Design, synthesis of novel (Z)-2-(3-(4-((3-benzyl-2,4-dioxothiazolidin-5-ylidene)methyl)-1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide derivatives: Evaluation of cytotoxic activity and molecular docking studies

Kolluri, Prashanth Kumar; Gurrapu, Nirmala; Subhashini, N; Putta, Shravani; Singh, Surya S.; Vani, Tamalapakula; Manga, Vijjulatha

doi:10.1016/j.molstruc.2019.127300

Cited by 6 publications

(3 citation statements)

References 42 publications

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“…Moreover, The ADME calculation results revealed that all the synthesized derivatives possess drug-likeness properties. [113] Based on the combination principles, Qui et al reported the design and synthesis of novel TZD and parthenolide hybrids (61, Figure 33) via click chemistry. The synthesized compounds were further evaluated for cytotoxic activity on human cancer cell lines, including human erythroleukemia cell line (HEL), prostate (PC3), and breast (MDA-MB-231) by using MTT assay.…”

Section: N-3 and C-5 Disubstituted Tzdsmentioning

confidence: 99%

The medicinal perspective of 2,4‐thiazolidinediones based ligands as antimicrobial, antitumor and antidiabetic agents: A review

Singh

Kajal

Pradhan

et al. 2022

Archiv der Pharmazie

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2,4-Thiazolidinedione (2,4-TZD), commonly known as glitazone, is a ubiquitous heterocyclic pharmacophore possessing a plethora of pharmacological activities and offering a vast opportunity for structural modification. The diverse range of biological activities endowed with a novel mode of action, low cost, and easy synthesis has attracted the attention of medicinal chemists. Several researchers have integrated the TZD core with different structural fragments to develop a wide range of lead molecules against various clinical disorders. The most common sites for structural modifications at the 2,4-TZD nucleus are the N-3 and the active methylene at C-5. The review covers the recent development of TZD derivatives such as antimicrobial, anticancer, and antidiabetic agents. Various 2,4-TZD based agents or drugs, which are either under clinical development or in the market, are discussed in the study. Different synthetic methodologies for synthesizing the 2,4-TZD core are also included in the manuscript.The importance of various substitutions at N-3 and C-5 and the mechanisms of action and structure-activity relationships are also discussed. We hope this study will serve as a valuable tool for the scientific community engaged in the structural exploitation of the 2,4-TZD core for developing novel drug m\olecules for life-threatening ailments.

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Section: N-3 and C-5 Disubstituted Tzdsmentioning

confidence: 99%

The medicinal perspective of 2,4‐thiazolidinediones based ligands as antimicrobial, antitumor and antidiabetic agents: A review

Singh

Kajal

Pradhan

et al. 2022

Archiv der Pharmazie

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“…The reported compound benzyl‐1 H ‐indole‐3‐carbaldehyde( 3 ) was prepared by N ‐benzylation of indole‐3‐carboxaldehyde ( 1 ) with benzyl bromide ( 2 ) in the presence of anhydrous K 2 CO 3, stirred at room temperature for 3 hrs [32] . Compound 3 was subjected to Knoevenagel condensation with thiazolidine‐2,4‐dione ( 4 ) in the presence of catalytic amount of piperidine, a few drops of glacial acetic acid and refluxed in toluene for 8 h to afford the (Z)‐5‐((1‐benzyl‐1 H ‐indol‐3‐yl)methylene)thiazolidine‐2,4‐dione ( 5 ) [33] . Which on N ‐alkylation with propargyl bromide ( 6 ) yielded (Z)‐5‐((1‐benzyl‐1 H ‐indol‐3‐yl)methylene)‐3‐(prop‐2‐yn‐1‐yl)thiazolidine‐2,4‐dione ( 7 ) at room temperature in presence of dry potassium carbonate in DMF.…”

Section: Resultsmentioning

confidence: 99%

“…[32] Compound 3 was subjected to Knoevenagel condensation with thiazolidine-2,4-dione (4) in the presence of catalytic amount of piperidine, a few drops of glacial acetic acid and refluxed in toluene for 8 h to afford the (Z)-5-((1-benzyl-1H-indol-3-yl)methylene)thiazolidine-2,4-dione (5). [33] Which on N-alkylation with propargyl bromide (6) yielded (Z)-5-((1-benzyl-1Hindol-3-yl)methylene)-3-(prop-2-yn-1-yl)thiazolidine-2,4-dione (7) at room temperature in presence of dry potassium carbonate in DMF. The intermediate (7) on further reaction with various substituted aryl azides (8 a-l) formed the corresponding triazoles, by click reaction conditions.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Anticancer Activity and Molecular Docking Studies of Hybrid Molecules Containing Indole‐Thiazolidinedione‐Triazole Moieties

et al. 2022

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A library of twelve hybrid molecules containing Indole-Thiazolidinedione-Triazole moieties were synthesized by following a series of N-benzylation, Knoevenagel condensation and click chemistry reactions. The structure of novel molecules confirmed by spectral analysis data of 1 H-NMR, 13 C-NMR and LC-MS. All the compounds screened for their anticancer activity against the human liver cancer HePG-2, human colorectal cancer HCT-116, human prostate cancer PC-3, and human breast cancer MCF7 cell lines. MTT assay protocol was em-ployed and calculated IC 50 value of all compounds. Doxorubicin was used as standard drug. m-acetylphenyl substituted compound 9 i specified outstanding activity against four cell lines compared to doxorubicin. The p-acetylphenyl and p-nitrophenyl substituted compounds showed moderate activity against the same. Molecular docking studies were performed on EGFR, CDK2 and sorcin using Autodock Vina of PyRx tool. The binding energies and interactions acquired from docking results of compounds supported the investigational data.

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Design and synthesis of novel (Z)-5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-3-((1-substituted phenyl-1H-1,2,3-triazol-4-yl)methyl)thiazolidine-2,4-diones: a potential cytotoxic scaffolds and their molecular modeling studies

Subhashini

Kumar

et al. 2020

Mol Divers

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Design, synthesis of novel (Z)-2-(3-(4-((3-benzyl-2,4-dioxothiazolidin-5-ylidene)methyl)-1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide derivatives: Evaluation of cytotoxic activity and molecular docking studies

Cited by 6 publications

References 42 publications

The medicinal perspective of 2,4‐thiazolidinediones based ligands as antimicrobial, antitumor and antidiabetic agents: A review

The medicinal perspective of 2,4‐thiazolidinediones based ligands as antimicrobial, antitumor and antidiabetic agents: A review

Synthesis, Anticancer Activity and Molecular Docking Studies of Hybrid Molecules Containing Indole‐Thiazolidinedione‐Triazole Moieties

Design and synthesis of novel (Z)-5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-3-((1-substituted phenyl-1H-1,2,3-triazol-4-yl)methyl)thiazolidine-2,4-diones: a potential cytotoxic scaffolds and their molecular modeling studies

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