Synthesis of New Benzenesulfonamides and Benzamides, Investigation of Carbonic Anhydrase and Cholinergic Effects

Öz

In this study, new benzene sulfonamide and benzamide derivatives were synthesized from 1-bromo-2,4-dimethoxybenzene (8) and 1-bromo-3,5-dimethoxybenzene (10). Inhibitory effects of synthesized compounds on hCA-I, hCA-II, AChE and BChE enzymes were investigated. The synthesis of the new amide derivatives 9 and 11 was carried out from the reaction of the starting compounds 8 and 10 with CSI. Treatment of methoxy-substituted benzenes with excess HSO3Cl followed by reaction of the resulting benzene sulfonyl chlorides with ammonia gave sulfonamides 16 and 17. It was determined that the synthesized sulfonamide and benzamide derivatives showed inhibition effect on hCA-I, hCA-II, AChE and BChE enzymes at micromolar level.

Anahtar Kelimeler

• Benzenesulfonamide
• Benzamide
• Carbonic Anhydrase
• Anti-Alzheimer

Proje Numarası

Proje No: MARŞL.21.01

Yeni Benzensülfonamitler ve Benzamitlerin Sentezi, Karbonik Anhidraz ve Kolinerjik Etkilerinin İncelenmesi

Öz

Bu çalışmada, 1-brom-2,4-dimetoksibenzen (8) ve 1-brom-3,5-dimetoksibenzen (10)’dan çıkılarak yeni benzensülfonamit ve benzamit türevleri sentezlendi. Sentezlenen bileşiklerin hCA-I, hCA-II, AChE ve BChE enzimleri üzerine inhibisyon aktiviteleri araştırıldı. Yeni amit türevleri 9 ve 11’in sentezi çıkış bileşikleri 8 ve 10’un CSI ile olan reaksiyonundan gerçekleştirildi. Metoksi substitue benzenlerin aşırı HSO3Cl ile muamelesi, akabinde elde edilen benzen sülfonil klorürlerin amonyakla reaksiyonu sülfonamitler 16 ve 17’yi verdi. Sentezi gerçekleştirilen sülfonamit ve benzamit türevlerinin hCA-I, hCA-II, AChE ve BChE enzimleri üzerine mikromolar seviyede inhibisyon etkisi gösterdikleri belirlenmiş oldu.

Anahtar Kelimeler

• Benzen sülfonamit
• Benzamit
• Karbonik Anhidraz
• Anti-Alzheimer

Destekleyen Kurum

Ağrı İbrahim Çeçen Üniversitesi Bilimsel Araştırma Projeleri Koordinatörlüğü

Proje Numarası

Proje No: MARŞL.21.01

Teşekkür

Projeyi maddi olarak destekleyen Ağrı İbrahim Çeçen Üniversitesi BAP Koordinatörlüğüne (Proje No: MARŞL.21.01) ve çalışmanın gerçekleştirildiği Ağrı İbrahim Çeçen Üniversitesi Merkezi Araştırma ve Uygulama Laboratuvarına teşekkür ederim. Biyokimya çalışmaları boyunca bilgi ve deneyiminden faydalandığım Prof. Dr. Hülya AKINCIOĞLU’na teşekkürü bir borç bilirim.

Kaynakça

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