Synthesis and biological evaluation of novel triazole substituted pyrazolyl-methylenehydrazinyl-5-arylidene thiazolidinone derivatives as antibacterial and cytotoxic agents

Pogaku, Vinay; Eslavath, Ravi Kumar; Dayakar, G; Singh, Surya S.; Basavoju, Srinivas

doi:10.1007/s11164-017-2978-4

Cited by 11 publications

(3 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A library of triazole-substituted pyrazolyl-methylenehydrazinyl-5-arylidene thiazolidinone analogs 7 was synthesized by Pogaku et al and evaluated as antibacterial and cytotoxic candidates. [27] Compound 7 a containing para chloro group on the benzylidene ring exhibited the highest cytotoxic activity against the MCF-7 cell line with an IC 50 value of 5.40 μM in comparison to the standard drug Doxorubicin with an IC 50 value of 4.50 μM (Figure 8). The authors noted that substituting electron-donating groups or electron-withdrawing at the para position of the benzylidene ring is vital for cytotoxic activity.…”

Section: Thiazolidinone-triazole Hybridsmentioning

confidence: 99%

Thiazolidinone‐Heterocycle Frameworks: A Concise Review of Their Pharmacological Significance

2023

View full text Add to dashboard Cite

Molecular hybridization is deemed an optimistic approach in drug design and the discovery of novel biologically active molecules as it may advance their affinity and potency while concurrently decreasing associated resistance and side effects. Approximately 20 % of approved drugs were developed using this approach in the past few years. Thiazolidinone is one of the privileged pharmacophores in medicinal chemistry and is associated with various biological activities; it forms a functional unit in several FDA-approved drugs. Consequently, this pharmacophore has attracted the attention of many research groups to further explore its pharmacological relevance by coupling it with other pharmacophoric moieties. This review presents a concise account of scholarly research exploits directed at the biological activities of newly synthesized thiazolidinone-tagged molecular hybrids. Focused attention is given to the existing structural activity relationship in each compound library and the toxicity profile of potent compounds including in silico docking studies (where applicable). This work would provide a base on which new pharmaceuticals with improved potency can be modelled.

show abstract

Section: Thiazolidinone-triazole Hybridsmentioning

confidence: 99%

Thiazolidinone‐Heterocycle Frameworks: A Concise Review of Their Pharmacological Significance

2023

View full text Add to dashboard Cite

show abstract

“…Pyrazoles represent major class of five membered heterocyclic compounds displaying diverse biological activities such as anticancer, [1] antitubercular, [2,3] antibacterial, [4,5] antiobesity, [6] antihistaminic [7] etc. [8,9] As demonstrated by the examples shown in Figure 1, Fipronil is a broadly used insecticide that belongs to the phenylpyrazole chemical family.…”

Section: Introductionmentioning

confidence: 99%

Transition Metal‐ and Oxidant‐Free Regioselective Synthesis of 3,4,5‐Trisubstituted Pyrazoles by Means of [3+2] Cycloaddition Reactions

2022

Self Cite

View full text Add to dashboard Cite

A highly efficient regioselective synthesis of 3,4,5-trisubstituted pyrazoles via transition metal-and oxidant-free, three component [3 + 2] cycloaddition with thiazolidinedione chalcones, benzaldehydes and N-tosylhydrazine is described. The reaction proceeds through CÀ C and CÀ N bond formations under mild reaction conditions to produce structurally diverse polysubstituted pyrazoles in moderate to good yields.

show abstract

“…For instance, the recent succinate dehydrogenase inhibitor (SDHI) fungicides pydiflumetofen, isoflucypram, and pyrapropoyne have pyrazole amide groups. Numerous biological activities can be performed by modifying the pyrazole scaffold, such as nematocidal [8][9][10], herbicidal [11,12], antimicrobial [13], antioxidant [14], fungicidal [15][16][17], anticancer [18], and insecticidal activities [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoromethylpyrazoyl moiety

et al. 2022

View full text Add to dashboard Cite

In order to find new lead compounds with high pesticidal activity, a series of 1,3,4-oxadiazole thioether compounds ( 5 series) were designed by using penthiopyrad as a synthon. They were synthesized easily via five steps by using ethyl 4,4,4-trifluoro-3-oxobutanoate and triethyl orthoformate as starting materials. The synthesized compounds were characterized by 1 H NMR, 13 C NMR and HRMS. The compound 2-(benzylthio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole ( 5a ) was further determined by X-ray single-crystal diffraction. It crystallized in the monoclinic system, space group P2 1 /c , Z = 4. All the 1,3,4-oxadiazole thioether derivatives were screened for fungicidal activity against ten fungi and herbicidal activity against two weeds. The bioassay results indicated that some of the synthesized 1,3,4-oxadiazole compounds exhibited good fungicidal activity (> 50% inhibition) against the plant pathogens Sclerotinia sclerotiorum and Rhizoctonia solani at 50 μg/mL. Some of them exhibited certain herbicidal activity, and compounds 2-((3-chlorobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole ( 5e) and 2-((4-bromobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole (5 g) had bleach effect. Molecular docking is to find the best fit orientation of the 2-((4-bromobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole (5 g) molecule with the SDH protein (PDB: 2FBW). The docking results indicate that the compound 5 g and the lead compound penthiopyrad have similar binding interactions with SDH and carbonyl is a key group for these compounds. Supplementary Information The online version contains supplementary material available at 10.1007/s11164-022-04839-x.

show abstract

Synthesis and biological evaluation of novel triazole substituted pyrazolyl-methylenehydrazinyl-5-arylidene thiazolidinone derivatives as antibacterial and cytotoxic agents

Cited by 11 publications

References 58 publications

Thiazolidinone‐Heterocycle Frameworks: A Concise Review of Their Pharmacological Significance

Thiazolidinone‐Heterocycle Frameworks: A Concise Review of Their Pharmacological Significance

Transition Metal‐ and Oxidant‐Free Regioselective Synthesis of 3,4,5‐Trisubstituted Pyrazoles by Means of [3+2] Cycloaddition Reactions

Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoromethylpyrazoyl moiety

Contact Info

Product

Resources

About