Heterocyclization of thiouracil derivative: synthesis of thiazolopyrimidines, tetrazolopyrimidines and triazolopyrimidines of potential biological activity

Abdelghani, Essam; Said, Said Aly; Assy, M. G.; Hamid, Atef M. Abdel

doi:10.1007/s13738-015-0656-2

Cited by 18 publications

(8 citation statements)

References 20 publications

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“…In continuation of our efforts aiming to synthesize and evaluate the biological activities of new heterocycles , we report in this work a synthetic approach to a series of novel thienopyrimidine derivatives bearing furan moiety. Thus, thieno[2,3‐ d ]pyrimidine 3 was synthesized via alkylation of 2‐furan‐2‐yl‐4‐mercapto‐6‐methylpyrimidine‐5‐carbonitrile 1 with ethyl chloroacetate in the presence of sodium acetate as a mild base to give the S ‐alkylated derivative 2 , which underwent Thorpe–Ziegler cyclization upon refluxing with sodium ethoxide.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

Hamid

Shehta

2018

Journal of Heterocyclic Chem

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Cyclization of 2‐furan‐2‐yl‐4‐mercapto‐6‐methylpyrimidine‐5‐carbonitrile 1 with ethyl chloroacetate gave o‐aminoester thienopyrimidine derivative 3, which was reacted with a variety of reagents to give a series of novel thienopyrimidines including tetrazolyl thienopyrimidine, pyrrolylthienopyrimidine, pyrimidothienotriazine, and thienodipyrimidines. Some of the synthesized compounds were tested for their antibacterial activities against Gram‐positive and Gram‐negative bacteria.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

Hamid

Shehta

2018

Journal of Heterocyclic Chem

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“…2 In view of the above-mentioned facts, if two active pharmacophores, linked together, would generate novel molecular structures which are likely to exhibit interesting biological properties. Tetrazolo-pyrimidine condensed derivatives as the pharmacophore exhibit broad spectrum of biological activities encompassing antimicrobial, [3][4][5][6][7][8] antifungal, [9][10][11] anticancer, [12][13][14][15][16][17][18] antimalarial, 19 antitubercular, 19 anti-inflammatory, 20 analgesics, [21][22] antiviral, 23 anti-oxidant, 24 antiproliferative, [25][26] and antibacterial agents. 27 Hence the preparation of tetrazolo[1,5-a]pyrimidine core unit has gained much importance.…”

Section: Introductionmentioning

confidence: 99%

A Facile, Efficient and Catalyst Free Synthesis of Imidazole, Tetrazole and Pyrimidine Combined Moiety as Potential Antimicrobial and Antitubercular Agents

Joshi¹,

Panchani²

2021

HETEROCYCLES

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The tetrazole fused pyrimidine system possesses a broad spectrum of biological activities. So, we have synthesized 5-(substitutedphenyl)-7-(1Himidazol-4-yl)-4,7-dihydrotetrazolo [1,5-a]pyrimidine derivatives (5a-n) by reaction of chalcones with 5-aminotetrazole without catalyst in appropriate solvent. The structural elucidation of these compounds is based on MS, IR, 1 H-NMR and 13 C-NMR spectral data. The in vitro anti-microbial activity was investigated against Gram-positive and Gram-negative bacterial and fungal strains.It was found that the compounds 5a, 5b, 5c, 5d, 5e showed significant activities against tested organisms as compared to standard drugs (Ampicillin and Griseofulvin) while compounds 5a, 5c, 5i, and 5k showed good percentage of average inhibition in the dormant and active stage of tuberculosis.We carried out the synthesis of tetrazolo [1,5-a]pyrimidines in the acidic and basic catalytic amount at reflux temperature, but there was not much satisfied with the yield and reaction time of obtained products.Again the same reaction was carried out without any solvent or catalyst in fused condition but yield was very low. So from the above conclusion, we have chosen, an alcoholic solvents such as methanol, n-propanol, isopropanol, n-butanol and polar solvent like dimethylformamide (DMF) and 1,4-dioxane.After doing various optimizations in the experimental conditions, it was concluded that, when the reaction was carried out in n-butanol solvent showed better yield (87%) in less reaction time.All the newly synthesized compounds were characterized using IR, 1 H-NMR, 13 C-NMR, and mass spectroscopy. The IR spectrum of synthesized compounds exhibited characteristic absorption band at 3075 cm -1 for aromatic C=C stretching vibration band. Characteristic absorption band observed at 1315 cm -1 for C-N stretching in imidazole ring and at 1605 for C=N of the pyrimidine ring system and all other general frequency band are in good agreement with the structure. 1 H-NMR spectra of the compound 5b showed characteristic singlet signals at 12.16 ppm due to the proton of imidazole-NH and at 10.44 ppm due to the proton of fused pyrimidine-NH. Chiral carbon proton was observed doublet at 5.28 ppm with 2.80 Hz coupling constant value. The 1 H-NMR spectrum of compound 5c exhibited two doublets, arising from the two equivalent phenyl ring protons at 7.54 and 7.24 ppm. The 13 C-NMR spectrum of compound 5c showed signal at 53.23 ppm for the chiral carbon while at 96.00 ppm for the pyrimidine ring C=C carbon and at 21.12 ppm for the methyl carbon attached to phenyl ring. Molecular ion peak was observed in agreement with molecular weight of respective compound i.e. the molecular formula of compounds 5c and 5m by displaying molecular ion peaks at m/z 279 (M + ) and 325 (M + ) respectively. Scheme 1 PLAUSIBLE REACTION MECHANISM: Scheme 2The examination of the data of the Table 2 revealed that many of the compounds shown good activity against bacterial strain when compared with the standard drugs like Ampicillin, Chloramphenicol, and...

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“…[31] Changes in their structure have offered a high degree of diversity that has proven useful for the development of new therapeutic agents having improved potency and lowered toxicity. Based on the above considerations and in continuation of our research on biologically potent heterocyclic derivatives, [32][33][34][35][36][37][38] herein, we report the synthesis, structural elucidation and antidiabetic activity of some new azoles and azines prepared from commercially available reagents.…”

Section: Introductionmentioning

confidence: 99%

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

2017

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Various interesting heterocycle skeletons were synthesized via Michael type addition reaction with 1,2; 1,3-bidentate nitrogen and carbon nucleophiles. Cycloaddition of different α,β-unsaturated systems afforded bromopyrimidinone 3/5, bromothiazine 4 and bromopyrazole 6a/6b pyrazole-1-carboxylate 8, pyridinylmethanone 9, nicotinonitrile 10, pyrazolopyridine 11a/11b, pyran-3-carbonitrile 12/13, chromenopyridine 14 and N-butyrylpyrazolyl-1-butanone 15 derivatives. The structures of the synthesized compounds were elucidated based on IR, NMR and mass spectral analyses. Group of the newly synthesized compounds were screened for their anti-diabetic activities, whereas compounds 8 and 11b exhibited promising anti-diabetic activities at micro molar concentration against α-glucosidase inhibitor with IC50 values ranging between 13.80-500 μM. On the other hand compound 10 showed a week effect as compared to the standard anti-diabetic agent.

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Heterocyclization of thiouracil derivative: synthesis of thiazolopyrimidines, tetrazolopyrimidines and triazolopyrimidines of potential biological activity

Cited by 18 publications

References 20 publications

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

A Facile, Efficient and Catalyst Free Synthesis of Imidazole, Tetrazole and Pyrimidine Combined Moiety as Potential Antimicrobial and Antitubercular Agents

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

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