Monopropargyl pyrimidine nucleobases uracil and thymine are versatile building blocks for the synthesis of biologically relevant 1,2,3 triazoles 11. Ctp is a feedback inhibitor of the pathway, and atp is a feed. Results we have described herein the synthesis of 12 hybrid 1,2,4triazole schiff bases bearing. Synthesis and pharmacological evaluation of some new. Scheme 3 describes the synthesis of compound 15, which has scaffold i, but with an oxadiazole instead of a triazole linking the pyrimidine and the phenyl rings. Novel nitrogen heterocycles containing pyrimidine and. Synthesis and investigation of antioxidant and antiinflammatory activity.
View the article pdf and any associated supplements and figures for a period of 48 hours. The high reactivity of the strained threemembered 2hazirine ring facilitated the unusual cyclization of electrondeficient dienes with electrondeficient dienophiles. Reynolds, drug discovery division, southern research institute, 2000 ninth avenue south, birmingham, alabama 35205, united states s supporting information. Chapter 1 synthesis and biological evaluation of 1,2,4triazolo1,5apyrimidines 1. Synthesis, antibacte rial, antifungal, microwave, triazole, pyrimidine. Monopropargyl pyrimidine nucleobases uracil and thymine are versatile building blocks for the synthesis of biologically relevant 1,2,3triazoles 11. Synthesis and characterization of pyrimidine bearing 1,2,4. An efficient method has been described for synthesis of 6substituted aryl43, 5diphenyl1h1,2,4triazol1yl1, 6dihydropyrimidine2thiol, as a beneficial antimicrobial, anticonvulsant and anticancer agents. The pyrimidine ring system is a six membered heterocyclic ring structure composed. All the compounds have shown c n peak in 22202200 cm. Chapter ii synthesis of 1,2,4triazole derivatives and. This regulation ensures that a balanced supply of purines and pyrimidines exists for rna and synthesis. They are generally used as starting material for the synthesis of triazole nucleosides 1219, triazole nucleotides 2023, oxiconazole analogues 24, nucleopeptides 25.
Herein, we report the synthesis and preliminary biological evaluation of a diverse library of 181 purine, pyrimidine, and 1,2,4triazole acetamide analogues which were prepared in a high throughput solutionphase parallel reaction format under the pilot scale library program of the nih roadmap initiative. This has the practical advantage of giving the researcher experience in the reactions required in the synthesis. Appala raju2, popat baban mohite3, ramdas bhanudas pandhare3 1 research scholar, department of pharmacy,vinayaka missions university, salem, sankari main road, nh47,tamilnadu, india. Novel pyrimidine and its triazole fused derivatives. An efficient and straightforward methodology for the preparation of novel functionalized thiazolo3,2btriazole, triazolo1,5apyrimidine and triazolo3,4b1,3,4thiadiazine has been implemented with excellent yields via a onepot catalystfree procedure at room temperature by the reaction of dibenzoylacetylene.
Pdf synthesis and antimicrobial evaluation of some. Green synthesis of triazole derivatives with pyrimidine moiety. Research article green synthesis of triazole derivatives with pyrimidine moiety. Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the sixmember ring. The synthesis of 1,2,3 triazole 5substituted uracil furanonucleosides 4ae and 5substituted uridines 6ae, is reported. Abdelhamid 2 0 department of chemistry, faculty of science, benisuef university, benisuef 62514, egypt 1 department of chemistry, faculty of. Synthesis of nheterocycles synthesis of 1,2,4triazoles. Baran, richter essentials of heterocyclic chemistryi heterocyclic chemistry o s n n h n h n h o o n o n s n n h n n h hn n h n n h n n h h o n n h o h s n s s h n n n o o n n h h n n n n ss n n n s n n o n n n h nn s furan pk a. Consequently the 1,2,4triazolo4,3apyrimidine 4 was assigned to this reaction product which is also observed by earlier workers2324. Ultrasound assisted synthesis of triazoletetrazole. Then the mixture was stirred for 24 hrs at room temperature. Nsubstituted pyrimidine and pyrrolo2,3dpyrimidine derivatives have a great role in modern medicine and have shown rather marked antitumor and antimicrobial activities.
Heterocycles bearing a symmetrical triazole moiety were reported to show a broad spectrum of pharmacological properties like anticancer, 1,2 antimicrobial, 36 anticonvulsant, 7 antiinflammatory, analgesic 8,9 antidepressant, 10 antitubercular, 11,12 antimalarial and hypoglycemic 14 activities. Read design and synthesis of novel 1,2,3triazolepyrimidine hybrids as potential anticancer agents, european journal of medicinal chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. One step synthesis of highly functionalized thiazolo3,2b. Moreover, the prepared catalyst was characterized by the ft. The desired heterocyclic compounds were obtained in good yields and characterized by nmr, ir, and high resolution mass spectrometry. The green synthesis of triazole derivatives with pyrimidine moiety t. Chemistry central journal synthesis of some new pyrazolo1,5a pyrimidine, pyrazolo5,1ctriazine, 1,3,4thiadiazole and pyridine derivatives containing 1,2,3triazole moiety nadia a. Design and synthesis of novel 4hydrazone functionalized1. Introduction dihydropirimidinone s dhpm1 is an important class of compounds due to t. Solutionphase parallel synthesis of acyclic nucleoside libraries of purine, pyrimidine, and triazole acetamides ashish k. Department of chemistry, georgia state university, atlanta, ga, 30303 usa. The 1hnmr spectrum of 4g indicated the presence of a single triazole signal at. 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 250 the other diazines are pyrazine nitrogen atoms at the 1 and 4 positions and pyridazine nitrogen atoms at the 1 and 2 positions.
Baran, richter essentials of heterocyclic chemistryi. Design, synthesis and evaluation of triazolepyrimidine. A series of novel 2substituted 4hydrazone functionalized pyrido2,3dpyrimidine 8af and 9ae and 1,2,4triazole fused pyrido2,3dpyrimidine derivatives 10af and 11ae were prepared starting from ethyl 2amino6trifluoromethylnicotinate 3 via acylation, cyclization, chlorination, hydrazine reaction, hydrazone formation followed by intramolecular cyclization. Synthesis and antioxidant activity of 1,2,4triazole. Pyrimidine rings are assembled from bicarbonate, aspartate, and ammonia. The pyrimidine synthesis is a similar process than that of purinespurines synthesis. The clalcones of title compounds were synthesized in three steps and subsequently these chalcones were further reacted with thiourea in the presence of koh in. The presence of the triazole group between the sugar and the base of the inhibitor is of primary importance for efficient inhibition, while the insertion of a substituent at the 5 pyrimidine position results to a less potent inhibitor of ribonuclease a.
Atp stimulates the aspartate transcarbamoylase reaction, while ctp inhibits it. Synthesis of fused mercaptothione1,2,4triazole heterocycles 3. All the pyrimidines and their 1,2,4 triazole fused pyrimidine derivatives were synthesized and confirmed by physical data, ir, 1 h nmr, mass spectra and elemental analysis. Multicomponent click synthesis of new 1,2,3triazole.
Solutionphase parallel synthesis of acyclic nucleoside. Yet the synthesis of relatively simple, albeit important, 1. Design and synthesis of novel 1,2,3triazolepyrimidine. Synthesis and structure of drimane sesquiterpenoids. Several oxadiazole, triazole, and thiadiazole moieties were incorporated into the pyrimidine backbone. Ir spectroscopy, xrd, bet, sem, and icp techniques. General procedure for the synthesis of 8ah and 9ah by conventional method and ultrasound irradiation scheme 2 2. Drimenic acid was synthesized in six steps from norambreinolide. A simple, efficient, and mild method for the synthesis of substituted 1,2,4triazoles from hydrazines and formamide proceeds smoothly under microwave irradiation in the absence of a catalyst and shows excellent functionalgroup tolerance. A series of new mono1,2,3triazole derivatives of pyrimidine nucleobases were synthesized by onepot coppericatalyzed 1,3dipolar cycloaddition reactions between n1propargyluracil and thymine, sodium azide and several benzyl halides. Acyl hydrazides and triazoles as novel inhibitors of mammalian cathepsin b and cathepsin h. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine.
In view of the biological impovtance of these 1,2,4triazoles, several methods have been developed for the synthesis of this class of compounds. Synthesis and antioxidant activity of 1,2,4triazole linked thieno2,3 dpyrimidine derivatives volume. Mild and ecofriendly tandem synthesis of 1,2,4triazolo 4. Further, pyrimidine, fused heterocyclic pyrimidine derivatives and dihydropyrimidones are well known for their potential biological activity such as antiviral,antitumor.
A useful and efficient procedure was obtained for the synthesis of 1,2,3. In addition, the reaction course leading to the formation of 8 from the triazole methylenemlonnitrile scheme 2 can be assumed to proceed through the formation of cabanion fallowed by nucleophilic addition at the ethylenic bond and cyclization to give 8. This type is the most useful and widely used one for the construction of a pyrimidine ring from nonheterocyclic precursors. Synthesis of the target compounds was materialized starting from 2oxo6thiophen2yl2,3dihydropyrimidine4carbohydrazide 4. The next logical step in the process was to produce model compounds. Pyrimidines are heterocyclic, sixmembered, nitrogencontaining carbon ring structures, with uracil, cytosine and thymine being the basal structures of ribosecontaining nucleosides uridine, cytidine and thymidine respectively, or. Synthesis of some new pyrazolo1,5apyrimidine, pyrazolo. The chemistry of mercapto and thione substituted 1,2,4. Synthesis and pharmacological evaluation of some new pyrimidine derivatives containing 1,2,4 triazole shantaram gajanan khanage1, s.