(Z)- and (E)-5-Arylmethylenehydantoins: spectroscopic properties and configuration assignment

Tan, Siong Kiat; Ang, Kok-Peng; Fong, Y.-F.

doi:10.1039/p29860001941

Cited by 66 publications

(29 citation statements)

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“…However according to the literature, the arylidenethiazolidinediones were in the Z configuration [13][14][15]. In this study, only one isomer was obtained.…”

Section: Resultsmentioning

confidence: 98%

Synthesis of New 3‐(Substituted Phenacyl)‐5‐[3′‐(4H‐4‐oxo‐1‐benzopyran‐2‐yl)‐benzylidene]‐2,4‐thiazolidinediones and their Antimicrobial Activity

Tunçbìlek¹,

Altanlar

2006

Archiv der Pharmazie

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Synthesis of 3-(3-nitrophenacyl)thiazolidine-2,4-dione 2g and 3-(substituted phenacyl)-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)-benzylidene]-2,4-thiazolidinediones 4a-g are reported in this paper. These compounds 4a-g were prepared from 3'-flavone carboxaldehyde and 3-substituted phenacyl-2,4-thiazolidinediones using Knoevenagel reaction. The structures of all compounds were confirmed by IR, 1H-NMR, mass spectral data, and elemental analyses. The molecules 4a-g were evaluated for in-vitro antimicrobial activity against Staphylococcus aureus, Candida albicans, Candida krusei, Candida glabrata, and Candida parapsilosis. Compounds 4c and 4f showed better inhibitory activity when compared to fluconazole against Candida krusei and Candida glabrata.

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“…However according to the literature, the arylidenethiazolidinediones were in the Z configuration [13][14][15]. In this study, only one isomer was obtained.…”

Section: Resultsmentioning

confidence: 98%

Synthesis of New 3‐(Substituted Phenacyl)‐5‐[3′‐(4H‐4‐oxo‐1‐benzopyran‐2‐yl)‐benzylidene]‐2,4‐thiazolidinediones and their Antimicrobial Activity

Tunçbìlek¹,

Altanlar

2006

Archiv der Pharmazie

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“…In these compounds, 2,4-thiazolidinedione/2,4-imidazolidinedione/2-thioxo-imidazolidine-4-one rings are linked to 2 nd or 3 rd positions of chromen ring. In the literature it was reported that in reactions using unsubstituted imidazolidinediones and benzaldehydes or 3-substituted thiazolidinedione and 3-formyl chromone in an acidic medium, the main product was the Z isomer (15,18). The coupled 13 C NMR study of arylidene thiazolidinediones and imidazolidinediones also showed that only the Z isomer was formed (1,19).…”

Section: Resultsmentioning

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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“…In mass spectra, the compounds had an M + H ion peak. In the literature it was reported that in reactions using unsubstituted imidazolidinediones and benzaldehydes or 3-substituted thiazolidinedione and 3-formyl chromone in an acidic medium, the main product was the Z isomer 16,17 . The coupled 13 C NMR study of arylidene thiazolidinediones and imidazolidinediones also showed that only the Z isomer was formed 18,19 .…”

Section: Resultsmentioning

confidence: 99%

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

Ceylan–Ünlüsoy

Verspohl

Ertan

2010

Journal of Enzyme Inhibition and Medicinal Chemistry

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(Z)- and (E)-5-Arylmethylenehydantoins: spectroscopic properties and configuration assignment

Cited by 66 publications

References 0 publications

Synthesis of New 3‐(Substituted Phenacyl)‐5‐[3′‐(4H‐4‐oxo‐1‐benzopyran‐2‐yl)‐benzylidene]‐2,4‐thiazolidinediones and their Antimicrobial Activity

Synthesis of New 3‐(Substituted Phenacyl)‐5‐[3′‐(4H‐4‐oxo‐1‐benzopyran‐2‐yl)‐benzylidene]‐2,4‐thiazolidinediones and their Antimicrobial Activity

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

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

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