MCR-click synthesis, molecular docking and cytotoxicity evaluation of a new series of indole–triazole–coumarin hybrid peptidomimetics

Pathoor, Rajeena; Bahulayan, D.

doi:10.1039/c8nj00032h

Cited by 26 publications

(11 citation statements)

References 30 publications

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“…Similarly, all molecules were docked against a CDK4 mimic CDK2 protein, in which the CDK2 ATP binding site was substituted with the CDK4 ATP binding pocket (PDB ID: 1GII). [31] Molecular Docking with 2R3J…”

Section: Molecular Dockingmentioning

confidence: 99%

“…The plates were incubated for 24 h at 37 °C. [31] After incubation sterilized Resazurin (67.5 mg powder in 10 mL sterile distilled water) was added to all the wells (10 μl per well) and incubated for 4 h at 37 °C. Color changes were observed and the lowest concentration with no change in color (blue) was recorded as the MIC value.…”

Section: Antibacterial Activitymentioning

confidence: 99%

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Synthesis, Molecular Docking and Evaluation of 1,3,4‐Oxadiazole‐Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents

Nayak

Gaonkar

Hazra

et al. 2022

Chemistry & Biodiversity

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In drug discovery, the hybridization of bioactive pharmacophores is a powerful tool for targeting enzymes involved in cancer and microbial cell growth. A combination of 1,3,4‐oxadiazole and isobenzofuran may improve the antitumor and antimicrobial properties of the hybrid molecules. A series of hybrid molecules having 1,3,4‐oxadiazole and isobenzofuran were synthesized and structural characterization was done by FT‐IR, 1H‐NMR, 13C‐NMR, and mass spectrometry. Molecular docking studies were performed to investigate binding interactions of compounds with proteins (PDB NO: 2R3J and 1GII), and the results were consistent with in vitro anticancer data. All the synthesized compounds were tested for antimicrobial activity against S. aureus, E. faecalis (Gram‐positive) and E. coli and P. aeruginosa (Gram‐negative) bacterial strains. Among the synthesized compounds, 7a and 7b displayed good activity against the tested bacterial strains. Also, compounds were tested for their anti‐tumor activity against breast cancer (MCF‐7) and colon cancer (HCT‐116) cell lines via SRB assay. In comparison to doxorubicin (1.14 μM), hybrids 7e (4.32 μM), 7f (4.15 μM), 7g (4.66 μM), and 7h (4.83 μM) demonstrated comparable IC50 value against the HCT 116 cell line.

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Section: Molecular Dockingmentioning

confidence: 99%

Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis, Molecular Docking and Evaluation of 1,3,4‐Oxadiazole‐Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents

Nayak

Gaonkar

Hazra

et al. 2022

Chemistry & Biodiversity

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“…Among the 1a-f, only 1a was previously reported by Frasinyuk and co-workers. 22 CH 3 ) 3 ), 30.9 (ArC(CH 3 ) 3 ).…”

Section: Synthesis and Characterization Data Of Compounds 22a Synthementioning

confidence: 99%

“…14 Additionally, enzyme inhibitory properties of some benzimidazolium salts were reported. [15][16][17][18] In recent years, many research groups focused on the synthesis and anti-cancer properties of hybrid compounds of coumarin with other bio-active heterocyclic moieties such as pyrimidine, 19 chalcone, 20 βcarboline, 21 indole-triazole, 22 artemisinin, 23 thiazole, 24 and isooxazilones. 25 In the meantime, hybrid compounds of benzimidazole and their anticancer properties were reported with various heterocyclic moieties such as triazine, 26 ellipticine, 27 tetrazine, 28 deoxynucleosides, 29 thiazoles, 30 and chrysin.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic effects of coumarin substituted benzimidazolium salts against human prostate and ovarian cancer cells

et al. 2019

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Coumarin and benzimidazole derivatives have individual biological activities including anticancer. In this study, we aimed to synthesize coumarin-benzimidazole hybrids in order to investigate their anticancer properties. For this purpose, six 6-substituted-4-chloromethylene coumarin derivatives were synthesized. Sixteen coumarin substituted benzimidazolium chlorides were synthesized by the reaction of 4-chloromethylene coumarin and N-benzylbenzimidazole derivatives. All of the synthesized compounds were characterized by 1 H and 13 C NMR, IR spectroscopic techniques and elemental analyses. Cytotoxicities of all compounds were tested by [3-(4,5-dimethylthiazole)-2-yl]-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay against human prostate (PC-3) and ovarian (A2780) cancer cells. All compounds performed significant cytotoxicities at 100 μM against both cancer cell lines. Moreover, some compounds performed significant activities at 1 μM against both cancer cell lines and the obtained results suggest that this type of compounds are promising candidates for the treatment of human prostate and ovarian cancers.

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“…Its overexpression will lead to several types of malignancies such as breast, lung, colorectal, ovarian and pancreatic [ 16 ]. The inhibitors of CDK-2 prompt apoptosis by disrupting the cell cycle and reflect their importance in drug discovery [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Novel 1,2,3-Triazole-Coumarin Hybrid Glycosides and Their Tetrazolyl Analogues: Design, Anticancer Evaluation and Molecular Docking Targeting EGFR, VEGFR-2 and CDK-2

et al. 2022

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This study represents the design and synthesis of a new set of triazole-coumarin-glycosyl hybrids and their tetrazole hybrid analogues possessing various sugar moieties and modified analogues. All the newly synthesized derivatives were screened for their cytotoxic activities against a panel of human cancer cell lines. The coumarin derivatives 10, 13 and 15 derivatives revealed potent cytotoxic activities against Paca-2, Mel-501, PC-3 and A-375 cancer cell lines. These promising analogues were further examined for their inhibitory assessment against EGFR, VEGFR-2 and CDK-2/cyclin A2 kinases. The coumarin-tetrazole 10 displayed broad superior inhibitory activity against all screened enzymes compared with the reference drugs, erlotinib, sorafenib and roscovitine, respectively. The impact of coumarin-tetrazole 10 upon cell cycle and apoptosis induction was determined to detect its mechanism of action. Additionally, it upregulated the levels of casp-3, casp-7 and cytochrome-c proteins and downregulated the PD-1 level. Finally, molecular docking study was simulated to afford better rationalization and gain insight into the binding affinity between the promising derivatives and their targeted enzymes, which could be used as an optimum lead for further modification in the anticancer field.

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MCR-click synthesis, molecular docking and cytotoxicity evaluation of a new series of indole–triazole–coumarin hybrid peptidomimetics

Abstract: The design and synthesis of a new series of indole–triazole-coumarin hybrids as potential CDK2 inhibitors is described.

Cited by 26 publications

References 30 publications

Synthesis, Molecular Docking and Evaluation of 1,3,4‐Oxadiazole‐Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents

Synthesis, Molecular Docking and Evaluation of 1,3,4‐Oxadiazole‐Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents

Cytotoxic effects of coumarin substituted benzimidazolium salts against human prostate and ovarian cancer cells

Novel 1,2,3-Triazole-Coumarin Hybrid Glycosides and Their Tetrazolyl Analogues: Design, Anticancer Evaluation and Molecular Docking Targeting EGFR, VEGFR-2 and CDK-2

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