Synthesis and antiproliferative activity of Daidzein bridged bis-[1,2,3]-triazole derivatives: Double click strategy

Yerrabelly, Jayaprakash Rao; Gogula, Thirupathi; Erukala, Yadaiah Goud; Hemasri, Y.; Gabriella, Srujana

doi:10.1016/j.cdc.2020.100523

Cited by 7 publications

(6 citation statements)

References 30 publications

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“…[29] The bis-[1,2,3]triazole-daidzein hybrids, compounds 4-6, showed significant activity, with a GI 50 value close to 0.14 μM against HeLa and MDA-MB-231 cell lines as compared to the standard drug, nocodazole (GI 50 < 0.01). [30] Novel 1,2,3-triazole-tethered cholesterol and ergosterol hybrids, [2,5-furandiylbis(methylene)]bis(cholest-5-en-3-yl-1H-1,2,3-triazole-4-pentanoate) (7) showed cytotoxicity with an IC 50 value of 205.06 μM against the MCF-7 cancer cell line and [2,5-furandiylbis (methylene)]bis(ergosta-5,7,22-trien-3-yl-1H-1,2,3-triazole-4-propanoate) (8) showed an IC 50 value of 59.5 μM toward the HT29 cancer cell line. [31] Novel 1,2,3-triazole hybrids of myrrhanone B, 9 and 10 among the tested compounds, were the most potent antiproliferative agents against the PC-3 cell line.…”

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confidence: 99%

“…[45] 1,2,3-Triazole containing coumarin ring 29 (IC 50 value of 2.97 μM) was found to be more potent than cisplatin (IC 50 value of 24.15 μM) and induced sub-G1 phase arrest, increased apoptosis, and promoted the production of reactive oxygen species (ROS). [46] Incorporation of isatin into the 1,2,3-triazole-tethered coumarin hybrid (30) showed cytotoxicity, with an IC 50 value of 18.67 μM against A549 cells. [47,48] 1,2,3-Triazole-incorporated asiatic acid derivative 31 was found to be active, with IC 50 values in the range 2.67-4.84 μM against the three tested lung cancer cells.…”

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1,2,3‐Triazole hybrids as anticancer agents: A review

Alam

2021

Archiv der Pharmazie

155

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Despite the advancements in the development of anticancer agents, more effective and safer anticancer drugs still need to be developed as the current agents cause unwanted side effects and many patients have become drug resistant. 1,2,3-Triazoles, due to their remarkable biological potential, have received considerable attention in drug discovery for the development of anticancer agents. The present review article presents an overview of the recent advances in 1,2,3-triazole hybrids with anticancer potential over the last 2 years, their chemical structures, structure-activity relationships, and mechanisms of action, as well as insights into the docking studies.

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confidence: 99%

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1,2,3‐Triazole hybrids as anticancer agents: A review

Alam

2021

Archiv der Pharmazie

155

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“…[91] Incorporation of the second 1,2,3-triazole moiety was also tolerated, and hybrid 66 (GI 50 : 1.97-3.28 µM, SRB assay) showed promising antiproliferative activity against HS 578 T, MDA-MB-231 and MDA-MB-468 breast cancer cell lines, [92] whereas hybrids 67 (IC 50 : 0.14-12.2 µM, MTT assay) possessed considerable antiproliferative activity against MDA-MB-231 breast cancer cells. [93] For hybrids 67, overcome multidrug-resistant cancers with BCRP overexpression. [94] In the mice model, Ac 15 (Az 8 ) 2 (45 mg/kg, intraperitoneal injection) significantly reversed BCRP-mediated topotecan resistance without serious body weight loss or death incidence.…”

Section: 23-triazole-azole Hybridsmentioning

confidence: 99%

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

Song,

Zhang,

Zhang

et al. 2023

Archiv der Pharmazie

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Breast cancer, as one of the most common invasive malignancies and the leading cause of cancer‐related deaths in women globally, poses a significant challenge in the world health system. Substantial advances in diagnosis and treatment have significantly improved the survival rate of breast cancer patients, but the number of incidences and deaths of breast cancer are projected to increase by 40% and 50%, respectively, by 2040. Chemotherapy is one of the principal treatments for breast cancer therapy, but multidrug resistance and severe side effects remain the major obstacles to the success of treatment. Hence, there is a vital need to develop novel chemotherapeutic agents to combat this deadly disease. 1,2,3‐Triazole, which can be effectively constructed by click chemistry, not only can serve as a linker to connect different anti‐breast cancer pharmacophores but also is a valuable pharmacophore with anti‐breast cancer potential and favorable properties such as hydrogen bonding, moderate dipole moment, and enhanced water solubility. Particularly, 1,2,3‐triazole‐containing hybrids have demonstrated promising in vitro and in vivo anti‐breast cancer potential against both drug‐sensitive and drug‐resistant forms and possessed excellent selectivity by targeting different biological pathways associated with breast cancer, representing privileged scaffolds for the discovery of novel anti‐breast cancer candidates. This review concentrates on the latest advancements of 1,2,3‐triazole‐containing hybrids with anti‐breast cancer potential, including work published between 2020 and the present. The structure–activity relationships (SARs) and mechanisms of action are also reviewed to shed light on the development of more effective and multitargeted candidates.

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“…Compound 2.195f was found to be a close competitor of the positive control against breast cancer cell line (MDA-MB-231) (Scheme 2.37). 54 A series of heteroditopic receptors were synthesized to study the cooperative recognition of halide anions via sodium cation-benzo-crown ether binding. For example, the synthesis of the iodo containing receptor 2.198 (Scheme 2.38), two equivalents of 4-azido-benzo-15-crown-5 2.197 and 3,5-diiodoethynylpyridine 2.196 were reacted under modified CuAAC conditions to get the desired compound in 84% yield after recrystallization.…”

Section: Scheme 235mentioning

confidence: 99%

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Pathak¹,

Pan²

2022

Arkivoc

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A typical 1,2,3-triazoles are important aromatic heterocyclic compounds with three adjacent nitrogen atoms. These "unnatural" heterocycles found applications in pharmaceutical science, material science and chemical biology. Oligo-1,2,3-triazole linked molecules showed interesting applications in the field of DNA binding, selfassembly, surface modification, supramolecular chemistry etc. In this article, oligo-1,2,3-triazoles are broadly classified into two categories: (i) 1,2,3-triazoles are connected through varieties of organic molecules and (ii) triazole units are connected with one another either by N-(CH)n-C linkages or by amide bonds generated from amino acids. Syntheses and properties of some of these oligomers are reviewed in this article.

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Synthesis and antiproliferative activity of Daidzein bridged bis-[1,2,3]-triazole derivatives: Double click strategy

Cited by 7 publications

References 30 publications

1,2,3‐Triazole hybrids as anticancer agents: A review

1,2,3‐Triazole hybrids as anticancer agents: A review

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

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