Synthesis, characterization and cytotoxic activity evaluation of 4-(1,2,3-triazol-1-yl) salicylic acid derivatives

Ríos-Malváez, Zita G.; Cano‐Herrera, Ma.‐Angeles; Dávila-Becerril, Juan Carlos; Mondragón-Solórzano, Gustavo; Ramírez‐Apán, María Teresa; Morales‐Morales, David; Barroso-Flores, Joaquı́n; Benítez, Jonnathan Guadalupe Santillán; Unnamatla, M. V. Basavanag; García‐Eleno, Marco A.; González‐Rivas, Nelly; Cuevas-Yáñez, Erick

doi:10.1016/j.molstruc.2020.129149

Cited by 18 publications

(9 citation statements)

References 46 publications

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“…[ 28 ] Antiproliferative agents based on the triazole fused 2‐mercaptobenzimidazole scaffold ( VI ) were reported by Andrade et al [ 15 ] that showed significant apoptosis induction potential against the glioblastoma cell line (GBM). [ 15 ] In a similar finding, STAT3 inhibitors reported by Ríos‐Malváez et al [ 29 ] based on the salicylic acid tethered triazoles ( VII ) showed potent antiproliferative activity. Importantly, it is conceivable that the combination of the triazole scaffold with well‐established pharmacophores may lead to more potent therapeutic agents.…”

Section: Introductionsupporting

confidence: 58%

New 3‐(1H‐benzo[d]imidazol‐2‐yl)quinolin‐2(1H)‐one‐based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis‐inducing agents

Gaikwad

Bansod

Biradar

et al. 2021

Archiv der Pharmazie

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A series of 1,2,3‐triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI‐60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT‐474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT‐474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6‐diamidino‐2‐phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC‐1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

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Section: Introductionsupporting

confidence: 58%

New 3‐(1H‐benzo[d]imidazol‐2‐yl)quinolin‐2(1H)‐one‐based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis‐inducing agents

Gaikwad

Bansod

Biradar

et al. 2021

Archiv der Pharmazie

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“…13 C NMR spectrum showed three characteristic signals at δ 49.58, 62.61, and 67.65 ppm due to the ethyl linker chain having two aliphatic C-atoms and one carbon of the −OCH 2 group from the propargyl unit. The infrared spectrum showed characteristic absorption peaks at 1448, 1240, and 3142 cm –1 corresponding to NN aromatic, cyclic N–NN, and C–H proton, indicating formation of the 1,2,3-triazole ring. , In the UV–vis spectrum, compound 6a showed a characteristic broad spectrum with maxima at around 330 nm, which could be attributed to the π–π* transitions of the 2-HBT skeleton. Finally, the structure of 6a was supported and assigned at m / z 480.14 (molecular ion) peak for C 27 H 21 N 5 O 2 S in electrospray ionization mass spectrometry (ESI-MS).…”

Section: Resultsmentioning

confidence: 99%

1,2,3-Triazoles of 8-Hydroxyquinoline and HBT: Synthesis and Studies (DNA Binding, Antimicrobial, Molecular Docking, ADME, and DFT)

2021

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A new series of 1,2,3-triazole hybrids containing either 2- or 4-hydroxyphenyl benzothiazole (2- or 4-HBT) and naphthalen-1-ol or 8-hydroxyquinoline (8-HQ) was synthesized in high yields and fully characterized. In vitro DNA binding studies with herring fish sperm DNA (hs-DNA) showed that quinoline- and 2-HBT-linked 1,2,3-triazoles of shorter alkyl linkers such as 6a are better with a high binding affinity (3.90 × 105 L mol–1) with hs-DNA as compared to naphthol- and 4-HBT-linked 1,2,3-triazoles bound to longer alkyl linkers. Molecular docking of most active 1,2,3-triazoles 6a–f showed high binding energy of 6a (−8.7 kcal mol–1). Also, compound 6a displayed considerable antibacterial activity and superior antifungal activity with reference to ciprofloxacin and fluconazole, respectively. The docking results of the fungal enzyme lanosterol 14-α-demethylase showed high binding energy for 6a (−9.7 kcal mol–1) involving dominating H-bonds, electrostatic interaction, and hydrophobic interaction. The absorption, distribution, metabolism, and excretion (ADME) parameter, Molinspiration bioactivity score, and the PreADMET properties revealed that most of the synthesized 1,2,3-triazole molecules possess desirable physicochemical properties for drug-likeness and may be considered as orally active potential drugs. The electrophilicity index and chemical hardness properties were also studied by density functional theory (DFT) using the B3LYP/6-311G(d,p) level/basis set.

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“…For the synthesis of triazole, many scholars have tried various synthetic methods and obtained different experimental yields. At present, the main synthesis methods of triazole are as follows: one is the substrate alkynylated firstly and then reacted with the azide compounds, [23–25] the other is the substrate azided firstly and then reacted with the alkynyl group [26–33] . Besides, when Marepu et al [34] .…”

Section: Resultsmentioning

confidence: 99%

“…At present, the main synthesis methods of triazole are as follows: one is the substrate alkynylated firstly and then reacted with the azide compounds, [23][24][25] the other is the substrate azided firstly and then reacted with the alkynyl group. [26][27][28][29][30][31][32][33] Besides, when Marepu et al [34] studied the anti-bacterial activity…”

Section: Synthetic Chemistrymentioning

confidence: 99%

Synthesis and Primary Biological Evaluation of Triazole‐Modified Picroside II Compounds

Yang

Kong

et al. 2021

ChemistrySelect

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Picroside II, an iridoid glycoside, has anti‐cancer, anti‐virus, anti‐apoptotic, nervous and myocardial protection effects and so on. However, the oral bioavailability of Picroside II is low, and the half‐life in vivo is short, so it is limited to use in clinic. Triazole is a highly stable heterocyclic ring, which can be interacted with various enzymes or receptors in the organism through non‐covalent interactions, and many of its good pharmacological activities in vitro and in vivo have been reported. Based on the advantages of triazole and Picroside II, a series of triazole‐modified Picroside II derivatives (5 a–5 i) were synthesized by using drug combination principles for the first time. The structures were confirmed by different spectroscopic techniques including 1H NMR, 13C NMR and HRMS, and the primary biological evaluation of anti‐breast cancer, anti‐colorectal cancer, the effect on SARS‐CoV‐2 3CLpro inhibitor, and CD47‐SIRPα protein were screened as well. Compound 5 e has anti‐breast cancer activity, and compounds 3 and 5 i have anti‐colorectal cancer activity.

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Synthesis, characterization and cytotoxic activity evaluation of 4-(1,2,3-triazol-1-yl) salicylic acid derivatives

Cited by 18 publications

References 46 publications

New 3‐(1H‐benzo[d]imidazol‐2‐yl)quinolin‐2(1H)‐one‐based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis‐inducing agents

New 3‐(1H‐benzo[d]imidazol‐2‐yl)quinolin‐2(1H)‐one‐based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis‐inducing agents

1,2,3-Triazoles of 8-Hydroxyquinoline and HBT: Synthesis and Studies (DNA Binding, Antimicrobial, Molecular Docking, ADME, and DFT)

Synthesis and Primary Biological Evaluation of Triazole‐Modified Picroside II Compounds

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