Synthesis, Activity, and Molecular Modeling of New 2,4-Dioxo-5-(naphthylmethylene)-3-thiazolidineacetic Acids and 2-Thioxo Analogues as Potent Aldose Reductase Inhibitors

Fresneau, Patrick; Cussac, M.; Morand, Jean-Marc; Szymonski, B.; Tranqui, D.; Leclerc, G.

doi:10.1021/jm9801399

Cited by 51 publications

(27 citation statements)

References 50 publications

(108 reference statements)

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“…It was reported that NZ-314 (12) increased the motor nerve conduction velocity and the sciatic nerve blood flow compared to diabetic controls in STZ-induced rats. A 3-thiazolidineacetic acid derivative (13), which can be regarded as a cyclic derivative of 4, has been reported to be a potent ARI [26]. Recently, an indole derivative (14) with a benzothiazole moiety and its related compounds were patented as ARIs, showing excellent selectivity for AR over aldehyde reductase.…”

Section: Carboxylic Acidsmentioning

confidence: 99%

Molecular Modeling and Structure-based Drug Discovery Studies of Aldose Reductase Inhibitors

Miyamoto

2002

CBIJ

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Aldose reductase has been implicated in the etiology of diabetic complications. A variety of compounds have been observed to inhibit aldose reductase and effective, orally active inhibitors of the enzyme have been investigated for many years. Although several of these compounds have progressed to the clinical level, only one such drug is currently on the market. Due to the limited number of available drugs for the treatment of diabetic complications, a number of rational approaches for the discovery of aldose reductase inhibitors have been taken since the determination of the 3-dimensional structure of the enzyme. In this review, rational approaches such as the molecular modeling of aldose reductase and its complex structure and structure-based drug discovery are presented, following a short summary of known inhibitors.

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Section: Carboxylic Acidsmentioning

confidence: 99%

Molecular Modeling and Structure-based Drug Discovery Studies of Aldose Reductase Inhibitors

Miyamoto

2002

CBIJ

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“…Other long term side effects linked to diabetes as a result of excess free glucose in tissues include cataractogenesis and microangiopathy [4]. Aldose reductase complications have been widely researched [5,6] and there are concerted efforts by scientists to continuously searching for inhibitors by investigating different medicinal plants that may have therapeutic activities.…”

Section: Introductionmentioning

confidence: 99%

Characterization and Aldose Reductase Inhibitory Effect of Carica papaya Extract

E¹

2017

Pharm Anal Acta

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Objective and aim: the aim of the research work was to characterize the methanolic extract of C. papaya and then carried out the anti-diabetic inhibitory potential of the extract against Aldose Reductase enzymes. Materials and methodology:The C. papaya leaves were harvested fresh and air dried for five days at room temperature and blended into powdered form using electric blender. It was subsequently subjected to extraction using analytical grade of methanol solvent. Enzymatic reaction assays were performed using standard recommended protocol with slight modifications and the extract was characterized using Gc-Ms. Finally some of the identified compounds were screened for various degrees of drug characteristics using Online OSIRIS property explorer.Results: the IC50 value (1.22 ± 0.63 μg/mL) of ALR1 was better than the standard vaproic acid of IC50 (57.4 ± 10 μg/mL) and the IC50 (1.22+0.06 μg/mL) of ALR2 of the methanolic extract was better than the sorbinil standard IC50 (3.10 ± 0.20 μg/mL). The promising inhibitory aldose reductase may be due to the compounds present in the methanolic extract and these compounds include; phytol, Oxalic acid,6-ethyloct-3-yl isobutyl ester, 3,methyl-2-(2-oxopropyl)Furan, Carbonic acid, isobutyl undec-10-enyl ester, D-mannitol,1 decylsulfonyl and 1H-Imidazole,1(1-oxooctadecyl), these identified compounds possess different drug characteristics such as, solubility, mutagenic, irritability, H-bond acceptor and H-bond donor. Conclusion:The promising potent inhibitory activity of C. papaya showed that the plant leaves could be further researched into as alternative for resolving cataract eye problem associated with prolongs diabetes mellitus.

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“…[3][4][5] Besides, it was reported that some 2,4-TZDs have been used as antihyperglycemic 6 and aldose reductase (AR) inhibitory agents with dual activity. 7 There is a great interest in 2,4-TZD derivatives as aldose reductase inhibitors (ARIs), 7,8 since they can be viewed as hydantoin bioisosters potentially free of the hypersensitivity reactions which are linked to the presence of the hydantoin system.…”

Section: Introductionmentioning

confidence: 99%

A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones

Ibrahim¹,

Abdel-Hamed²,

El-Gohary³

2011

J. Braz. Chem. Soc.

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A condensação do 3-formilcromano (1) com tiazolidina-2,4-diona (2) produziu 5-[4-oxo-4H-croman-3-ila)metileno]-1,3-tiazolidina-2,4-diona (3). A reação de 3 com hidrato de hidrazina, fenil hidrazina e hidrocloreto de hidroxilamina produziu os derivados correspondentes pirazol e isoxazol 4-7. O composto 3 reagiu com tiouréia, guanidina e cianoguanidina para produzir os derivados correspondentes de pirimidina 8-10. Pirimido

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Synthesis, Activity, and Molecular Modeling of New 2,4-Dioxo-5-(naphthylmethylene)-3-thiazolidineacetic Acids and 2-Thioxo Analogues as Potent Aldose Reductase Inhibitors

Cited by 51 publications

References 50 publications

Molecular Modeling and Structure-based Drug Discovery Studies of Aldose Reductase Inhibitors

Molecular Modeling and Structure-based Drug Discovery Studies of Aldose Reductase Inhibitors

Characterization and Aldose Reductase Inhibitory Effect of Carica papaya Extract

A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones

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