Synthesis and biological activity of some new flavonyl-2,4-thiazolidinediones

Bozdağ‐Dündar, Oya; Verspohl, Eugen J.; Daş-Evcimen, Net; Kaup, Rebecca M.; Bauer, Katrin; Sarıkaya, Mutlu; Evranos, Begüm; Ertan, Rahmiye

doi:10.1016/j.bmc.2008.05.059

Cited by 47 publications

(23 citation statements)

References 28 publications

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“…Heterocyclic compounds, such as thiazoles, pyrrolidines and quinoxalines are important in many pharmaceutical applications (Bozdag -Dü ndar et al, 2008;Swarnkar et al, 2007;Verma & Saraf, 2008;He et al, 2003;Campeau et al, 2008;Muralikrishnan et al, 2013). The addition of bromine to these classes of compounds can offer valuable synthetic intermediates and provide additional medicinal benefits.…”

Section: Structure Descriptionmentioning

confidence: 99%

6′-(3-Bromophenyl)-7′-nitro-1′,6′,7′,7a'-tetrahydro-3′H-spiro[indeno[1,2-b]quinoxaline-11,5′-pyrrolo[1,2-c]thiazole]

Muthuselvi¹,

Muthu

Athimoolam

et al. 2018

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The title compound, C26H19BrN4O2S, crystallizes in a monoclinicC-centred lattice with eight molecules in the unit cell. The five-membered thiazole and pyrrolidine rings adopt envelope conformations and the bromophenyl and indenoquinoxaline planes are oriented at a dihedral angle of 61.6 (1)° to each other. The molecular structure features an intramolecular C—H...N interaction leading to anS(6) ring motif.C(9) andC(10) chains along thec- andb-axis directions form through C—H...Br and C—H...S contacts, respectively. In addition, C—H...O and C—H...N hydrogen bonds form inversion dimers withR22(10) andR22(14) motifs, respectively. One O atom is disordered over two positions (occupancy ratio 0.63:0.37).

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Section: Structure Descriptionmentioning

confidence: 99%

6′-(3-Bromophenyl)-7′-nitro-1′,6′,7′,7a'-tetrahydro-3′H-spiro[indeno[1,2-b]quinoxaline-11,5′-pyrrolo[1,2-c]thiazole]

Muthuselvi¹,

Muthu

Athimoolam

et al. 2018

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“…This is followed by the synthesis of number of amino acid derivatives such as N-[4-(benzoylamino)phenylsulfonyl]glycine (BAPSG) (Sunkara et al, 2000), N-benzoyl amino acids (Benvenuti et al, 1998), N-(benzyloxy) glycine derivatives (Macchia et al, 1998) as an effective ARIs. We also studied the AR inhibitory activities of benzodiazepine derivatives, 5-(3 0 -indolyl)-2-thiohydantoin derivatives, some pyridazine derivatives, 2-phenylindole derivatives, substituted-thiazolyl-thiazolidinedione derivatives (Buyukbingol et al, 1994;Daş-Evcimen et al, 1998;Ş üküroglu et al, 2007;Süzen et al, 2007;Bozdag-Dündar et al, 2007;Daş-Evcimen et al, 2008;Bozdag-Dündar et al, 2008a, b).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of rat kidney aldose reductase inhibitory activity of some N-acetyl dehydroalanine derivatives

et al. 2010

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Aldose reductase (AR) is an enzyme that catalyzes the conversion of glucose to sorbitol, which is in turn converted to fructose by sorbitol dehydrogenase. Increased AR activity has been implicated in the pathogenesis of diabetic complications such as neuropathy, nephropathy, retinopathy, and cataract. Inhibitors of AR thus seem to have the potential to prevent or treat diabetic complications. At present, however, side effects and/or insufficient pharmacokinetic profiles have made most of the drug candidates undesirable. In this study, the synthesis (l-o) and ARI activity of 15 N-acetyl dehydroalanine derivatives (a-o) are described. The synthesized compounds mainly contained aliphatic and aromatic side chains. The insertion of ethyl and chloro propyl side chains were shown to be more effective than the rest of the compounds. Between the synthesized compounds N-ethyl (b) and N-propylchloride (h) derivatives showed the best ARI activities.

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“…Previously, we reported the synthesis and insulin releasing activity of flavonyl-TZDs [8][9][10][11][12] , chromonyl-TZDs [13][14][15] and thiazolyl-TZDs [16][17][18] . A significant insulinotropic effect was seen with several of these TZD compounds.…”

Section: Research Articlementioning

confidence: 99%

Synthesis and antidiabetic activity of 2,4-thiazolidindione, imidazolidinedione and 2-thioxo-imidazolidine-4-one derivatives bearing 6-methyl chromonyl pharmacophore

Ceylan–Ünlüsoy

Kazak

Bayro

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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Synthesis and biological activity of some new flavonyl-2,4-thiazolidinediones

Cited by 47 publications

References 28 publications

6′-(3-Bromophenyl)-7′-nitro-1′,6′,7′,7a'-tetrahydro-3′H-spiro[indeno[1,2-b]quinoxaline-11,5′-pyrrolo[1,2-c]thiazole]

6′-(3-Bromophenyl)-7′-nitro-1′,6′,7′,7a'-tetrahydro-3′H-spiro[indeno[1,2-b]quinoxaline-11,5′-pyrrolo[1,2-c]thiazole]

Evaluation of rat kidney aldose reductase inhibitory activity of some N-acetyl dehydroalanine derivatives

Synthesis and antidiabetic activity of 2,4-thiazolidindione, imidazolidinedione and 2-thioxo-imidazolidine-4-one derivatives bearing 6-methyl chromonyl pharmacophore

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