Synthesis and antiviral activity of 1,2,3-triazole glycosides based substituted pyridine via click cycloaddition

El‐Sayed, Wael A.; Khalaf, Hemat S.; Mohamed, S.A.; Hussien, Hadeel A.K; Kutkat, Omnia; Amr, Abd El‐Galil E.

doi:10.1134/s1070363217100279

Cited by 57 publications

(22 citation statements)

References 32 publications

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“…The particular 1 H-NMR spectra revealed the signal attributed to anomeric hydrogen of the glycosyl unit as doublet at δ 5.20–5.55 ppm, exhibiting coupling constants in the range 9.4–9.8 Hz indicating the β-type orientation of the thioglycosidic attachment. For the compounds possessing β- N -glycosidic part near to the C=S group, the anomeric proton has been reported to be exist [34,35,36] at higher chemical shifts (δ 6.5–7.2 ppm). Such relatively raised δ values in such type of structures are explained by the anisotropic deshielding influence of the C=S.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of New 1,3,4-Thiadiazole Thioglycosides and 1,2,3-Triazolyl-1,3,4-Thiadiazole N-glycosides

et al. 2019

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New 1,3,4-thiadiazole thioglycosides linked to substituted arylidine systems were synthesized via glycosylation of the prepared 1,3,4-thiadiazole thiol compounds. Click strategy was also used for the synthesis of new 1,3,4-thiadiazole and 1,2,3-triazole hybrid glycosides by reaction of the acetylenic derivatives with different glycosyl azids followed by deacetylation process. The cytotoxic activities of the prepared compounds were studied against HCT-116 (human colorectal carcinoma) and MCF-7 (human breast adenocarcinoma) cell lines using the MTT assay. The results showed that the key thiadiazolethione compounds 2 and 3, the triazole glycosides linked to p-methoxyarylidine derivatives 14 and 15 in addition to the free hydroxyl glycoside 20 were found potent in activity comparable to the reference drug doxorubicin against MCF-7 human cancer cells. The acetylenic derivative 2 and glycoside 20 were also found highly active against HCT-116 cell lines.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of New 1,3,4-Thiadiazole Thioglycosides and 1,2,3-Triazolyl-1,3,4-Thiadiazole N-glycosides

et al. 2019

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“…The chemical shift values as well as the coupling constants of the anomeric protons J 1′,2′ = 9.8 Hz indicated the thio ‐glycosidic linkage with β ‐conformation of the sugar moiety, which was in full agreement with the assigned structures. The thio‐linkage of the sugar moiety with the heterocyclic base was also supported by the value of the anomeric proton as this value would be at higher chemical shift in N ‐glycosides . The 13 C NMR spectrum of compound 16 also confirmed the β ‐conformation of the sugar with the base (cf.…”

Section: Resultsmentioning

confidence: 75%

Design, Synthesis, and Anticancer Activity of New Oxadiazolyl‐Linked and Thiazolyl‐Linked Benzimidazole Arylidines, Thioglycoside, and Acyclic Analogs

Nassar

kady

Awad

et al. 2019

Journal of Heterocyclic Chem

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2‐[(4‐Thiazolylmethyl)thio]‐1H‐benzimidazole 3 was prepared and was allowed to react with ethyl chloroactate then with hydrazine hydrate to afford the hydrazide derivative 5, which was then reacted with aromatic aldehydes to afford the corresponding arylidine derivatives 6–9. Heterocyclization of the latter hydrazones with acetic anhydride afforded the substituted 1,3,4‐oxadiazoline derivatives 10–13. In addition, new ((thiazolyl)imidazolyl) oxadiazole thioglycoside and acyclic‐C nucleoside analog were prepared via heterocylization of the hydrazide 5 then glycosylation with α‐acetobromoglucose or condensation with D‐xylose, respectively. All the new compounds were structurally characterized. The anticancer activity of some of the newly synthesized compounds was studied against human breast cancer cells (MCF‐7). The results of the anticancer activity showed that compounds 8, 11, 12, 17, and 18 revealed high activities superior to Doxorubicin; however, the other derivatives showed moderate to low inhibition activities against human breast cancer cells. Docking studies into CDK2 enzyme were investigated, which supported the anticancer activity results.

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“…For this purpose, a combination of different active components of a molecule can be employed through which each drug moiety is designed to bind independently to different biological targets and synchronously accumulate at both target sites (1). Among different classes of nitrogen-containing heterocyclic compounds, quinoxaline and triazolo are well known for their broad antibacterial (2,3), antifungal (4,5), anti-mycobacterial (6,7), antiviral (8,9), anti-inflammatory (10,11), anticancer (12,13) and antimalarial (14,15) properties. In our previous study, we synthesized 3substituted 5H-(1,2,4)triazolo(3',4':2,3) (1,3,4)thiadiazino(5,6-b)quinoxaline derivatives under solvent-free conditions (16).…”

Section: Introductionmentioning

confidence: 99%

In Vitro Antimicrobial Activity of New 3-Substituted 5H-(1,2,4)Triazolo(3',4':2,3) (1,3,4)Thiadiazino(5,6-B)Quinoxaline Derivatives

et al. 2020

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Background and objectives: Antimicrobial resistance is a serious threat to global public health. The overuse and misuse of antibiotics are the most important contributing factors to development of antibiotic resistance. Thus, there is an urgent need to identify and discover new compounds against drug-resistant microorganisms. We have previously synthesized new series of 3-substituted 5H-(1,2,4)triazolo(3',4':2,3) (1,3,4)thiadiazino(5,6-b)quinoxaline derivatives (4a-4f). Here, we evaluate the antimicrobial activity of these derivatives against methicillin-resistant Staphylococcus aureus, S. aureus, Streptococcus pyogenes, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, Candida tropicalis and Candida krusei. Methods: The agar well diffusion and agar dilution methods were used for determining inhibition zone diameter and minimum inhibitory concentration during preliminary evaluation of antimicrobial activity. Results: All synthesized compounds exhibited antibacterial and antifungal activity against the tested microorganisms. Conclusion: Our findings indicate the antimicrobial potential of the six novel synthetic triazolo thiadiazin quinoxaline compounds.

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Synthesis and antiviral activity of 1,2,3-triazole glycosides based substituted pyridine via click cycloaddition

Cited by 57 publications

References 32 publications

Synthesis and Cytotoxic Activity of New 1,3,4-Thiadiazole Thioglycosides and 1,2,3-Triazolyl-1,3,4-Thiadiazole N-glycosides

Synthesis and Cytotoxic Activity of New 1,3,4-Thiadiazole Thioglycosides and 1,2,3-Triazolyl-1,3,4-Thiadiazole N-glycosides

Design, Synthesis, and Anticancer Activity of New Oxadiazolyl‐Linked and Thiazolyl‐Linked Benzimidazole Arylidines, Thioglycoside, and Acyclic Analogs

In Vitro Antimicrobial Activity of New 3-Substituted 5H-(1,2,4)Triazolo(3',4':2,3) (1,3,4)Thiadiazino(5,6-B)Quinoxaline Derivatives

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