A facile one‐pot regioselective synthesis of [1,2,4]triazolo[4,3‐<i>a</i>]5(1<i>H</i>)‐pyrimidinones via tandem Japp–Klingemann, Smiles rearrangement, and cyclization reactions

Shawali, Ahmad S.; Abdallah, Magda A.; Mosselhi, Mosselhi A. N.; Farghaly, Thoraya A.

doi:10.1002/hc.10008

Cited by 31 publications

(14 citation statements)

References 30 publications

(12 reference statements)

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“…To verify the assigned structure of the products 3a – c , we have synthesized these compounds by alternative methods. Thus, treatment of aminothiouracil ( 4 ) with 2-[2-(4-methyl-2- phenylthiazole-5-carbonyl) hydrazono]- N -arylpropanehydrazonoyl chlorides ( 5a – c ) [ 37 ] in dioxane, in the presence of a catalytic amount of triethylamine, under thermal conditions, gave the authentic products identical in all respects (mp, mixed mp, IR) with the isolated products 3a – c via Smiles rearrangement [ 38 ] and elimination of H 2 S ( Scheme 2 ).…”

Section: Resultsmentioning

confidence: 99%

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)

et al. 2020

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A novel series of some hydrazones bearing thiazole moiety were generated via solvent-drop grinding of thiazole carbohydrazide 2 with various carbonyl compounds. Also, dehydrative-cyclocondensation of 2 with active methylene compounds or anhydrides gave the respective pyarzole or pyrazine derivatives. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses. Additionally, the anti-viral activity of all the products was tested against SARS-CoV-2 main protease (Mpro) using molecular docking combined with molecular dynamics simulation (MDS). The average binding affinities of the compounds 3a, 3b, and 3c (–8.1 ± 0.33 kcal/mol, –8.0 ± 0.35 kcal/mol, and –8.2 ± 0.21 kcal/mol, respectively) are better than that of the positive control Nelfinavir (–6.9 ± 0.51 kcal/mol). This shows the possibility of these three compounds to effectively bind to SARS-CoV-2 Mpro and hence, contradict the virus lifecycle.

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Section: Resultsmentioning

confidence: 99%

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)

et al. 2020

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“…From our expertise in the field of synthesis triazolopyrimidines, [20][21][22][23][24][25] we interested here in to synthesis new derivatives of triazolopyrimidines from the reaction of thione 10 with hydrazonoyl chlorides 20. Thus, this reaction carried out in dioaxane in the presence of Et 3 N thermally or using MW irradiations to afford triazolopyrimidines 23a-e (Scheme 5 and Table 1).…”

Section: Resultsmentioning

confidence: 99%

New azoloazine derivatives as antimicrobial agents: Synthesis under microwave irradiations, structure elucidation, and antimicrobial activity

Kassem

Abbas

Al‐Qurashi

et al. 2019

Journal of Heterocyclic Chem

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With aiding of microwave radiation, new series of fused-thiazolopyrimidines and fused-triazolopyrimidines each with cycloheptane have been synthesized through the reaction of cycloheptane-thione with α-haloketones or hydrazonoyl chlorides in short-time intervals as well as high yield. Moreover, reaction of 2,7-bis(2-chlorobenzylidene)cycloheptan-1-one with o-aminothiophenol and heterocyclic amines afforded benzo[b]cyclohepta[e][1,4]thiazepine derivative and cycloheptapyrimidines fused with different azoles, respectively. The structure for all products was discussed and proved based on the results of spectral data and elemental analysis. Evaluation of the antimicrobial activity of selected products indicated that most of derivatives showed their potent activity exceeds the reference antibiotic in some cases.

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“…There are several reports on the preparation of pyrimidinethiones and pyrimidine-ones derivatives using several reagents such as 3-isothiocyanato-propene [19], oxalyl chloride [20], cyanothioacetamide [21], formaldehyde [22], furoyl chloride [23], and diazotized anilines [24]; however, some of these reagents require condition specials. In this study, the first stage involved the preparation of a pyrimidine-thione using the three-component system (α-naphthol, benzaldehyde, and thiourea) in mild conditions (Fig.…”

Section: Results and Discussion Evaluation Chemistrymentioning

confidence: 99%

Design and synthesis of a new steroid-macrocyclic derivative with biological activity

et al. 2017

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The aims of this study were to evaluate the positive inotropic effect of a new macrocyclic derivative (compound 11) and characterize the molecular mechanism involved in its biological activity. The first step was achieved by synthesis of a macrocyclic derivative involving a series of reactions for the preparation of several steroid derivatives such as (a) steroidpyrimidinone (3 and 4), (b) steroid-amino (5), (c) steroidimino (6), (d) ester-steroid (7 and 8), and (e) amido-steroid (9 and 10). Finally, 11 was prepared by removing the tertbutyldimethylsilane fragment of 10. The biological activity of compounds on perfusion pressure and vascular resistance was evaluated on isolated rat heart using the Langendorff model. The inotropic activity of 11 was evaluated in presence of prazosin, metoprolol, indomethacin, nifedipine, and flutamide to characterize its molecular mechanism. Theoretical experiments were carried out with a Docking model, to assess potential interactions of androgen receptor with 11. The results showed that only this macrocyclic derivative exerts changes on perfusion pressure and vascular resistance translated as the positive inotropic effect, and this effect was blocked with flutamide; these data indicate that the positive inotropic activity induced by this macrocyclic derivative was via androgen receptor activation. The theoretical results indicated that the interaction of the macrocyclic derivative with the androgen receptor involves several amino acid residues such as Leu 704 , Asn 705 , Met 780 , Cys 784 , Met 749 , Leu 762 , Phe 764 , Ser 778 , and Met 787 . In conclusion, all these data suggest that the positive inotropic activity of the macrocyclic derivative may depend on its chemical structure.

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A facile one‐pot regioselective synthesis of [1,2,4]triazolo[4,3‐a]5(1H)‐pyrimidinones via tandem Japp–Klingemann, Smiles rearrangement, and cyclization reactions

Cited by 31 publications

References 30 publications

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)

New azoloazine derivatives as antimicrobial agents: Synthesis under microwave irradiations, structure elucidation, and antimicrobial activity

Design and synthesis of a new steroid-macrocyclic derivative with biological activity

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