Synthesis and in vitro anticancer activity of 4H-pyrano[2,3-d]pyrimidine−1H-1,2,3-triazole hybrid compounds bearing D-glucose moiety with dual EGFR/HER2 inhibitory activity and induced fit docking study

Hai, Do Son; Huyen, Le Thi; Thành, Nguyễn Đình; Ha, Nguyen Thi Thu; Tung, Do Tien; Le, Cao Thi; Van, Hoàng Thi Kim; Toan, Vu Ngoc

doi:10.1016/j.molstruc.2022.133932

Cited by 13 publications

(8 citation statements)

References 37 publications

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“…Yields of substituted ethyl 4 H -pyran-3-carboxylates were 63–75% (Table S2 in the ESI†). 33 Reaction of these ethyl esters with acetic anhydride in the presence of trifluoroacetic acid (TFA) as catalyst under reflux at 100 °C for 15 min led to the production of 4 H -pyrano[2,3- d ]pyrimidines 7a–g and 8a–g , respectively (Scheme 2). 34 These compounds were formed with yields of 69–78% (Table S3 in the ESI†).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and inhibitory activity against MurA and MurZ enzymes of 4H-pyrano[2,3-d]pyrimidine–1H-1,2,3-triazole hybrid compounds having piperidine and morpholine rings

Thành

Hai

et al. 2023

New J. Chem.

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Section: Resultsmentioning

confidence: 99%

Synthesis and inhibitory activity against MurA and MurZ enzymes of 4H-pyrano[2,3-d]pyrimidine–1H-1,2,3-triazole hybrid compounds having piperidine and morpholine rings

Thành

Hai

et al. 2023

New J. Chem.

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“…Thanh and co-workers synthesized a series of 36 derivatives of 4H-pyrano[2,3-d]pyrimidine 515a-zj by click cycloaddition reaction of polysubstituted 4H-pyrano[2,3-d]pyrimidines 514azj 167 containing propargyl group on nitrogen atom with peracetylated D-glucopyaranosyl azide 7 by using ultrasound, CuNPs@Montmorillonite as a catalyst and DIPEA in the presence of t BuOH/H2O at 25°C (Scheme 51). 168 Scheme 51 Synthesis of compounds 515a-zj All the synthesized compounds 515a-zj were tested against five typical human cancer cell lines, including breast adenocarcinoma cells MCF-7, hepatocellular carcinoma cells HepG2 and cervical cancer cells HeLa by using three reference drugs-Doxorubicin (DOX), Lapatinib, and Erlotinib then it was found that Some compounds, such as 515v, 515x, 515z, 515zc, 515zf, and 515zg against MCF-7, 515s, 515t, 515w, 515zh and 515zi against HepG2, and 515h, 515j, 515zf, and 515zh against HeLa cancer cell lines, demonstrated excellent activity against tested cancer cell lines with IC50 < 4 μM. In comparison to lapatinib, compounds 8v, 8z, 8zc, and 8zf significantly inhibited the activity of EGFR and HER2 tyrosine kinases.…”

Section: Template For Synopen Thiemementioning

confidence: 99%

Recent Advances in the Synthesis of Bioactive Glycohybrids via Click-Chemistry

Singh

Tyagi

Mishra

et al. 2023

SynOpen

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Carbohydrates, traditionally known for their energy-providing role, have gained significant attention in drug discovery due to their diverse bioactivities and stereodiversity. However, pure carbohydrate molecules often exhibit limited bioactivity and suboptimal chemical and physical characteristics. To address these challenges, functional groups with bioactive scaffolds have been incorporated into carbohydrate to enhance their bioactivity and improve their overall properties. Among the various synthetic methods available, click chemistry has emerged as a powerful tool for the synthesis of carbohydrate-containing bioactive scaffolds, known as glycohybrids. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification and compatibility with multiple functional groups. In the present review, we have emphasized the recent advances and most pertinent research on the development of 1,2,3-triazole-containing glycohybrids using click reaction, their biological evaluations and the structure-activity relationship during 2017-2023. These newly synthesised glycohybrids could potentially be developed as new chemical entities (NCE) in pharmaceutical chemistry and may encourage the use of carbohydrates in drug discovery processes. 1 Introduction 2 CuAAC click chemistry mediated synthesis of triazole based glycohybrids and their biological activities 3 Conclusions and perspective

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“…It has been reported in previous studies that the active site of the targeted receptor was mainly composed of residues Phe699, Gly700, Lys721, Met769, Arg817, Thr830, and Asp831. 35,36 The hydrophobic pockets formed with compound 21g are revealed in Figure 3, involving residues Leu694, Val702, Alaa719, Leu768, and Leu820. The interaction is further strengthened through two conventional hydrogen bonds with Lys721 and Met769.…”

Section: Docking Studiesmentioning

confidence: 99%

Dihydroartemisinin and zerumbone esters of ataluren and its analogs as anticancer agents and EGFR inhibitors

Tran,

Truong,

Nguyen

et al. 2023

Journal of Chemical Research

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In a five-step procedure, 18 new esters (20a–i and 21a–i) of ataluren and its analogs with dihydroartemisinin and zerumbone were synthesized from methyl 3-cyanobenzoate. The screening for their cytotoxic activity against two cancer cell lines, HepG2 and MCF-7, showed that most esters exhibit activity against the tested cell lines, with IC50 values in the range of 1.61–36.52 µM. Among the tested compounds, ester 21f containing 4-methoxy in structure R did not show cytotoxic activity. The interactions of these new derivatives with the epidermal growth factor receptor protein were also investigated by molecular docking studies. The obtained binding conformation revealed several notable results, demonstrating similarities between molecular modeling theory and experiment. These results contributed to interpreting the in vitro cytotoxicity of esters and proposed the basis for predicting the mechanism of their cytotoxic action.

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Synthesis and in vitro anticancer activity of 4H-pyrano[2,3-d]pyrimidine−1H-1,2,3-triazole hybrid compounds bearing D-glucose moiety with dual EGFR/HER2 inhibitory activity and induced fit docking study

Cited by 13 publications

References 37 publications

Synthesis and inhibitory activity against MurA and MurZ enzymes of 4H-pyrano[2,3-d]pyrimidine–1H-1,2,3-triazole hybrid compounds having piperidine and morpholine rings

Synthesis and inhibitory activity against MurA and MurZ enzymes of 4H-pyrano[2,3-d]pyrimidine–1H-1,2,3-triazole hybrid compounds having piperidine and morpholine rings

Recent Advances in the Synthesis of Bioactive Glycohybrids via Click-Chemistry

Dihydroartemisinin and zerumbone esters of ataluren and its analogs as anticancer agents and EGFR inhibitors

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