Effective Synthesis and Characterization of Bis(Sulfonamide) Containing Chalcone

Öz

In this study, new chalcone derivatives containing sulfonamide were synthesized rapidly and efficiently. The synthesis of the chalcone skeletal structure was performed using the base-catalyzed Claisen-Schmidt condensation reaction method. Chalcone 3 was synthesized with 80% yield as a result of the reaction of 4-methoxy acetophenone, 4-nitrobenzaldehyde and NaOH. Reduction of the nitro functional group in compound 1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (3) with SnCl2.2H2O obtained the target compound 3-(4-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (4) in 98% yield. The synthesis of target molecules that has the potential to be used in many different therapeutic applications, including Alzheimer's disease, has been successfully achieved as a result of the reaction of amine (4) with 3-(trifluoromethyl)benzenesulfonyl chloride, 4-fluorobenzenesulfonyl chloride, 4-methoxybenzenesulfonyl chloride, naphthalene-1-sulfonyl chloride, pyridine-3-sulfonyl chloride and methanesulfonyl chloride.

Anahtar Kelimeler

• Sulfonamide
• Chalcone
• Claisen-Schmidt Reaction

Bis(Sülfonamid) İhtiva Eden Kalkon Türevlerinin Etkin Bir Şekilde Sentezi ve Karakterizasyonu

Öz

Bu çalışmada, sülfonamid içeren yeni kalkon türevleri hızlı ve etkili bir şekilde sentezlendi. Kalkon iskelet yapısının sentezi, baz katalize Claisen-Schmidt kondenzasyon reaksiyon yöntemi kullanılarak yapıldı. 4-metoksi asetofenon, 4-nitrobenzaldehit ve NaOH’in reaksiyonu sonucu 3 nolu kalkon %80 verimle sentezlendi. Elde edilen 1-(4-metoksifenil)-3-(4-nitrofenil)prop-2-en-1-on (3) bileşiğindeki, nitro fonksiyonel grubunun SnCl2.2H2O ile indirgenmesiyle hedef bileşik 3-(4-aminofenil)-1-(4-metoksifenil)prop-2-en-1-on (4) %98 verimle elde edildi. Aminin (4), 3-(triflorometil)benzensülfonil klorür, 4-florobenzensülfonil klorür, 4-metoksibenzensülfonil klorür, naftalen-1-sülfonil klorür, pridin-3-sülfonil klorür ve metansülfonil klorür ile reaksiyonu sonucu Alzheimer hastalığı başta olmak üzere birçok farklı terapötik uygulamada kullanılabilme potansiyeline sahip olan moleküllerin sentezi başarılı bir şekilde gerçekleştirildi.

Anahtar Kelimeler

• Sülfonamid
• Kalkon
• Claisen-Schmidt Reaksiyonu

Kaynakça

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