Free-Radical Scavenging Activities of 2-Benzoxazolinone Derivatives Containing Thiosemicarbazide, Triazole, Thiadiazole and Hydrazone Units

Year 2011, Issue: 1, 27 - 50, 01.01.2011

Samiye Yabanoğlu Çiftci Nesrin Gökhan Kelekçi Umut Salgın Gökşen Gülberk Uçar

Abstract

It has been reported that some benzoxazolinone, triazole, thiadiazole and hydrazone derivatives showed significant analgesic and antiinflammatory activity. It has been speculated that non-steroidal antiinflammatory agents NSAIDs can act as the free radical scavengers and show antioxidant activity. It is also well documented that oxidative stres can play an important role in the side effects of many xenobiotics including NSAIDs. Therefore, in the present study, it was thought that the combination of different pharmacophores in one frame may lead to compounds with interesting pharmacological profiles and the effects of thiosemicarbazide, triazole, thiadiazole and hydrazone bearing 2-benzoxazolinone were investigated on free radical scavenging activity. Antioxidant activities of the novel compounds were evaluated by the determinations of 2,2-diphenyl-1-picrylhydrazyl DPPH radical scavenging activity, superoxide radical scavenging activity, hydrogen peroxide scavenging activity, nitric oxide scavenging activity and reducing power. The various antioxidant activities were compared to standard antioxidants such as butylated hydroxytoluen and ascorbic acid and the results were expressed as IC50 values. All of the newly synthesized compounds exhibited varying degrees of scavenging capacity on different active radicals; the compounds 13-18 hydrazone derivatives proved to be most active. Among those, compound 17 and 18, having p-methoxy and -hydroxyl groups on their phenyl rings, respectively showed the highest scavenging capacity of active radical species. These preliminary in vitro results may contribute to explain the potency of antiinflammatory activity of the compounds.

Keywords

Free-Radical Scavenging Activity, 2-Benzoxazolinone Derivatives, 2, 2-diphenyl-1-picrylhydrazyl, superoxide radical, hydrogen peroxide, nitric oxide

Tiyosemikarbazit, Triazol, Tiyadiazol ve Hidrazon içeren 2-Benzoksazolinon Türevlerinin Serbest Radikal Süpürme Aktiviteleri

Abstract

Bazı benzoksazolinonil triazol, tiyadiazol ve hidrazon türevlerinin belirgin analjezik ve antienflamatuar aktivite gösterdikleri rapor edilmiştir. Non steroidal antienflamatuar ajanların NSAIDler serbest radikal süpürücüleri olarak görev yaparak antioksidan aktivite gösterdikleri düşünülmüştür. Oksidatif stresin NSAIDler dahil bir çok ksenobiyotiğin yan etkilerinde önemli rol oynadığı açıkça belirlenmiştir. Dolayısıyla, bu çalışmada farklı farmakoforların kombinasyonlarının bir çerçevede toplanmasıyla ilginç farmakolojik profillere sahip bileşikler meydana gelebileceği düşünülmüş ve tiyosemikarbazit, triazol, tiyadiazol ve hidrazon taşıyan 2 benzoksazolinon türevlerinin serbest radikal süpürücü aktiviteleri incelenmiştir. Yeni sentezlenen bu türevlerin antioksidan aktiviteleri 2,2-difenil-1-pikrilhidrazil DPPH radikali, süperoksit radikali, hidrojen peroksit, nitrik oksit süpürücü aktivitelerinin ve indirgeyici güçlerinin belirlenmesiyle değerlendirilmiştir. Çeşitli antioksidan aktiviteler bütillenmiş hidroksitoluen ve askorbik asit gibi standart antioksidanlarla kıyaslanmış ve sonuçlar IC50 değeri şeklinde ifade edilmiştir. Yeni sentezlenen tüm bileşikler çeşitli derecelerde farklı aktif radikaller üzerinde süpürücü etki göstermişlerdir; bileşik 13-18’in hidrazon türevleri en aktif bileşikler olduğu saptanmıştır. Bunlar arasında fenil halkasında sırasıyla p-metoksi ve p-hidroksi grupları taşıyan bileşik 17 ve 18 aktif radikal türleri üzerinde en yüksek süpürme kapasitesine sahip oldukları saptanmıştır. Bu öncül in vitro sonuçlar bu bileşiklerin antienflamatuar aktivitelerinin derecelerini açıklamaya katkıda bulunmaktadır.

Keywords

Serbest radikal süpürücü aktivite, 2-benzoksazolinon türevleri, 2, 2-difenil-1-pikrilhidrazil, süperoksit radikali, hidrojen peroksit, nitrik oksit

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