Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents

Ashok, D.; Thara, Gugulothu; Kumar, Bhukya Kiran; Gadipelli, Srinivas; Dharavath, Ravinder; Thumma, Vishnu; Sarasija, M.; Bujji, Sushmitha

doi:10.1039/d2ra05960f

Cited by 19 publications

(15 citation statements)

References 52 publications

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“…Initially, water molecules of protein were removed, and polar hydrogens were added. [47] The ligands were sketched by using Chemdraw Professional 16.0 (www.acdlabs.com) in MDL file. The PDB files of both target and ligand molecules were loaded into PyRx tool.…”

Section: Molecular Dockingmentioning

confidence: 99%

New Imidazo[4,5‐c]pyridine‐piperidine Hybrids as Potential Anti‐cancer Agents and In‐Silico Studies

Rejinthala,

Endoori,

Thumma

et al. 2024

ChemistrySelect

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Design and synthesis of a series of novel hybrid molecules that combine Imidazo[4,5‐c] pyridines with piperdines are presented in this paper. Total 17 derivatives were meticulously synthesized and characterized using 1H NMR, 13C NMR, MS and elemental analysis techniques. The in vitroanticancer activities are estimated by verifying their effectiveness against the MCF‐7 human breast adenocarcinoma and A549 lung cancer cell line, with cisplatin and doxorubicin serving as reference drugs. Several of these compounds demonstrated significant potential, displaying IC50 values within the range of 12.26–84.5 μM for A549, and 13.37–69.82 μM for MCF‐7. Notably, compound 11 bis found to be more potent than the standard drug cisplatin with an IC50 of 12.26±0.8 μM against A549 cells, while compound 11 d exhibited highest inhibition with an IC50 of 13.37±0.4 μM against MCF‐7 cells. Although its effectiveness was moderately lower when compared to doxorubicin, it still retained substantial anticancer activity. Molecular docking studies were performed to decouple the binding affinity and ligand interactions of the compounds with the estrogen receptor alpha (ERα) (PDB ID: 3ERT). The pharmacokinetic evaluation revealed favourable drug‐likeness properties for all the molecules, suggesting their potential as therapeutic agents.

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Section: Molecular Dockingmentioning

confidence: 99%

New Imidazo[4,5‐c]pyridine‐piperidine Hybrids as Potential Anti‐cancer Agents and In‐Silico Studies

Rejinthala,

Endoori,

Thumma

et al. 2024

ChemistrySelect

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“…The indole derivatives 66 were obtained by a three-step synthetic route beginning with the N-alkylation of tetrahydro-1 H -carbazoles, followed by copper-catalyzed Huisgen [3 + 2] cycloaddition reaction with aromatic azides 65 in the presence of CuSO 4 and sodium ascorbate in DMF-H 2 O (2:1) for 6 min under microwave irradiation (Scheme ). Among the synthesized compounds, 66b , 66d , and 66e were found to exhibit good antioxidant, anticancer, and antimicrobial activities …”

Section: Synthesis Of Cu-catalyzed Heterocyclic Moieties Via Microwav...mentioning

confidence: 99%

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

Jena

Chanda

2023

ACS Omega

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Heterocyclic moieties play a significant role in the field of drug discovery. C−N and C−O bond formation reactions are the primary synthetic sequence for the generation of heterocyclic molecules. The generation of C−N and C−O bonds involves the use of mostly Pd or Cu catalysts although other transition metal catalyst's are also involved. However, in C−N and C−O bond formation reactions, several problems were faced such as catalytic systems containing costly ligands, lack of substrate scope, lots of waste generation, and high temperature conditions. So it is imperative to uncover new eco-friendly synthetic strategies. In view of enormous drawbacks, it is important to develop an alternate microwave-assisted synthesis of heterocycles via C−N and C−O bond formation, which provides a short reaction time, tolerance for functional groups, and less waste production. Numerous chemical reactions have been accelerated using microwave irradiation which provides a cleaner reaction profile, lower energy consumption, and higher yields. This review article highlights a comprehensive overview on the potential application of microwave assisted synthetic routes for the synthesis of diverse heterocycles via mechanistic pathways covering the year ranges from 2014 to 2023, along with possible biological interests.

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“…Molecular docking is a rapidly growing platform in Computer Aided Drug Discovery and Design (CADDD) [31] . Autodock Vina integrated PyRx is an open‐source virtual screening tool most widely used for in silco studies [32–36] …”

Section: Introductionmentioning

confidence: 99%

“…[31] Autodock Vina integrated PyRx is an open-source virtual screening tool most widely used for in silco studies. [32][33][34][35][36] However, additional attempts are still required to improve the remedial use of these drugs to complete healing of breast cancer. Moreover, Feng Gao and co-authors have elucidated that 1,2,3-triazole-containing compounds were working as good anti-lung cancer agents and clearly explained their mechanism in the treatment of lung cancer development as a novel antilung cancer agent with new technology with low toxicity and high efficacy.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Cytotoxicity of New Coumarin‐1,2,3‐triazole Derivatives: Evaluation of Anticancer Activity and Molecular Docking Studies

Premsagar Miriyala,

Raj Thommandru,

Kashanna

et al. 2023

Chemistry & Biodiversity

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A library of new coumarin-1,2,3-triazole hybrids 7a-l were synthesized from 4-(diethylamino)-2-hydroxybenzaldehyde precursor through a series of reactions including Vilsmeier-Haack reaction and condensation reaction to achieve key intermediate oxime and further performed click reaction by using different aromatic azides. We screened all molecules in silico against crystal structure of Serine/threonine-protein kinase 24 (MST3), based on these results all molecules were screened for their cytotoxicity against human breast cancer MCF-7 and lung cancer A-549 cell lines. Compound 7 b (p-bromo) showed best activity against both cell lines MCF-7 and A-549 with IC 50 value of 29.32 and 21.03 μM, respectively, in comparison to Doxorubicin corresponding IC 50 value of 28.76 and 20.82 μM. Another compound 7 f (o-methoxy) also indicated good activity against both cell lines with IC 50 value of 29.26 and 22.41 μM. The toxicity of all compounds tested against normal HEK-293 cell lines have not shown any adverse effects.

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Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents

Abstract: Easy and approachable synthesis. Conventional and microwave irradiational methods. 21 examples. In vitro antimicrobial, antioxidant and anticancer activities. Molecular docking studies.

Cited by 19 publications

References 52 publications

New Imidazo[4,5‐c]pyridine‐piperidine Hybrids as Potential Anti‐cancer Agents and In‐Silico Studies

New Imidazo[4,5‐c]pyridine‐piperidine Hybrids as Potential Anti‐cancer Agents and In‐Silico Studies

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

Design, Synthesis and Cytotoxicity of New Coumarin‐1,2,3‐triazole Derivatives: Evaluation of Anticancer Activity and Molecular Docking Studies

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