Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

Chaturvedi, Radha Nandan; Pendem, Krishnaiah; Patel, Vipul P.; Sharma, Manu; Malhotra, Sunita

doi:10.1007/s00706-018-2207-x

Cited by 12 publications

(8 citation statements)

References 39 publications

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“…While thiazolidinedione derivatives were previously developed, a series of analogous indanones provided valuable results, especially compound 123 which revealed a very good affinity for PPARγ (IC 50 = 0.62 μM). 184 Recently, the protein mitoNEET, a mitochondrial 2Fe-2S iron−sulfur cluster, was discovered along with its important role in both diabetes and obesity processes. Through a screening of mitoNEET potential ligands, three aurones were identified.…”

Section: Neurochemical Activities Inhibition Of Monoamine Oxidases (M...mentioning

confidence: 99%

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

et al. 2022

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Hemiindigoids comprise a range of natural and synthetic scaffolds that share the same aromatic hydrocarbon backbone as well as promising biological and optical properties. The encouraging therapeutic potential of these scaffolds has been unraveled by many studies over the past years and uncovered representants with inspiring pharmacophoric features such as the acetylcholinesterase inhibitor donezepil and the tubulin polymerization inhibitor indanocine. In this review, we summarize the last advances in the medicinal potential of hemiindigoids, with a special attention to molecular design, structure–activity relationship, ligand-target interactions, and mechanistic explanations covering their effects. As their strong fluorogenic potential and photoswitch behavior recently started to be highlighted and explored in biology, giving rise to the development of novel fluorescent probes and photopharmacological agents, we also discuss these properties in a medicinal chemistry perspective.

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Section: Neurochemical Activities Inhibition Of Monoamine Oxidases (M...mentioning

confidence: 99%

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

et al. 2022

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“…Interesting to note, that in this work electron withdrawing groups on a iodoaryl moiety were essential for cyclization to appear alongside the coupling reaction. In order to avoid cyclization of our products, the synthesis of desired compounds 1d,e was performed without the base and after work-up procedure, the obtained materials were isolated in good yields (Table 1, entries 4,5). Reaction between 2-mercaptomethylbenzimidazole and 1-(3-bromo-prop-1-yn-1-yl)-4-nitrobenzene was ambiguous and no product was isolated.…”

Section: Resultsmentioning

confidence: 99%

“…Due to the cyclization of formed products 1d-e to the 3-(4-substituted benzyl)benzo [4,5]imidazo[2,1-b]thiazoles C1-2 in basic reaction media, synthesis of compounds 1d-e was performed in same conditions without NaOH. After reaction completion EtOH was evaporated, residue was dissolved in ethyl acetate and washed with saturated NaHCO 3 aqueous solution.…”

Section: Discussionmentioning

confidence: 99%

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Study on halogen promoted cyclization of 2‐alkynylthiobenzimidazoles

Misiūnaitė

Bukšnaitienė

Pošiūnas

et al. 2022

Journal of Heterocyclic Chem

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Electrophile promoted nucleophilic cyclization of 2-alkynylthiobenzimidazoles was investigated. N-halosuccinimides were chosen as electrophile source in formation of substituted benzimidazo[2,1-b]thiazoles and benzimidazo[2,1-b] [1,3]thiazines. Reaction pathway via 6-endo-dig or 5-exo-dig cyclization of substrates depended on substituents to the alkyne moiety, though with bromine electrophile in some cases benzimidazole moiety predominated alkyne and aromatic substitution reaction was observed. Compounds with prolonged linkage in 2-(propynylthio)methylbenzimidazoles formed only 7-endo-dig products.

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“…For example, it is claimed that some 2-substituted thiazolo[3,2- a ]benzimidazol-3-ones (Figure A) have antitrichinellosis activity . Certain benzylidene benzimidazo[2,1- b ]thiazolinones (Figure B) were studied as antifungal agents, several thiazolobenzimidazole derivatives (Figure C) exhibit lipid peroxidation inhibition effects, and some substituted benzimidazo[2,1- b ]thiazolinones (Figure D) might have antidiabetic activity …”

mentioning

confidence: 99%

One-Pot Synthesis of Benzimidazo[2,1-b]thiazoline Derivatives through an Addition/Cyclization/Oxidative Coupling Reaction

Wang

et al. 2020

J. Org. Chem.

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A novel and efficient approach to the synthesis of benzimidazo[2,1-b]thiazoline derivatives has been developed through an addition/cyclization/intramolecular oxidative C−H functionalization process. A variety of alkylene benzimidazo[2,1-b] thiazolines were conveniently assembled from the reaction of aryl isothiocyanate and propargylic amine in the presence of Cu(OAc) 2 and PIFA at room temperature. The product could be further converted to substituted benzimidazo[2,1-b]thiazole derivatives.

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Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

Cited by 12 publications

References 39 publications

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

Study on halogen promoted cyclization of 2‐alkynylthiobenzimidazoles

One-Pot Synthesis of Benzimidazo[2,1-b]thiazoline Derivatives through an Addition/Cyclization/Oxidative Coupling Reaction

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