Design, synthesis and biological evaluation of novel pyridine-thiazolidinone derivatives as anticancer agents: Targeting human carbonic anhydrase IX

Ansari, Mohammad Fawad; Idrees, Danish; Hassan, Md. Imtaiyaz; Ahmad, Kamal; Avecilla, Fernando; Azam, Amir

doi:10.1016/j.ejmech.2017.12.049

Cited by 76 publications

(47 citation statements)

References 52 publications

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“…3). Atropoisomers by rotation around C(6)-C (7) and N(2)-C (14) bonds are present in the structure [18]. Figure 4 shows two enantiomers observed in the crystal structure.…”

Section: Resultsmentioning

confidence: 97%

“…As stated earlier, among a number of targets, 4‐thiazolidinones also have ability to inhibit the activity of CAIX . To check the affinity of developed compounds against this protein, we carried out docking studies against CAIX protein (PDB ID: 3IAI).…”

Section: Computational Studiesmentioning

confidence: 99%

“…Both organic and organometallic pharmacophores are being designed and studied using docking, simulation, and other programs to delineate the mechanism of action of new compounds [22][23][24]. As stated earlier, among a number of targets, 4thiazolidinones also have ability to inhibit the activity of CAIX [18]. To check the affinity of developed compounds against this protein, we carried out docking studies against CAIX protein (PDB ID: 3IAI).…”

Section: Computational Studiesmentioning

confidence: 99%

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Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Mushtaque¹,

Avecilla

Hafeez

et al. 2019

Journal of Heterocyclic Chem

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Scaffolds containing one or more heteroatoms are ubiquitous in nature and are responsible for almost every biological processes in flora and fauna. The fact that heterocyclic cores have high propensity for biological targets, several nitrogen, oxygen, and sulfur‐containing heterocyclic compounds have been reported in the last few decades. One such intriguing class is 4‐thiazolidinone that exhibit diverse range of pharmacological activities. In the present study, we report synthesis, characterization, molecular docking, and anticancer evaluation of 10 new 4‐thiazolidinone analogues (5–14). One of the compounds (11) was structurally characterized using single crystal X structure. Anticancer evaluation against hepatocellular carcinoma cell line (HepG2) revealed that compound (7) was the most potent (IC50 = 75 μM) while other showed moderate to low activity (85–530 μM). To underpin the druggability and possible modes of action, drug‐likeness was determined and docking studies were carried out against β‐carbonic anhydrase receptor (PDB ID: 3IA). Attempts have also been made to establish a structure–activity relationship of the reported compounds.

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“…3). Atropoisomers by rotation around C(6)-C (7) and N(2)-C (14) bonds are present in the structure [18]. Figure 4 shows two enantiomers observed in the crystal structure.…”

Section: Resultsmentioning

confidence: 97%

Section: Computational Studiesmentioning

confidence: 99%

Section: Computational Studiesmentioning

confidence: 99%

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Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Mushtaque¹,

Avecilla

Hafeez

et al. 2019

Journal of Heterocyclic Chem

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“…Synthesis, cytotoxicity and anticancer activity of pyridine-thiazolidinones were reported by Ansari et al [123]. To obtain unique human CAIX inhibitors, the synthesis was carried out with the mixture of 3-(furan-2-ylmethyl)-2-(phenylimino)-1,3-thiazolidin-4-one, aldehydes and hexahydropyridine using ethanol (Scheme 72).…”

Section: Scheme 70 Synthesis Of Pyrazolo-oxothiazolidine Derivatives mentioning

confidence: 99%

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

Top Curr Chem (Z)

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In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

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“…The absorbance was observed at 595 nm on an ELISA-reader, and the survival ratio of living cells to untreated cells was expressed as a percentage. Each experiment was performed at least three times [23]. The IC 50 value of the test compound was shown in Table 1.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

1-(4-Hexylbenzoyl)-3-methylthiourea

Ruswanto

Mardianingrum

Lestari

et al. 2018

Molbank

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The 1-(4-hexylbenzoyl)-3-methylthiourea compound has been successfully synthesized by reacting 4-hexylbenzoyl chloride and 1-methylthiourea via the reflux method using a triethylamine catalyst. The 1-(4-hexylbenzoyl)-3-methylthiourea compound was identified by UV-visible, FT-IR, 13 C/ 1 H-NMR and Mass spectrophotometry. From the activity test on four cancer cell lines (HeLa, T47D, WiDr and MCF7 cell), it could be seen that it had better activity on four cancer cells than the control, hydroxyurea.

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Design, synthesis and biological evaluation of novel pyridine-thiazolidinone derivatives as anticancer agents: Targeting human carbonic anhydrase IX

Cited by 76 publications

References 52 publications

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

1-(4-Hexylbenzoyl)-3-methylthiourea

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