. These observations suggest that f may exist in different tautomeric forms within doublehelical and triplehelical complexes. Meaning of pyrido pyrimidine 2pyridones medical term. One of the three diazines sixmembered heterocyclics with two nitrogen atoms in the ring, it has the nitrogen atoms at positions 1 and 3 in the ring. The nucleophilic ammonia attacks carboxyphosphate to give carbamate.
Mnzif8 based zinc titanate nano catalyst exhibit excellent catalytic activity for synthesis of pyrano 2,3dpyrimidinone and pyrido 2,3dpyrimidine derivatives. Cds005243 sigmaaldrich 1hpyrido2,3dpyrimidine2,4dione aldrich cpr. The use of trimethylphosphite instead of phosphanes yields with2b the expected trimethoxyphosphazene3c, whereas2a reacts to the. Biological evaluation of indolylchalcone and pyrido2,3dpyrimidine derivatives for hca i and hca ii inhibitory activities. A facile clean synthesis of pyrido 2,3d pyrimidine and. Synthesis and in vitro inhibition effect of new pyrido2,3d.
Synthesis and in vitro inhibition effect of new pyrido2,3. A series of 6bromo32morpholino methyl amino6substituted. Reduction of 6azidouracils2 with hydrogen palladium or sodium dithionite afforded the corresponding 6aminouracils5 which could also be obtained by reaction of2 with triphenylphosphanevia phosphazenes and subsequent hydrolysis staudinger reaction. Definition of pyridopyrimidine 2pyridones in the medical dictionary by the free dictionary. A series of pyrido2,3dpyrimidine derivatives were designed and synthesized based on known cc chemokine receptor 4 ccr4 antagonists. Design, synthesis and molecular modeling of novel pyrido2,3. New approach for the synthesis of pyrido1,2apyrimidines. Changing from the quinolone 1 to the analogous pyrido2,3dpyrimidine 2 improved the potency against dyrk1b to 0. Synthesis, antitumor activity, and docking analysis of new pyrido3. Us4681882a 4alkoxypyrido2,3dpyrimidine derivatives. Pdf a novel synthesis and characterization of fused. Predicted data is generated using the us environmental protection agencys episuite. In cps ii the first step of the reaction is the activation of bicarbonate by atp to form carboxyphosphate. Fourteen different 6amino,4substituted phenyl2oxo4substituted.
Tetrazoliumbased proliferation assays with baf3 cells transformed with bcrabl wildtype were performed. On the other hand, it reacted with some halo compounds to give the imidazo1. We recently reported the identification of pyrido2,3 dpyrimidines as selective antioxidant23, antiinflammatory and highly analgesic properties2428. The efficiency of elemental sulfur for the synthesis of 2h. Introduction 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 reductase dhfr such as pneumocystis. Evaluation of pyridopyrimidine derivatives ixii as cgmp and camp. Journal of chemical and pharmaceutical research, 2016, 83. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. Sequence specificity of the nonnatural pyrido2,3 d. Herein, we report the identification of a highly potent and selective erk5 inhibitor bay885 by highthroughput screening and subsequent structurebased optimization. A series of pyrido 2,3d pyrimidine derivatives were designed and synthesized based on known cc chemokine receptor 4 ccr4 antagonists. In vitro inhibition effects of indolylchalcones and new pyrido 2,3d pyrimidine derivatives on purified human carbonic anhydrase i and ii hca i and ii were investigated by using co 2 as a substrate.
Pdf an efficient synthesis of pyrido2,3dpyrimidine derivatives. Read synthesis and antitumor activity of pyrido 2,3 d pyrimidine and pyrido2,3 d 1,2,4triazolo4,3 a pyrimidine derivatives that induce apoptosis through g 1 cellcycle arrest, european journal of medicinal chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Files are available under licenses specified on their description page. We report here a synthesis of new coumarone aldehyde, 4piprazino, 4morpholino, 5chromenopyrido2,3dpyrimidine and its. The availability of a chemical probe to study the role of a specific domain of a protein in a concentration and timedependent manner is of high value. 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. Herein, we report the solvent free approach to synthesis of 4,7dioxo5,8diphenyl3,4,7,8. Application of quinazoline and pyrido3,2dpyrimidine. Pyrido, dpyrimidine structural motif is present in pirenperone tranquilizer and ramastine antiallergic, as well as in some antiulcerative and.
Aug 18, 2014 read synthesis and antitumor activity of pyrido 2,3 d pyrimidine and pyrido 2,3 d 1,2,4triazolo4,3 a pyrimidine derivatives that induce apoptosis through g 1 cellcycle arrest, european journal of medicinal chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Solventfree reaction conditions are of great interest because they are clean, efficient and reduce the use of organic solvents. Mnzif8 based zinc titanate nano catalyst was prepared by simple method. We screened different pyrido pyrimidine with cells expressing wildtype and mutant bcrabl. Looking for online definition of pyrido pyrimidine 2pyridones in the medical dictionary. Structureactivity correlations for three pyrido2,3d. Glutamine is then hydrolyzed to give glutamate and free ammonia. We report here a synthesis of new coumarone aldehyde, 4piprazino, 4morpholino, 5chromeno pyrido 2,3d pyrimidine and its analogous. 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. Bicyclic and tricyclic fused pyrimidine derivatives have received much attention in connection with biologically signi cant systems such as pyrido, dpyrimidines. The first reaction is the conjugation of carbamoyl phosphate and aspartate to make n. Research article an efficient, clean, and catalystfree. Recent developments in the mcrs synthesis of pyridopyrimidines and spiropyridopyrimidines. Following the discovery of the very high inhibitory ability of the 43bromophenylaminoquinazolines against the tyrosine kinase activity of the epidermal growth factor receptor egfr e.
For reason of their vasospasmolytic effects these compounds are mainly indicated for the treatment of cerebral, cardiac, and peripheral vascular diseases such as myocardiac ischemia, cerebral infarction, pulmonary thromboses, as well as in cases of arteriosclerosis and other stenotic disorders. Introduction of a hydroxy group in position 6 or 9 gave an enhancement of the inhibitory potency compare 18, 19, 28, and 29 vs and 14. To investigate changes in the metabolic activity, all the compounds were incubated for 1 hour, 24 hours and 48 hours in protein free medium. A clean procedure for synthesis of pyridodpyrimidine derivatives under solventfree conditions catalyzed by zro2 nanoparticles volume. Also, it diazotized to give the corresponding diazonium chloride that is coupled. To a magnetically stirred mixture 6amino uracil or 1, 3dimethyluracil 1 mmol, malononitrile 1. The results showed that all compounds inhibited the hca i and hca ii enzyme activities. A pyrido3,2dpyrimidine derivative having the general formula. Onepot synthesis of new pyrido 2,3d pyrimidine derivatives under. Nitrogen containing heterocyclic ring such as pyrimidine is a promising structural moiety for drug designing. Erk5 is a key integrator of cellular signal transduction, and it has been. Pyrido1,2apyrimidin4one derivatives as a novel class of. For preparation of pyrido 2, 3dpyrimidine, threecomponent condensation of 6amino uracil or 1,3dimethyluracil with arylaldehydes and malononitrile has been carried out over nanocrystalline email protected in water and ethanol.
Synthesis and antitumor activity of new pyrido2,3 d. The nonnatural pyrido2,3 dpyrimidine nucleoside f, which pairs preferentially with guanine g and adenine a within doublehelical dna, recognizes with high selectivity at base pairs within triplehelical complexes. Thus, further reaction of 8chlorothieno3,2dpyrimidine 4 with various. Design, synthesis and molecular modeling of novel pyrido2. The activities of all the newly synthesized compounds were evaluated using a chemotaxis inhibition assay. Pdf a series of pyrido2,3dpyrimidines derivatives have been prepared by. An efficient synthesis of pyrido2,3dpyrimidine derivatives via onepot threecomponent reaction in aqueous media. Results pyridopyrimidines specifically inhibit the growth of bcrabl transformed cells. Design and synthesis of a series of pyrido2,3dpyrimidine. The ir spectrum of 17 showed bands due to nh 2 and nh functionalities in the region 33403150 cm. Application of quinazoline and pyrido 3,2d pyrimidine templates to design multitargeting agents in alzheimers disease tarek mohamed,ab mandeep k.
Various thieno3,2bpyridine, thieno2,3dpyrimidine and thieno3,2dpyrimidine skeletons have frequently attracted the interest of medicinal. Pdf synthesis and biological evaluation of pyrido 2, 3d. Discovery and characterization of the potent and highly. Efficient onepot synthesis of pyrano2,3dpyrimidinone and. Efficient onepot synthesis of pyrano2,3dpyrimidinone. Pdf new approach for the synthesis of pyrido1,2apyrimidines. Shahrzad abdolmohammadi and saeed balalaie affiliation. Mutations occur at positions that determine specific contacts of imatinib to the atpbinding site. The reaction, catalyzed by cheap and nontoxic bicl 3, proceeds with short reaction times under mild conditions and normal atmosphere. Pyrido4,3 dpyrimidine c7h5n3 cid 19883218 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. Pyrido1,2apyrimidin4one derivatives as a novel class.
Dec 15, 20 changing from the quinolone 1 to the analogous pyrido2,3dpyrimidine 2 improved the potency against dyrk1b to 0. Synthesis of some pyrido 2,3d pyrimidine ring system synthesis of pyrido 2,3d pyrimidine derivatives was performed according to the following general strategies. All structured data from the file and property namespaces is available under the creative commons cc0 license. Structural modification of diaminopyrroloquinazoline series resulted in pyrido 2,3d pyrimidine 2,4diamine series which was further optimized to give compounds 5 and 24 as potent, selective except tcell phosphatase ptp1b inhibitors with good mouse pk properties. This page was last edited on 20 january 2019, at 21. Synthesis and biological evaluation of pyrido 2, 3 d pyrimidinecarboxylate derivatives article pdf available in research journal of pharmaceutical, biological and chemical sciences 21. Characterization data of selected compounds are as follows. However, the pyrido3,2dpyrimidine isomer is the least described in the literature because of its difficult and expensive syntheses. First metalfree synthesis of tetracyclic pyrido and pyrazino. The present invention relates to a novel pyrido2,3 dpyrimidine derivative having the formula 1. The pyrido2,3dpyrimidine scaffold is stabilized by a pistacking interaction with phe36 and with side chain carbon atoms of met33 not shown and leu25. A series of novel pyrido 2,3d pyrimidine was efficiently synthesized in higher yield and it was subjected to antibacterial and antifungal activity.
Compound 6b was proven to be a potent ccr4 antagonist that can block cell chemotaxis induced by macrophagederived chemokine mdc, thymus and activation. Pyrido2,3dpyrimidine2,4dione uracil eef2k inhibitor kinase inhibitor homology modeling abstract a small molecule library of pyrido2,3dpyrimidine2,4dione derivatives 616 was synthesized from 6amino1,3disubstituted uracils 18, characterized, and screened for inhibitory activity against eukaryotic elongation factor2 kinase eef2k. Shahrzad abdolmohammadi, department of chemistry, east tehran branch, islamic azad university, po box 33955163, tehran, iran. Thirteen pyrido2,3dpyrimidine analogues were examined that differed in the substituents located at position 2 of the pyrimidinering see fig. Pyrido1,2 apyrimidines mol id structure formula chemical name mw id number cas number 10 ch11cl2n3o4s 2methoxycarbonyl methylthio7methyl4dichloromethylene3. We recently reported the identification of pyrido 2,3 dpyrimidines as selective antioxidant23, antiinflammatory and highly analgesic properties2428. Biosynthesis uridine monophosphate ump is synthesized first ctp is synthesized from ump pyrimidine ring synthesis completed first. Department of chemistry, east tehran branch, islamic azad university, po box 33955163, tehran, iran. Synthesis and pharmacological screening of pyridopyrimidines as.
One pot synthesis of novel cyanopyridones as an intermediate. Changing from the quinolone 1 to the analogous pyrido 2,3d pyrimidine 2 improved the potency against dyrk1b to 0. International journal of organic chemistry 2012, 02 01, 714. Introduction 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 reductase dhfr such as pneumocystis. Structure, properties, spectra, suppliers and links for. We aimed to examine whether pyrido pyrimidine type kinase inhibitors were capable of inhibiting both wildtype and mutant forms of bcrabl. 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. Cds005243 1hpyrido2,3dpyrimidine2,4dione email this page to a friend. A clean procedure for synthesis of pyridodpyrimidine. Synthesis of imidazo1,2apyridine, pyrido1,2 apyrimidine, and 3cyanocoumarin article pdf available in monatshefte fuer chemiechemical monthly 14812 october 2017 with 86 reads. A novel synthesis and characterization of fused pyridopyrimidine derivatives.
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