Synthesis and antidiabetic activity of some new chromonyl-2,4-thiazolidinediones

Ceylan–Ünlüsoy, Meltem; Verspohl, Eugen J.; Ertan, Rahmiye

doi:10.3109/14756360903357544

Cited by 23 publications

(14 citation statements)

References 20 publications

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“…) were synthesized by Knoevenagel reaction of 2‐formyl chromone/3‐formyl chromone with thiazolidine‐2,4‐dione/imidazolidine‐2,4‐dione/2‐thioxoimidazolidine‐4‐one using acetic acid/sodium acetate mixture. Methyl and ethyl substituted compounds, CD2, CD3, CD5, CD6, CD8, CD9, CD11, CD12 and CD13 were obtained by reacting non‐substituted compounds with methyl iodine and ethyl iodide in dimethylformamide/anhydrous sodium carbonate mixture as described in a previous paper . ‐Hexaoxacyclooctadecane (18‐crown‐6), 4,5‐dihydroxy‐1,3‐benzene‐disulfonic acid (tiron), 5,5‐dimethyl‐1‐pyrroline‐1‐oxide (DMPO), NH 4 Fe ( SO 4 ) 2 ⋅ 12 H 2 O (MW = 482.2), FeCl 3 ⋅ 6 H 2 O , CH 3 COOH, CH 3 COONa were obtained from Merck (Darmstadt, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…These compounds play an important protective role and counteract the onset and progression of several diseases of the free radical etiology. Owing to the importance of the chromone‐based compounds, recently we synthesized a novel group of chromone derivatives (CDs; chromonyl‐2,4‐thiazolidinediones, chromonyl‐2,4‐imidazolidinediones, chromonyl‐2‐thioxoimidazolidine‐4‐ones) possessing antidiabetic activity and presented their synthesis . In this paper, we have attempted to explain the origin of antidiabetic properties by evaluating the antioxidant activity of these compounds using chemiluminescence (CL), electron spin resonance (ESR), spin trapping and total antioxidant activity test.…”

Section: Introductionmentioning

confidence: 99%

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Studies on the antioxidant activities of some new chromone compounds

et al. 2014

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Recent reviews evidence that the naturally occurring compounds containing the chromone skeleton exhibit antiradical activities, providing protection against oxidative stress. The antioxidant activities of 13 new synthesized chromonyl-2,4-thiazolidinediones, chromonyl-2,4-imidazolidinediones and chromonyl-2-thioxoimidzolidine-4-ones were evaluated using in vitro antioxidant assays, including superoxide anion radical (O2(-•)), hydroxyl radical (HO(•)), 2,2-diphenyl-1-picryl-hydrazyl free radical (DPPH(•)) scavenging capacity and total antioxidant capacity ferric ion reducing activity. Superoxide anion radical was produced using potassium superoxide/18-crown-6-ether dissolved in dimethylsulfoxide, and the Fenton-like reaction (Fe(II) + H2O2) was a generator of hydroxyl radicals. Chemiluminescence, spectrophotometry, electron paramagnetic resonance (EPR) and 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as the spin trap were the measurement techniques. The results showed that the majority of the chromone derivatives tested showed a strong scavenging effect towards free radicals, similar to the chemiluminescence reaction with superoxide anion radical with a high activity, inhibition of the DMPO-OOH radical EPR signal (24-58%), the DMPO-OH radical EPR signal (4-75%) and DPPH radical EPR signal (6-100%) at 1 mmol/L. Several of the examined compounds exhibited the high reduction potentials. The results obtained show that the new synthesized chromone derivatives may directly scavenger reactive oxygen species and thus may play a protective role against oxidative damage.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Studies on the antioxidant activities of some new chromone compounds

et al. 2014

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“…Compounds 4-7 and 11-17 were prepared by alkylation of compounds 1-3 and 8-10 with methyl / ethyl iodide in the presence of anhydrous sodium carbonate/ dimethyl formamide (DMF). The synthesis and antidiabetic activities of these compounds were reported in our previous paper (6,14). All other chemicals used were analytical grade.…”

Section: Methodsmentioning

confidence: 99%

“…Previously, we reported the synthesis and antidiabetic activity of some chromonyl-thiazolidinedione derivatives (6). Some of them have been shown to have good antidiabetic activities.…”

Section: Introductionmentioning

confidence: 99%

Alterations of aldose reductase and superoxide dismutase activities by some chromonyl-2, 4-thiazolidinedione derivatives

AMİRZADEH-KHİABANİ¹

2014

Ankara Üniversitesi Veteriner Fakültesi Dergisi

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Summary: Persistent hyperglycemia in diabetes mellitus (DM) leads to progression of secondary complications, such as neuropathy, nephropathy and retinopathy, which cause irreversible damage once initiated. During states of hyperglycemia, the polyol pathway has increased activity. As a result of the increased polyol pathway activity and the overutilization of NADPH by the enzyme aldose reductase (AR), a number of other homeostatic mechanisms are compromised. In view of the complex metabolic changes induced by hyperglycemia in which AR is critically involved and the prominent role performed by oxidative stress, derivatives endowed with dual activity as AR inhibitors (ARIs) and antioxidant agents could thus represent a promising way forward in the search for useful drugs to treat long-term complications associated with DM. However, many of the clinically tested aldose reductase inhibitors (ARIs) proved to be inadequate as drug candidates because of adverse pharmacokinetics, toxic side effects or low efficacy. For these reasons, nowadays the design of the ARIs which do not cause side effects is still carried on. In our study, AR enzyme was purified from bovine lens tissues. Then, the probable effects of 17 different chromonyl-2,4-thiazolidinedione derivatives on aldose reductase and superoxide dismutase (SOD) enzymes were investigated. Depending upon the results, compounds named 1 and 8 showed the best AR inhibitory activity at the ratio of 52.56% and 58.73 %, respectively. The most activator effect on SOD was found at the ratio of 24.74 % in compound 7.Key words: Aldose reductase, diabetes, inhibition, superoxide dismutase, TZD derivatives. Bazı kromonil-2,4-tiyazolidindiyon türevleri ile aldoz redüktaz ve süperoksit dismutaz aktivitelerindeki değişikliklerÖzet: Diabetes Mellitus (DM) hastalığındaki uzun süreli hiperglisemi nöropati, nefropati ve retinopati gibi geri-dönüşümsüz sekonder komplikasyonlara neden olmaktadır. Hiperglisemi sırasında polyol yolağının aktivitesi artmaktadır. Artan polyol yolağı aktivitesi ve aldoz redüktaz (AR) tarafından NADPH'ın aşırı tüketimi diğer homeostatik mekanizmaları etkilemektedir. AR'ın dahil olduğu hiperglisemiye bağlı kompleks metabolik değişiklikler ve oksidatif stres sonucunda oluşacak olan diyabetik komplikasyonların tedavisinde hem AR inhibitör etkisi olan hem de antioksidan özelliği bulunan dual etkili ajanların kullanılabilmesi olasılığı, araştırmalar ve tedavi açısından umut vericidir. Bunun yanısıra, klinik olarak denenmiş olan pekçok AR inhibitörünün (ARI) olumsuz farmakokinetikleri, toksik yan etkileri ve yetersiz etkileri nedeni ile ilaç adayı olarak yetersiz oldukları tespit edilmiştir. Bu nedenle, günümüzde hala yan etkisi az olan ARI leri üzerinde çalışmalar devam etmektedir. Çalışmamızda, AR enzimi sığır lenslerinden saflaştırılmıştır. Daha sonra, 17 farklı kromonil-2,4-tiyazolidindiyon türevlerinin AR ve süperoksit dismutaz (SOD) enzim aktiviteleri üzerine olası etkileri incelenmiştir. Sonuçlara göre; 1 ve 8 numaralı bileşikler en iyi ARI aktivitesini sırası i...

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“…Chromones considered a major class of the naturally occurring compounds. [2,3] Numerous biological activities have been attributed to chromone derivatives such as anticancer, [4] anti-HIV, [5] antiarrhythmic and hypotensive agents, [6] antioxidants agents, [7] antidiabetics agents, [8] antibacterial agents, [9] antifungal agents, [10] antiulcers agents, [11] anti-inflammatory agents, [12] antipsychosis agents, [13] immunostimulator agents, [14] antitubercular agents, [15] biocidal, [16] and treating wound. [17] Apigenin is a naturally occurring chromone that has been widely investigated for its anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

Abu‐Bakr

Khidre

Omar

et al. 2019

Journal of Heterocyclic Chem

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A series of furo[3,2-g]chromone derivatives were synthesized via the reaction of furochromone carbaldehyde 1 with amines 3a-d and thioglycolic acid to give thiazolidinones 4a-d. The later react with benzaldehyde/thiourea or hydroxylamine and DMF-DMA in glacial acetic acid to give thiazolopyrimidines 5a-d or thiazoloisoxazoles 6a-d, respectively. Also, the synthesis of α-aminophosphonates via the one-pot reaction of 1 and amines 3a,b were trapped by dialkylphosphites 7a-c afforded the corresponding αaminophosphonates 8a-f. Applying hexaalkyltriamidophosphites 9a,b to 1 gives alkylidenephosphorane ylides 11a,b in an open structure form. In the present investigation, the in vitro inhibition capacity of compounds (4a, 4c, 5b, 5c, 6b-d, 8a-f, and 11a) was screened in three human cancer cell lines HCT-116, MCF-7, and HepG2. The anticancer activity results revealed that 8b and 8e had more potent cytotoxic inhibition activity against HCT-116 cell line; however, all the tested compounds had obviously less cytotoxic activity against MCF-7 cell line, while 5b, 5c, and 6d were potent against HepG2 cell line compared with that of doxorubicin.

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Synthesis and antidiabetic activity of some new chromonyl-2,4-thiazolidinediones

Cited by 23 publications

References 20 publications

Studies on the antioxidant activities of some new chromone compounds

Studies on the antioxidant activities of some new chromone compounds

Alterations of aldose reductase and superoxide dismutase activities by some chromonyl-2, 4-thiazolidinedione derivatives

Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

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