An Alternative Regioselective Approach for the Synthesis of Highly Functionalized Derivatives of Pyrazolo[5,1‐<i>b</i>]purine Scaffold

Sheikhi‐Mohammareh, Seddigheh; Shiri, Ali

doi:10.1002/jhet.3242

Cited by 18 publications

(3 citation statements)

References 29 publications

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“…These methods have shown multistep reactions in the construction of pyrido[1,2- e ]purine structures. As a continuation of our previous studies, − herein, we report a two-step, one-pot synthesis of pyrido[1,2- e ]purine derivatives, and considering the physicochemical and pharmacokinetic predictions, their inhibitory activity against SARS-CoV-2 3CL pro is evaluated using molecular docking and molecular dynamics approaches.…”

Section: Introductionmentioning

confidence: 99%

Pyrido[1,2-e]purine: Design and Synthesis of Appropriate Inhibitory Candidates against the Main Protease of COVID-19

et al. 2022

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A series of tricyclic and polycyclic pyrido[1,2- e ]purine derivatives were designed and synthesized via a two-step, one-pot reaction of 2,4-dichloro-5-amino-6-methylpyrimidine with pyridine under reflux conditions. Various derivatives of pyrido[1,2- e ]purine were also synthesized by substituting the chlorine atom with secondary amines. After careful physiochemical and pharmacokinetic predictions, the inhibitory effects of the synthesized compounds against the main protease of SARS-CoV-2 have been evaluated by molecular docking and molecular dynamics approaches. The in silico results revealed that among all of the studied compounds, the morpholine/piperidine-substituted pyrido[1,2- e ]purine derivatives are the best candidates as effective inhibitors of SARS-CoV-2.

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Section: Introductionmentioning

confidence: 99%

Pyrido[1,2-e]purine: Design and Synthesis of Appropriate Inhibitory Candidates against the Main Protease of COVID-19

et al. 2022

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“…[69,70] Some other miscellaneous procedures for the synthesis of mentioned amino-selenazoles are solid-state synthesis employing a Lewis acid catalyst [71] and aqueous phase one-pot synthesis under supramolecular catalysis. [69,72] Taking into account the biological importance of the selenium-containing organic compounds and as a part of our ongoing endeavor toward developing novel heterocyclic architectures of potential pharmacological significance, [23,[73][74][75][76][77][78][79][80] the present investigation is connected with the elaboration of synthetic protocols, antibacterial, antifungal and cytotoxic studies on the new derivatives of a novel [1,3]selenazolo [4,5-d] pyrimidine heterocyclic system 3 a-i.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents

et al. 2020

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A number of diversely functionalized derivatives of a novel [1,3]selenazolo[4,5‐d]pyrimidine have been synthesized through heterocyclization of some 2,4,5‐trisubstituted‐1,3‐selenazoles with orthoesters in refluxing acetic acid. The synthetic compounds were evaluated for their antimicrobial activity against a panel of microorganisms including Gram‐negative bacteria, Gram‐positive bacteria, and pathogenic fungi. The antifungal results revealed that the new selenium‐containing heterocycles were as good as or sometimes better than terbinafine and fluconazole. The in vitro anticancer activities of aforementioned heterocyclic compounds were screened against human breast carcinoma MCF‐7 and HeLa cervical cancer cells as well as HDF (human dermal fibroblast) normal cells. Antiproliferative results indicated that compounds with piperidine moiety on MCF‐7 cells and with morpholine moiety on HeLa cells exhibited well broad‐spectrum of anticancer activities with 397, 298 and 235 μM and 533, 390 and 204 μM of IC50 values after 24, 48 and 72 h of treatments, respectively, while they had no significant toxic effects on normal cells.

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“…On the basis of the ease of access to vinamidinium salts as fascinating precursors and due to our abiding interest in synthesis of potentially bioactive heterocyclic scaffolds [27][28][29][30][31][32][33][34][35], we have continued to explore the synthetic utility of these salts for the synthesis of novel 5-bromo-4-methyl-6-pyrazolylpyrimidines appended with various secondary amine substituents. To diverse antimicrobial libraries, their antibacterial and antifungal capacities were assessed against nine pathogenic strains.…”

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Synthesis and antimicrobial/antioxidant evaluation of novel pyrimidine-based derivatives with pendant pyrazoles using vinamidinum salts

Maghamifar

Sheikhi‐Mohammareh

Shiri

et al. 2023

Preprint

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Synthesis of a variety of 5-bromo-4-methyl-2-substituted pyrimidines endowed with pyrazolyl appended in C4 position is described via treatment of 5-bromo-4-hydrazineyl-6-methyl-2-substituted pyrimidines (6a–f) and vinamidinum salt of (E)-N-(3-(dimethylamino)-2-phenylallylidene)-N-methylmethanaminium perchlorate (5) in good to excellent yields. The inhibitory and hydrogen-atom donating abilities of the synthesized products were assessed against nine pathogens including six bacterial strains (both Gram-negative and Gram-positive), three fungal strains and DPPH free radicals. Notable antioxidant properties were not observed with the products. The inhibition zone diameters were determined in the range of 10.51–18.44 mm via Kirby-Bauer disk diffusion method. 5-Bromo-4-methyl-6-pyrazolylpyrimidine (7e) containing 2-(4-methylpiperazin) substituent showed the best antioxidant and antimicrobial effects. It was effective on all the tested microbial strains except Staphylococcus epidermidis. All the synthesized pyrazolyl pyrimidines, especially (7e) can be used to disinfect the environment and treat infectious diseases.

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An Alternative Regioselective Approach for the Synthesis of Highly Functionalized Derivatives of Pyrazolo[5,1‐b]purine Scaffold

Cited by 18 publications

References 29 publications

Pyrido[1,2-e]purine: Design and Synthesis of Appropriate Inhibitory Candidates against the Main Protease of COVID-19

Pyrido[1,2-e]purine: Design and Synthesis of Appropriate Inhibitory Candidates against the Main Protease of COVID-19

Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents

Synthesis and antimicrobial/antioxidant evaluation of novel pyrimidine-based derivatives with pendant pyrazoles using vinamidinum salts

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