Synthesis, characterization and biological evaluation of some novel 2,4-thiazolidinediones as potential cytotoxic, antimicrobial and antihyperglycemic agents

Avupati, Vasudeva Rao; Yejella, Rajendra Prasad; Akula, Annapurna; Guntuku, Girija Sankar; Doddi, Bhagya Raju; Vutla, Venkata Rao; Anagani, Suvarna Ratna; Adimulam, Lakshmana Santhi; Vyricharla, Aruna Kumar

doi:10.1016/j.bmcl.2012.08.052

Cited by 43 publications

(25 citation statements)

References 61 publications

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“…It is notable that moderate activity was observed when the nitro groups are introduced on the phenyl ring at position 2 of the 1,5-benzothiazepineringas displayed in the case of compounds 4k and 4j with ED50 values 38.64±0.24 and 51.82±0.37 μg/mL. The compound 4s (ED50: 28.61±0.61 μg/mL) having phenylethylidene substitution position 2 of the 1,5-benzothiazepinering is also relevant for enhancing the cytotoxicity [22].…”

Section: Cytotoxicitymentioning

confidence: 94%

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

et al. 2014

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Section: Cytotoxicitymentioning

confidence: 94%

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

et al. 2014

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“…Molecular docking was performed with GTP using Molegro Virtual Docker 2010.4.0 (MDV2010.4.0). Molegro Virtual Docker software is best suited for all aspects of the docking process including preparation of the molecules to determination of the potential binding sites of the target protein, and prediction of the binding modes of the ligands [28]. This software is based on a new heuristic search algorithm that combines differential evolution with cavity prediction algorithm [29].…”

Section: Active Site Prediction and Molecular Dockingmentioning

confidence: 99%

Homology Modeling and characterization of Phosphoenolpyruvate Carboxykinase (PEPCK) from Schistosoma japonicum

Verma¹

2013

IOSR-JPBS

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Phosphoenolpyruvate carboxykinase (PEPCK), a carboxylase enzyme is present in all living organisms. It catalyzes metal-nucleotide coupled reversible decarboxylation and phosphorylation between phosphoenolpyruvate (PEP) and oxaloacetate (OAA) depending on the system and the availability of the intermediates. In fungi, plants and in most bacteria, production of PEP from OAA by PEPCK is the key step during gluconeogenesis. In healthy human cytosolic PEPCK enzyme is present only during glucose starvation; cytosolic PEPCK rapidly disappears on the replenishment of glucose due to hormonal control of the transcription of the cytosolic PEPCK-gene. In some parasitic helminthes like Ascaris suum, nematodes such as Haemonchus contortus, PEPCK carry out the reverse reaction to produce OAA from PEP. In Trypanosoma cruzi and all species of the genus Leishmania, this enzyme is very active even in the presence of high level of carbohydrate. There is a significant functional difference between parasitic PEPCK and mammalian host PEPCK. These differences between the mammalian host and the parasite enzyme strongly support the belief that PEPCK should be further investigated as a possible target for selective chemotherapeutic agents. The experimental 3D structure of PEPCK of Schistosoma japonicum is not available in protein data bank. Therefore, based on the knowledge of the best template (3DT7), model of 3D structure of Schistosoma japonicum PEPCK was prepared using Modeller v9.10 software and processed in to energy minimization, Ramachandran plot analysis, quality assessment and characterization.

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“…2,4‐Thiazolidinediones (TZDs) are an important class of compounds that enhance insulin action (insulin sensitizers) and promote glucose utilization in peripheral tissue . The chemistry of TZDs has attracted attention as they have been found to reveal several biological activities , such as antihyperglycemic , anti‐inflammatory , antimalarial , antioxidant , antitumor , cytotoxic , antimicrobial , and antiproliferative . Unlike sulfonylurea and biguanides which lead to severe hypoglycemia, TZDs are not associated with such hypoglycemic incidents.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Thiazolidine‐2,4‐dione Conjugates as PPAR‐γ Agonists

Nazreen

Alam

Hamid

et al. 2015

Archiv der Pharmazie

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A library of synthesized conjugates of phenoxy acetic acid and thiazolidinedione 5a-m showed potent peroxisome proliferator activated receptor-γ (PPAR-γ) transactivation as well as significant blood glucose lowering effect comparable to the standard drugs pioglitazone and rosiglitazone. Most of the compounds showed higher docking scores than the standard drug rosiglitazone in the molecular docking study. Compounds 5l and 5m exhibited PPAR-γ transactivation of 54.21 and 55.41%, respectively, in comparison to the standard drugs pioglitazone and rosiglitazone, which showed 65.94 and 82.21% activation, respectively. Compounds 5l and 5m significantly lowered the blood glucose level of STZ-induced diabetic rats. Compounds 5l and 5m lowered the AST, ALT, and ALP levels more than the standard drug pioglitazone. PPAR-γ gene expression was significantly increased by compound 5m (2.00-fold) in comparison to the standard drugs pioglitazone (1.5-fold) and rosiglitazone (1.0-fold). Compounds 5l and 5m did not cause any damage to the liver and could be considered as promising candidates for the development of new antidiabetic agents.

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Synthesis, characterization and biological evaluation of some novel 2,4-thiazolidinediones as potential cytotoxic, antimicrobial and antihyperglycemic agents

Cited by 43 publications

References 61 publications

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

Homology Modeling and characterization of Phosphoenolpyruvate Carboxykinase (PEPCK) from Schistosoma japonicum

Design, Synthesis, and Biological Evaluation of Thiazolidine‐2,4‐dione Conjugates as PPAR‐γ Agonists

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