1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships

Xu, Zhi; Zhao, Shijia; Liu, Yi

doi:10.1016/j.ejmech.2019.111700

Cited by 379 publications

(190 citation statements)

References 328 publications

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“…In detail, this nitrogen-based heterocycle, obtained through the copper-catalyzed Huisgen 1,3-dipolar cycloaddition, could indeed represent a "privileged" fragment for drug discovery purposes, as it is expected to perform non-covalent interactions with a number of selected targets, offering an opportunity to obtain lead compounds endowed with an enriched efficacy profile. Certainly, this strategy has been largely exploited for the design of lead compounds for therapeutic applications among which the anticancer agents [23,24]. It has been acknowledged that design strategies based on "privileged sub-substructures" combination are a powerful tool to generate promising lead compounds [25].…”

Section: Introductionmentioning

confidence: 99%

Curcumin-1,2,3-Triazole Conjugation for Targeting the Cancer Apoptosis Machinery

et al. 2020

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The burden of neoplastic diseases is widely recognized as a severe cause of mortality. The clinical inadequacy of most anticancer therapeutics urgently prompted intense drug discovery efforts toward the identification of new chemical entities endowed with a potent and safe antitumor profile. In this scenario, targeting cancer cells apoptosis machinery has emerged as a relevant strategy, useful for tackling the emergence of drug resistance. On this basis, a small library of naturally inspired hybrid molecules was obtained by combining, through a click chemistry approach, “privileged” synthons such as curcumin scaffold and 1,2,3-triazole building block. Compound 1, bearing a para-fluoro phenyl moiety, showed low-micromolar potency against T acute lymphoblastic leukemia cell growth. More in-depth biologic studies demonstrated, for this analog, cell death-inducing properties associated with its capability to simultaneously activate both the receptor and the mitochondrial apoptosis cascades. This peculiar behavior offers promises for achieving an expanded anticancer effect, namely intense cytotoxic response coupled with reduced predisposition of chemoresistance insurgence. Altogether, this study allowed the identification of compound 1 as a lead compound worth to be progressed as an anticancer drug candidate.

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Section: Introductionmentioning

confidence: 99%

Curcumin-1,2,3-Triazole Conjugation for Targeting the Cancer Apoptosis Machinery

et al. 2020

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“…great attention due to their extensive biological properties such as antioxidant, [5] antifungal, [6,7] antitubercular, [8] antibacterial, [9] anticancer, [10] anti-HIV, [11] antimicrobial, [12] and antimalarial activity. [13] The 1,4-disubstituted-1,2,3-triazoles were synthesized via coppercatalyzed azide-alkyne cycloaddition reaction, well known as a click chemistry reaction.…”

Section: Diversely Functionalized 123-triazole Derivatives Have Attmentioning

confidence: 99%

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

Akolkar

Nagargoje

Shaikh

et al. 2020

Archiv der Pharmazie

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A series of new 1,2,3-triazole-tethered coumarin conjugates linked by N-phenylacetamide was efficiently synthesized via the click chemistry approach in excellent yields. The synthesized conjugates were evaluated for their in vitro antifungal and antioxidant activities. Antifungal activity determination was carried out against fungal strains such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger and Cryptococcus neoformans. Compounds 7b, 7d, 7e, 8b and 8e displayed higher potency than the standard drug miconazole, with lower minimum inhibitory concentration values. Also, compound 7a exhibited potential radical scavenging activity as compared with the standard antioxidant butylated hydroxytoluene. In addition, a molecular docking study of the newly synthesized compounds was carried out, and the results showed a good binding mode at the active site of the fungal (C. albicans) P450 cytochrome lanosterol 14α-demethylase enzyme. Furthermore, the synthesized compounds were also tested for ADME properties, and they demonstrated potential as good candidates for oral drugs.

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“…1,2,3-Triazoles are important heterocycles due to their immense pharmacological and biological applications [5][6][7]. In addition, compounds containing pyrazoles and thiazole a Occupancy: 0.5.…”

Section: Commentmentioning

confidence: 99%

The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C₃₀H₂₅FN₁₀S⋅C₃H₇NO

Alotaibi

Abdel‐Wahab

Hegazy

et al. 2020

Zeitschrift Für Kristallographie - New Crystal Structures

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1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships

Cited by 379 publications

References 328 publications

Curcumin-1,2,3-Triazole Conjugation for Targeting the Cancer Apoptosis Machinery

Curcumin-1,2,3-Triazole Conjugation for Targeting the Cancer Apoptosis Machinery

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C₃₀H₂₅FN₁₀S⋅C₃H₇NO

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1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships

Cited by 379 publications

References 328 publications

Curcumin-1,2,3-Triazole Conjugation for Targeting the Cancer Apoptosis Machinery

Curcumin-1,2,3-Triazole Conjugation for Targeting the Cancer Apoptosis Machinery

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C30H25FN10S⋅C3H7NO

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The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C₃₀H₂₅FN₁₀S⋅C₃H₇NO