Synthesis and Biological Evaluation of 1,2,3‐triazole tethered Pyrazoline and Chalcone Derivatives

Hussaini, S.M. Ali; Poornachandra, Y.; Babu, K. Suresh; Shaik, Thokhir Basha; Kumar, C. Ganesh; Kamal, Ähmed

doi:10.1111/cbdd.12738

Cited by 40 publications

(16 citation statements)

References 29 publications

(40 reference statements)

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“…Compound 66 ( Figure 24 ) inhibited HepG 2 cell line most effectively (GI 50 = 6.7 μM) and displayed consistent inhibitory effect on the other three cell lines tested (GI 50 < 10 μM for HeLa, DU145 and A549) among 16 analogues with combretastatin-A4 alike substituents conjugated with triazole [ 148 ]. Moreover, it caused accumulation of cells in G 2 /M phase and inhibited tubulin polymerization (36% inhibition at 3 μM).…”

Section: 2-pyrazolinesmentioning

confidence: 96%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

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Pyrazolines are five-membered heterocycles possessing two adjacent nitrogens. They have attracted significant attention from organic and medicinal chemists due to their potent biological activities and the numerous possibilities for structural diversification. In the last decade, they have been intensively studied as targets for potential anticancer therapeutics, producing a steady yearly rise in the number of published research articles. Many pyrazoline derivatives have shown remarkable cytotoxic activities in the form of heterocyclic or non-heterocyclic based hybrids, such as with coumarins, triazoles, and steroids. The enormous amount of related literature in the last 5 years prompted us to collect all these published data from screening against cancer cell lines, or protein targets like EGFR and structure activity relationship studies. Therefore, in the present review, a comprehensive account of the compounds containing the pyrazoline nucleus will be provided. The chemical groups and the structural modifications responsible for the activity will be highlighted. Moreover, emphasis will be given on recent examples from the literature and on the work of research groups that have played a key role in the development of this field.

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Section: 2-pyrazolinesmentioning

confidence: 96%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

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“…Both of them have shown their potential as novel anticancer candidates. Hussaini et al synthesized a series of chalcone-1,2,3-triazole hybrids ( 36 , GI 50 : 1.3–186.2 µM) with the same substituents as combretastatin-A4, which can lead to the accumulation of A549, HeLa, DU145, and HepG2 cancer cell lines in the G2/M phase, inhibit tubulin polymerization, and trigger apoptosis by inducing changes to the mitochondrial membrane potential and activating caspases 3 and 9 [ 77 ]. Moreover, Ahmed et al prepared a series of novel 1,2,4-triazole/chalcone hybrids ( 37 , IC 50 : 4.4–16.04 µM) that can induce the apoptosis of human lung adenocarcinoma A549 cells through a caspase-3-dependent pathway [ 78 ].…”

Section: Strategies Employed To Produce Anticancer Chalconesmentioning

confidence: 99%

Chalcone Derivatives: Role in Anticancer Therapy

et al. 2021

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Chalcones (1,3-diaryl-2-propen-1-ones) are precursors for flavonoids and isoflavonoids, which are common simple chemical scaffolds found in many naturally occurring compounds. Many chalcone derivatives were also prepared due to their convenient synthesis. Chalcones as weandhetic analogues have attracted much interest due to their broad biological activities with clinical potentials against various diseases, particularly for antitumor activity. The chalcone family has demonstrated potential in vitro and in vivo activity against cancers via multiple mechanisms, including cell cycle disruption, autophagy regulation, apoptosis induction, and immunomodulatory and inflammatory mediators. It represents a promising strategy to develop chalcones as novel anticancer agents. In addition, the combination of chalcones and other therapies is expected to be an effective way to improve anticancer therapeutic efficacy. However, despite the encouraging results for their response to cancers observed in clinical studies, a full description of toxicity is required for their clinical use as safe drugs for the treatment of cancer. In this review, we will summarize the recent advances of the chalcone family as potential anticancer agents and the mechanisms of action. Besides, future applications and scope of the chalcone family toward the treatment and prevention of cancer are brought out.

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“…Compounds 8 (IC 50 : 9-60 μm, MTT assay) are active against A549 cells, and a mechanistic study revealed that these compounds could exert antiproliferative activity by inducing apoptosis and G2/S arrest as well as triggering mitochondrial potential loss (Yadav et al, 2017). An SAR study demonstrated that introducing a methoxy group into the phenyl ring could not increase the activity apparently, and the activity of compounds 9 (GI 50 : 4.7-11.9 μm, SRB assay) is considerably inferior to that of combretastatin-A4 (GI 50 : 0.08 μm) against A549 cells (Hussaini et al, 2016). Further study proved that the benzyl group at the N-1 position of the 1,2,3-triazole moiety is not crucial for the activity, and replacement by the phenyl ring is also permitted, as evidenced by that compounds 10a,b (IC 50 : 62.51 and 75.41 μm, MTT assay) show comparable activity to doxorubicin (IC 50 : 39.86 μm) against A549 cells (Raghavender et al, 2020 (Chinthala et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

1,2,3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship

Liang

Sun

et al. 2021

Front. Pharmacol.

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Lung cancer is the most common malignancy and leads to around one-quarter of all cancer deaths. Great advances have been achieved in the treatment of lung cancer with novel anticancer agents and improved technology. However, morbidity and mortality rates remain extremely high, calling for an urgent need to develop novel anti–lung cancer agents. 1,2,3-Triazole could be readily interact with diverse enzymes and receptors in organisms through weak interaction. 1,2,3-Triazole can not only be acted as a linker to tether different pharmacophores but also serve as a pharmacophore. This review aims to summarize the recent advances in 1,2,3-triazole–containing compounds with anti–lung cancer potential, and their structure–activity relationship (SAR) together with mechanisms of action is also discussed to pave the way for the further rational development of novel anti–lung cancer candidates.

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Synthesis and Biological Evaluation of 1,2,3‐triazole tethered Pyrazoline and Chalcone Derivatives

Cited by 40 publications

References 29 publications

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Chalcone Derivatives: Role in Anticancer Therapy

1,2,3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship

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