Synthesis of new pyrazolo1,5apyrimidine derivative. Method of treatment using substituted pyrazolo1,5a. Synthesis of new pyrazolo 1,5a pyrimidine, triazolo4,3a pyrimidine derivatives, and thieno. Synthesis and antitumor activity of some new pyrazolo3,4. Synthesis, characterization and biological evaluation of some. Onepot synthesis of some new pyrazole, pyrimidine, pyrazolo 1,5a pyrimidine and pyrido2,3d pyrimidine derivatives 2 figure 1. Synthesis and antitumor activity of novel pyrazolo 1, 5 a pyrimidine derivatives. A series of new pyrazolo1,5apyrimidine derivatives has been synthesized by using 7hydrazinyl. Pdf synthesis and study of the antiinflammatory properties.
The synthesis starts with transformation of commercially available 2acetylpyridine and acetylpyrazine with \n,\ \n\dimethylformamide dimethylacetal into the corresponding \e\3dimethylamino 1 heteroarylprop2en 1 ones. A chemical set in excess of 400 compounds was synthesized to give 3,6,7substituted pyrazolo 1,5apyrimidinecarboxamides 9. The pyrazolohydrazone 6 is then treated with either 2,4pentandione and enaminonitrile or arylsubstituted. The reaction of compound 11 with ethyl cyanoacetate 2a gave the pyrido2. We previously reported 18flabeled pyrazolo 1,5a pyrimidine derivatives. An example of a domino reaction in the synthesis of pyrazolo. The pyrazolohydrazone 6 is then treated with either 2,4pentandione and.
The invention relates to a pyrazolo 1,5a pyrimidine derivative as shown in the general formula 1, and pharmaceutically usable salts thereof. Synthesis of some novel pyrazolo1,5apyrimidine derivatives. Read synthesis of trifluoromethylpromoted functional pyrazolo 1,5 a pyrimidine and pyrazolo 5, 1 d 1,2,3,5tetrazine43 h ones, journal of fluorine chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at. Synthesis and biological evaluation of chalconelinked. Sep 22, 2010 read an example of a domino reaction in the synthesis of pyrazolo 1, 5 a pyrimidine derivative, chemistry of heterocyclic compounds on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Fathalla 1 archives of pharmacal research volume 22, article number. Treatment of 2a with malonodinitrile results in the substituted pyrazolo 1,5a pyrimidine 16. Chemistry central journal synthesis of some new pyrazolo 1, 5 a pyrimidine, pyrazolo 5, 1 ctriazine, 1,3,4thiadiazole and pyridine derivatives containing 1,2,3triazole moiety nadia a.
Abdelhamid 2 0 department of chemistry, faculty of science, benisuef university, benisuef 62514, egypt 1 department of chemistry, faculty of. Synthesis of pyrazolo1,5apyrimidine and pyrazolo3,4bpyridine 4hydroxy6methylpyran2one 2a 720 mg, 5. Synthesis and application of disazo reactive dyes derived. The present invention relates to and be used for the treatment of the autoimmunity relevant with interleukin 1 receptor associated kinase irak and the compound of inflammatory disease, more specifically, the present invention relates to the compound regulating irak1 and. One isomer of pyrazolopyrimidines, known as pyrazolo 1,5a pyrimidine, is the basis for a class of sedative and anxiolytic drugs related in terms of their effect to benzodiazepines. Jan 23, 2017 a novel series of pyrazolo 1, 5 a pyrimidine substituted diamides has been designed and synthesized using a linear mode multistep synthesis.
Pdf a simple highyielding procedure for the synthesis of novel pyrazolo1,5a pyrimidine analogues is reported via the condensation of 1. One of the most common methods for the synthesis of fluorinated pyrazolo 1,5a pyrimidine is the fluorination of the scaffold directly by electrophilic fluorination, 7 using a reagent like 1. In vitro antileishmanial and antitrypanosomal activity. Their synthetic routes have escalated dramatically in the last decades. They are considered as a key structural motif in many vital applications, such as medicinal, pharmaceuticals, pesticides, dyes and pigments.
This division compounds have attracted wide pharmaceutical interest because of their antitrypanosomal activity. A series of novel monoazodisperse dyes containing pyrazolo 1,5a pyrimidine structures were synthesized starting with the coupling reaction between ethyl cyanoacetate and 4hydroxybenzenediazonium chloride, followed by treatment of the resulting hydrazone product with hydrazine hydrate. A onepot process for the microwaveassisted synthesis of. Structure, properties, spectra, suppliers and links for. Pdf synthesis of new pyrazolo1,5apyrimidine, triazolo4. The general formula 1 is as shown in the specification. Elemental analysis data were taken on a perkinelmer 240c elemental analytical instrument. The pyrazolo 1, 5 a pyrimidine class of compounds has been identified as a privileged structure for library synthesis on the basis of several key characteristics of the core molecule. In nitration of this species the orientation of substitution is strongly reagent dependent. Synthesis of new pyrazolo1,5apyrimidine, triazolo4,3a hindawi. The synthesis of two series of 1 phenyl and 1h pyrazolo 3,4bpyridine is described. The ir spectrum of 17 showed bands due to nh 2 and nh functionalities in the region 33403150 cm. Onepot synthesis of some new pyrazole, pyrimidine, pyrazolo 1, 5 a pyrimidine and pyrido2,3d pyrimidine derivatives mohamed a. Thirteen examples of the conversion of 5amino3arylamino1hpyrazole4carbonitriles.
Pdf a simple highyielding procedure for the synthesis of novel pyrazolo1,5apyrimidine analogues is reported via the condensation of 1. As pyrazolo 1, 5a pyrimidine and thieno3, the 2b pyrimidine derivatives of irak4 conditioning agent. Full length article synthesis and antitumor activity of some new pyrazolo 3,4d pyrimidine and pyrazolo 3,4bpyridine derivatives e. Oct 24, 2014 in light of these facts and as a continuation of our previous work in the synthesis of novel compounds with promising biological applications 1416, we report herein the synthesis of new 5aminopyrazole and pyrazolo1,5apyrimidine derivatives and an examination of their. The invention further relates to application of the compound in. Preliminary biodistribution experiments of both compounds showed s slow clearance rate from excretory tissues which. Synthesis of a new series of pyrazolo 1,5 a pyrimidines structurally related to zaleplon. A series of pyrazolo 1,5a pyrimidines substituted at c5 with 1 phenylprop2en 1 one 6aq and 3phenylprop2en 1 one 7ak was synthesized and evaluated for antiproliferative activity.
Novel pyrazolo1,5apyrimidines as translocator protein. Synthesis and cytotoxic activity of new pyrazolo1,5apyrimidines and determination of pyrimidine regiospecific ring formation with 2d nmr. Synthesis, characterization, and cytotoxicity of some new 5. The pyrazolo 3,4bpyridine 7 was obtained in two steps. Pdf synthesis of some new pyrazolo1,5apyrimidine, pyrazolo5. Synthesis and biological evaluation of pyrazolo1,5a. Pdf synthesis and antitumor activity of novel pyrazolo1. Synthesis, effect of substituents on the regiochemistry.
Synthesis of some new pyrazolo1,5apyrimidine, pyrazolo5,1ctriazine, 1,3,4thiadiazole and pyridine derivatives containing 1,2,3triazole. Synthesis and biological evaluation of pyrazolo 1, 5 a pyrimidine compounds as potent and selective pim 1 inhibitors. Method of treatment using substituted pyrazolo 1,5a pyrimidine compounds. Synthesis of some new pyrazolo1,5apyrimidine, pyrazolo5,1ctriazine, 1,3,4 thiadiazole and pyridine derivatives containing 1,2,3triazole moiety. Cn102985426b as pyrazolo 1,5a pyrimidine and thieno3.
Synthesis of disazo pyrazolo1,5apyrimidines the procedures used for the synthesis of compounds a f, 16a 16c, 19a 19f and 22a 22f are represented by the preparation of compound a below. A chemical set in excess of 400 compounds was synthesized to give 3,6,7substituted pyrazolo 1, 5 a pyrimidinecarboxamides 9. Synthesis and biological evaluation of pyrazolo 1,5a pyrimidine compounds as potent and selective pim 1 inhibitors. Pyrazolo 1,5a pyrimidine 3carboxylic acid 95% cas number 25940356. Regioselective synthesis of novel substituted pyrazolo1,5a.
Synthesis of trifluoromethylpromoted functional pyrazolo. The 2alkynyl pyrazolo 1,5a pyrimidine derivatives have been explored as new and potential antiproliferative agents. Dichloro and diazido derivatives were obtained from the reaction of pyridopyrazlopyrimidine derivatives with pocl3 followed by nan3. Concluding, we have developed a simple, efficient, and versatile onestep method for the synthesis of functionalized pyrazolo1,5apyrimidines 5a h in a regiochemical manner by reaction between aminopyrazole 1 with the chromenone 4. A general cyclization route to pyrazolo 1, 5 a pyrimidines from 3aminopyrazole and 1,3dicarbonyl compounds is applied to synthesis of the parent ring system. Synthesis from 2,4dinitrobenzamide and tosylate precursors and comparative biological evaluation for tumor imaging with positron emission. They have beneficial properties as antimetabolites in purine biochemical reactions. Synthesis of sulfatoethylsulfone pyrazolo 1,2a pyrimidine reactive dyes 1 and 2. The synthesis of new pyrazolo1,5apyrimidine derivatives arkivoc. Khalil et al heterocyclic synthesis via enaminonitriles. Ultrasound assisted synthesis of 2alkynyl pyrazolo1,5a. Herein, we describe the synthesis of 3fluoro pyrazolo 1,5a pyrimidine starting from 3amino4fluoro pyrazole.
Synthesis of 3fluoro7heteroaryl2phenyl pyrazolo 1, 5 a pyrimidine derivatives. Most of the drugs from this class marketed to date are intended to induce sleep, and are prescribed for people suffering insomnia, however some newer compounds produce anxiolytic effects with. The regioselectivity was attributed to the high nucleophilicity of the amino group in 3amino5methyl1hpyrazole and the high electrophilicity of the. Recent research revealed that pyrazolopyrimidines and their derivatives have also been identified as bioactive compounds to use as neuroleptic agents and as tuberculostatic. Synthesis of new pyrazolo1,5apyrimidine, triazolo4,3apyrimidine derivatives, and thieno2,3bpyridine derivatives from sodium. Differential inhibition of pyrazolo1,5apyrimidine derivatives, epalrestat and sorbinil, on hakr1b1 4substituted7oxo4,7dihydropyrazolo1,5apyrimidinederivatives, 5a,dj,l, were tested as differential inhibitors at the concentration of 70 mm using either 0. Reaction of cinnamonitriles with 5amino4cyano3cyanomethylpyrazole. Synthesis of some new pyrazolo1,5apyrimidine, pyrazolo5,1ctriazine, 1,3,4 thiadiazole and pyridine derivatives containing 1,2,3triazole. We set out to explore a radiolabeled analog of pyrazolo 1,5a pyrimidine for use as a pet tumor imaging agent. Synthesis of pyrazolo1,5apyrimidine derivatives 4ai, 4lm 4j,k. Simple approach to the synthesis of 3fluoro pyrazolo1,5a. Compounds useful in the synthesis of compounds for treating pain, cancer, inflammation, neurodegenerative disease or typanosoma cruzi infection in a mammal. In the studies described in this publication, a new, simple and efficient route to 7substituted pyrazolo 1, 5 a pyrimidine 3carboxamides710 that have structures related to 1 3 has been developed.
Chemistry department faculty of science, bani suef, a. Ultrasound assisted synthesis of these compounds was carried out by using a multistep method involving the h3po3 mediated construction of pyrazolo 1,5a pyrimidine ring possessing a bromo group at c2 position followed by pdccu catalyzed. Synthesis of new pyrazolo1,5apyrimidine, triazolo4,3 a pyrimidine derivatives and thieno2,3bpyridine derivatives from sodium 3. A series of novel monoazodisperse dyes containing pyrazolo 1, 5 a pyrimidine structures were synthesized starting with the coupling reaction between ethyl cyanoacetate and 4hydroxybenzenediazonium chloride, followed by treatment of the resulting hydrazone product with hydrazine hydrate. Simple approach to the synthesis of 3fluoro pyrazolo1,5. Synthesis and study of the antiinflammatory properties of some pyrazolo 1, 5 a pyrimidine derivatives. General procedure for the synthesis of pyrazolo 1,5a pyrimidines 7, 10 and 15ad. Synthesis of new pyrazolo3,4bpyridines and pyrazolo1,5. Synthesis of new pyrazolo1,5apyrimidine, triazolo4,3a. Design and synthesis of some new pyrazolo 1,5a pyrimidines, pyrazolo 5, 1 ctriazines, pyrazolo 3,4dpyridazines, and isoxazolo3,4dpyridazines containing the pyrazole moiety abdou o. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. Pdf the synthesis of new pyrazolo1,5apyrimidine derivatives.
Synthesis of new substituted pyrazolo 1, 5apyrimidines and. Owing to the important biological properties of imidazo 1,2apyridines and pyrazolo 1,5a pyrimidines, synthesis of novel analogues containing these structures has attracted interest of several synthetic groups1519. Supporting information substituted pyrazolo1, 5apyrimidine. Chemistry central journal synthesis of some new pyrazolo 1,5a pyrimidine, pyrazolo 5, 1 ctriazine, 1,3,4thiadiazole and pyridine derivatives containing 1,2,3triazole moiety nadia a. Read synthesis and bzr affinity of pyrazolo 1,5 a pyrimidine derivatives. A onepot process for the microwaveassisted synthesis of 7.
A facile synthesis of pyrazolo 1,5apyridine derivatives. Synthesis and cytotoxic activity of new pyrazolo1,5a. Results and discussion synthesis the products 4ac, 5a c, 6a and 6b were obtained from the reaction between equimolar quantities of 3formylchromone derivatives 1ac, with the corresponding hydrazines 2a, 2b or aromatic amine 3 in anhydrous thf scheme 1. Abstracta new series of pyrazole, pyrimidine, pyrazolo1,5apyrimidine, imidazo1,2bpyrazole and pyrazolo5,1bquinazoline derivatives containing indane. One isomer of pyrazolopyrimidines, known as pyrazolo 1, 5 a pyrimidine, is the basis for a class of sedative and anxiolytic drugs related in terms of their effect to benzodiazepines.
Chemistry of heterocyclic compounds 2015, 50, 16081615. Pyrazolo 1,5apyridines are generally synthesized by intermolecular cyclization reactions of naminopyridine derivatives with alkene or alkyne derivatives. Facile and efficient synthesis of a new class of pyrazolo 1,5a pyrimidine derivatives via onepot multicomponent reactions. Condensation of 2a, 2c and 2d with ethylidenemalodintriles leads to racemic dihydro pyrazolo 1,5a pyrimidines 18ae. This compound could not be used as starting material for the preparation of indolo3,2. The pyrazolo 1,5a pyrimidine class of compounds has been identified as a privileged structure for library synthesis on the basis of several key characteristics of the core molecule. Raslan chemistry department, faculty of science, aswan university, 81528 aswan, egypt. Mixed nitric and sulfuric acids yield the 3nitro compound, whereas nitric acid in acetic anhydride yields the 6nitro compound. Compound 11 was used as a key intermediate for a facile synthesis of the title compounds 14, 15, 17, 21a,b, and 24ac where the reaction of 11 with some 1,3dielecrophiles resulted in the formation of pyrido2. The synthesis of new pyrazolo1,5apyrimidine derivatives. Cn104292233a pyrazolo1,5apyrimidine derivative and.
Structures of 18f labeled pyrazolo 1, 5 a pyrimidine derivatives. Pyrazolo 1,5a pyrimidines are fused nheterocyclic systems of a pyrazole. Out of 23 derivatives synthesized in the current study. Synthesis of new pyrazolo1,5apyrimidine derivative using 5. Acid derivatives of pyrazolo1,5apyrimidine as aldose. Synthesis of new pyrazolo 1, 5 a pyrimidine derivative using 5 aminouracil and ketene dithioacetal o. A simple and practical fourstep protocol for the parallel synthesis of 7heteroaryl pyrazolo 1,5 \a \ pyrimidine 3carboxamides was developed. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Synthesis of disazo pyrazolo1,5apyrimidines sciencedirect. Pdf synthesis and antitumor activity of novel pyrazolo1,5. Synthesis of some new pyrazolo1,5apyrimidine, pyrazolo5,1.
A series of novel pyrazolo 1,5a pyrimidines, closely related to n,ndiethyl2242fluoroethoxyphenyl5,7dimethylpyrazolo 1,5apyrimidin3ylacetamide 2, dpa714, were synthesized and biologically in vitro evaluated for their potential to bind the translocator protein 18 kda tspo, a protein today recognized as an early biomarker of neuroinflammatory processes. Thus, reacting 5 amino 1 phenylpyrazole with chalcone analogues gave 4,6diarylpyrazolo3,4bpyridine derivatives. Synthesis of bissulphatoethylsulphone pyrazolo 1,5a pyrimidine bifunctional reactive dye 1 scheme 2 a solution of pabses diazonium chloride d1 0. Synthesis of some new pyrazolo 1, 5a pyrimidine, pyrazolo 5, 1c.
Synthesis of new substituted pyrazolo1,5apyrimidines. Synthesis and application of novel bifunctional pyrazolo. Synthesis and antiinflammatory evaluation of some new pyrazole. Reaction of diene 20 with the heterodienophile 21 leads. Synthesis of some new pyrazolo1,5apyrimidine, pyrazolo. Synthesis and in vitro cytotoxic activity of novel. Pdf synthesis of new pyrazolo1,5apyrimidine, triazolo. Synthesis of some new pyrazolo1,5apyrimidine, pyrazolo5,1ctriazine, 1,3,4thiadiazole and pyridine derivatives containing 1,2,3triazole moiety. Utility of anilides as building block to synthesize some. Differential inhibition of pyrazolo 1,5a pyrimidine derivatives, epalrestat and sorbinil, on hakr1b1 4substituted7oxo4,7dihydropyrazolo 1,5apyrimidinederivatives, 5a,dj,l, were tested as differential inhibitors at the concentration of 70 mm using either 0. To facilitate the rapid preparation of this library, a preparative strategy included the. Compared to the classical method negishi coupling, this new procedure has the advantages of convenient manipu. Synthesis and antitumor activity of some new pyrazolo1,5a.
Believes versus evidencebased regioorientation in the. A simple highyielding procedure for the synthesis of novel pyrazolo 1,5a pyrimidine analogues is reported via the condensation of 1,3diketones or keto ester with substituted 5 aminopyrazoles. Synthesis and bzr affinity of pyrazolo1,5 a pyrimidine. Synthesis of new pyrazolo 1,5a pyrimidine derivative using 5aminouracil and ketene dithioacetal o. These new compounds were screened for their in vitro antiproliferative activity using an mtt assay. The general structural formula for pyrazolo1,5apyrimidines of pharmacological, medicinal. In conclusion, we have elaborated a simple approach for the synthesis of 3fluoro pyrazolo 1, 5 a pyrimidine derivatives by introducing the fluorine at an earlier stage of the synthesis instead of using a direct electrophilic fluorination on the pyrazolo 1, 5.
Among them, 6h was found to be the most active compound against the mdamb231 cell line with an ic50 of 2. An efficient synthesis of pyrazolo1,5apyrimidines and evaluation of. Etman a department of chemistry, faculty of science, mansoura university, et35516 mansoura, egypt b textile research division, national research centre, 12622 dokki, giza, egypt. Pyrazolo 1, 5 a pyrimidine based compounds have been employed in the dye industries, for example, azopyrazolo pyrimidine dyes. Ranjana aggarwal, eakta masan, pawan kaushik, dhirender kaushik, chetan sharma, k. These compounds present a privileged core from a biological point of view. The synthesized compounds were characterized by 1h nmr, c nmr, esims and ir analyses. Jun 12, 2017 pyrazolo 1, 5 a pyrimidines are purine analogues. An efficient synthesis of 7substituted pyrazolo1,5apyrimidines using a onepot, twostep process via pdcatalyzed direct charylation followed by a saponificationdecarboxylation reaction is reported. Synthesis of pyrazolo 1,5a pyrimidine and pyrazolo 3,4bpyridine 4hydroxy6methylpyran2one 2a 720 mg, 5. An efficient synthesis of 7substituted pyrazolo 1,5a pyrimidines using a onepot, twostep process via pdcatalyzed direct charylation followed by a saponificationdecarboxylation reaction is reported. Synthesis and antitumor activity of novel pyrazolo 1,5a pyrimidine derivatives article pdf available september 2011 with 90 reads how we measure reads. Synthesis and application of novel bifunctional pyrazolo 1, 5 a pyrimidine reactive dyes magda m. Ahmed, synthesis of some pyridothienopyrazolopyrimidopyrimidine and.