Design, synthesis, and anti-proliferative evaluation of 1<i>H</i>-1,2,3-triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates in estrogen responsive and triple negative breast cancer cells

Sharma, Bharvi; Gu, Liang; Pillay, Ruvesh Pascal; Cele, Nosipho; Awolade, Paul; Singh, Parvesh; Kaur, Mandeep; Kumar, Vipan

doi:10.1039/d0nj00879f

Cited by 22 publications

(19 citation statements)

References 26 publications

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“…A series of 1H-1,2,3 triazole-grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates was synthesised by Sharma et al. 60 Analysis of SAR revealed that aryl chalcone based conjugates showed better anti-proliferative activities on both the cell lines tested. Among TH β C-chalcone conjugates, the nature of substituent on phenyl ring of chalcone predominantly played an important role in enhancing the cytotoxicity on breast cancer cell lines whereas length of alkyl chain hardly affected the activities.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Derivatives of chalcones-triazole not only exert anti-breast cancer activity 60 , 61 , but also they exhibit activity against multiple types of cancer cells 101 , 102 . A new series of 1,2,3-triazole-chalcone hybrids was synthesised by Ashour and et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Chalcone-triazole derivatives not only possess anticancer activity 60 , 61 , 101 , 102 , but also they exhibit anti-inflammatory activity 114 . Boshra et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Chalcone-triazole derivatives not only possess anticancer activity 60 , 61 , 101 , 102 , anti-inflammatory activity 114 , antibacterial activity 125–127 , and antibacterial activity 134 , but also they exhibit antimalarial activity 143 , 144 . Kant et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

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Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Nature products have been extensively used in the discovery and development of new drugs, as the most important source of drugs. The triazole ring is one of main pharmacophore of the nitrogen-containing heterocycles. Thus, a new class of triazole-containing natural product conjugates has been synthesised. These compounds reportedly exert anticancer, anti-inflammatory, antimicrobial, antiparasitic, antiviral, antioxidant, anti-Alzheimer, and enzyme inhibitory effects. This review summarises the research progress of triazole-containing natural product derivatives involved in medicinal chemistry in the past six years. This review provides insights and perspectives that will help scientists in the fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology.

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Section: Biological Activitiesmentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

“…Chalcone-triazole derivatives not only possess anticancer activity 60 , 61 , 101 , 102 , but also they exhibit anti-inflammatory activity 114 . Boshra et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

See 2 more Smart Citations

Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…They have been shown to interact with various anticancer drug targets, such as DNA (intercalation [3,14,15], groove binding [3,16]), topoisomerase [3,17], kinases [3,18,19], and α-tubulin [3,20]. Several series of β-carboline-triazole hybrids have been synthesized and evaluated for their antiproliferative activity [5]: C3-linked β-carboline-triazole conjugates (an example is shown in Figure 1a) [16], C1-linked β-carboline-triazoles with an aryl-alkyl ether spacer [21], and tetrahydro-β-carboline-chalcone hybrids [22]. .44 µM against HT-29 and HGC-27) [16], (b) coumarin-β-carboline hybrid (GI50 = 67.5 µM against HeLa) [23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Harmirins, Novel Harmine–Coumarin Hybrids as Potential Anticancer Agents

et al. 2021

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As cancer remains one of the major health burdens worldwide, novel agents, due to the development of resistance, are needed. In this work, we designed and synthesized harmirins, which are hybrid compounds comprising harmine and coumarin scaffolds, evaluated their antiproliferative activity, and conducted cell localization and cell cycle analysis experiments. Harmirins were prepared from the corresponding alkynes and azides under mild reaction conditions using Cu(I) catalyzed azide–alkyne cycloaddition, leading to the formation of the 1H-1,2,3-triazole ring. Antiproliferative activity of harmirins was evaluated in vitro against four human cancer cell lines (MCF-7, HCT116, SW620, and HepG2) and one human non-cancer cell line (HEK293T). The most pronounced activities were exerted against MCF-7 and HCT116 cell lines (IC50 in the single-digit micromolar range), while the most selective harmirins were 5b and 12b, substituted at C-3 and O-7 of the β-carboline core and bearing methyl substituent at position 6 of the coumarin ring (SIs > 7.2). Further experiments demonstrated that harmirin 12b is localized exclusively in the cytoplasm. In addition, it induced a strong G1 arrest and reduced the percentage of cells in the S phase, suggesting that it might exert its antiproliferative activity through inhibition of DNA synthesis, rather than DNA damage. In conclusion, harmirin 12b is a novel harmine and coumarin hybrid with significant antiproliferative activity and warrants further evaluation as a potential anticancer agent.

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Design and synthesis of ferrocene‐tethered pyrazolines and pyrazoles: Photophysical studies, protein‐binding behavior with bovine serum albumin, and antiproliferative activity against MDA‐MB‐231 triple negative breast cancer cells

Ghosh

Nayek

Das

et al. 2021

Applied Organom Chemis

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We report synthesis and characterization of a series of ferrocene‐pyrazoline and pyrazole hybrids and demonstrate their biomedical applications. All new compounds were identified with the help of spectroscopic techniques and single‐crystal X‐ray analysis. The compounds from both the series show fluorescent activity. The effect of C5 aryl substituent on the luminescent behavior of the parent system was followed by studying their absorption and emission behavior. The binding affinity of a selected ferrocenyl pyrazoline with C5 2‐naphthyl substituent (4g) to bovine serum albumin (BSA) was examined through fluorescence quenching experiments using excitation wavelength 290 nm. The ligand 4g quenched the intrinsic fluorescence of BSA. Strong binding between 4g and BSA was observed with equilibrium constant for the complex formation of the order of 105 M‐1. In vitro anticancer activity of a series of ferrocenyl‐pyrazolines and pyrazoles (4f, 4g, 4h, 5f, 5g, and 5h) was tested against hormone‐independent triple negative breast cancer cells MDA‐MB‐231 in which maximum inhibition potency was noted for 4h with IC50 value of 3.61 mg ml−1.

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Design, synthesis, and anti-proliferative evaluation of 1H-1,2,3-triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates in estrogen responsive and triple negative breast cancer cells

Abstract:
A series of 1H-1,2,3 triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates were synthesized and in vitro evaluated against estrogen responsive (MCF-7) and triple negative (MDA-MB-231) breast cancer cells.

Cited by 22 publications

References 26 publications

Application of triazoles in the structural modification of natural products

Application of triazoles in the structural modification of natural products

Synthesis and Biological Evaluation of Harmirins, Novel Harmine–Coumarin Hybrids as Potential Anticancer Agents

Design and synthesis of ferrocene‐tethered pyrazolines and pyrazoles: Photophysical studies, protein‐binding behavior with bovine serum albumin, and antiproliferative activity against MDA‐MB‐231 triple negative breast cancer cells

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Design, synthesis, and anti-proliferative evaluation of 1H-1,2,3-triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates in estrogen responsive and triple negative breast cancer cells

Abstract: A series of 1H-1,2,3 triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates were synthesized and in vitro evaluated against estrogen responsive (MCF-7) and triple negative (MDA-MB-231) breast cancer cells.

Cited by 22 publications

References 26 publications

Application of triazoles in the structural modification of natural products

Application of triazoles in the structural modification of natural products

Synthesis and Biological Evaluation of Harmirins, Novel Harmine–Coumarin Hybrids as Potential Anticancer Agents

Design and synthesis of ferrocene‐tethered pyrazolines and pyrazoles: Photophysical studies, protein‐binding behavior with bovine serum albumin, and antiproliferative activity against MDA‐MB‐231 triple negative breast cancer cells

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Abstract:
A series of 1H-1,2,3 triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates were synthesized and in vitro evaluated against estrogen responsive (MCF-7) and triple negative (MDA-MB-231) breast cancer cells.