INVESTIGATION OF ANTIOXIDANT AND ANTI-ALZHEIMER PROPERTIES OF NOVEL 4-AMINOANTIPYRINE-DERIVED SCHIFF BASES

Ercan Çınar

Makale detayları

INVESTIGATION OF ANTIOXIDANT AND ANTI-ALZHEIMER PROPERTIES OF NOVEL 4-AMINOANTIPYRINE-DERIVED SCHIFF BASES

Yazarlar:

Ercan Çınar

Yayıncı:

Inonu University

Ana Başlıklar:

Halk Sağlığı (Diğer)

Dergi:

İnönü Üniversitesi Sağlık Hizmetleri Meslek Yüksek Okulu Dergisi Vol.13 Issue 3, pp.707-722

Belge Tipi:

Makale

Yayın Tarihi:

10/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001359990

pISSN:

2147-7892

Anahtar kelimeler:

Özet:

 In this study, Schiff bases derived from 4-aminoantipyrine 4AAP were synthesized and elucidated using spectroscopic methods ¹H- and ¹³C-NMR. DPPH 1,1-diphenyl-2-picrylhydrazyl free radical scavenging test, 2,2-azino-bis3-ethylbenzothiazoline-6-sulfonic acid ABTS radical scavenging activity, and copper ion reducing antioxidant capacity CUPRAC analysis were used to evaluate Schiff bases antioxidant potentials. Furthermore, their inhibitory potentials against cholinesterase ChE enzymes were investigated. The compound 4E-4-5-chloro-2-hydroxybenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R3 exhibited a higher inhibition effect with an inhibitory value of 27.05  0.13 µM as compared to the standard inhibitor neostigmine 33.3  0.32 µM. The synthesized compounds were subjected to antioxidant tests, including DPPH, ABTS, and CUPRAC, respectively. In the DPPH experiment, the compound 4E-4-2-hydroxy-5-nitrobenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R5 exhibited activity with a value of 116.79  2.73 µM. However, in this test, all compounds showed lower antioxidant activity as compared to standard antioxidants such as butylated hydroxyanisole BHA, butylated hydroxytoluene BHT, and α-tocopherol α-TOC. By contrast, in the ABTS assay, all compounds were active as compared to standard antioxidants, and the R3 compound showed high antioxidant activity. In the CUPRAC experiment, although the compounds showed antioxidant activity, it was not as high as that of the standard antioxidants. 4E -4-2-hydroxybenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R1 compound was the most effective in the CUPRAC method.

 In this study, Schiff bases derived from 4-aminoantipyrine 4AAP were synthesized and elucidated using spectroscopic methods ¹H- and ¹³C-NMR. DPPH 1,1-diphenyl-2-picrylhydrazyl free radical scavenging test, 2,2-azino-bis3-ethylbenzothiazoline-6-sulfonic acid ABTS radical scavenging activity, and copper ion reducing antioxidant capacity CUPRAC analysis were used to evaluate Schiff bases antioxidant potentials. Furthermore, their inhibitory potentials against cholinesterase ChE enzymes were investigated. The compound 4E-4-5-chloro-2-hydroxybenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R3 exhibited a higher inhibition effect with an inhibitory value of 27.05  0.13 µM as compared to the standard inhibitor neostigmine 33.3  0.32 µM. The synthesized compounds were subjected to antioxidant tests, including DPPH, ABTS, and CUPRAC, respectively. In the DPPH experiment, the compound 4E-4-2-hydroxy-5-nitrobenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R5 exhibited activity with a value of 116.79  2.73 µM. However, in this test, all compounds showed lower antioxidant activity as compared to standard antioxidants such as butylated hydroxyanisole BHA, butylated hydroxytoluene BHT, and α-tocopherol α-TOC. By contrast, in the ABTS assay, all compounds were active as compared to standard antioxidants, and the R3 compound showed high antioxidant activity. In the CUPRAC experiment, although the compounds showed antioxidant activity, it was not as high as that of the standard antioxidants. 4E -4-2-hydroxybenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R1 compound was the most effective in the CUPRAC method.

 In this study, Schiff bases derived from 4-aminoantipyrine 4AAP were synthesized and elucidated using spectroscopic methods ¹H- and ¹³C-NMR. DPPH 1,1-diphenyl-2-picrylhydrazyl free radical scavenging test, 2,2-azino-bis3-ethylbenzothiazoline-6-sulfonic acid ABTS radical scavenging activity, and copper ion reducing antioxidant capacity CUPRAC analysis were used to evaluate Schiff bases antioxidant potentials. Furthermore, their inhibitory potentials against cholinesterase ChE enzymes were investigated. The compound 4E-4-5-chloro-2-hydroxybenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R3 exhibited a higher inhibition effect with an inhibitory value of 27.05  0.13 µM as compared to the standard inhibitor neostigmine 33.3  0.32 µM. The synthesized compounds were subjected to antioxidant tests, including DPPH, ABTS, and CUPRAC, respectively. In the DPPH experiment, the compound 4E-4-2-hydroxy-5-nitrobenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R5 exhibited activity with a value of 116.79  2.73 µM. However, in this test, all compounds showed lower antioxidant activity as compared to standard antioxidants such as butylated hydroxyanisole BHA, butylated hydroxytoluene BHT, and α-tocopherol α-TOC. By contrast, in the ABTS assay, all compounds were active as compared to standard antioxidants, and the R3 compound showed high antioxidant activity. In the CUPRAC experiment, although the compounds showed antioxidant activity, it was not as high as that of the standard antioxidants. 4E -4-2-hydroxybenzylideneamino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one R1 compound was the most effective in the CUPRAC method.

 Bu çalışmada, 4-aminoantipirin4AAP türevi Schiff bazları sentezlendi ve bu moleküllerin yapıları spektroskopik yöntemlerle 1H- ve 13C-NMR aydınlatıldı. Literatürde ilk kez sentezlenen bu moleküllerin antioksidan potansiyelleri, DPPH- 1,1-difenil-2-pikrilhidrazil serbest radikal süpürücü etkisi, 2,2-azino-bis3-etilbenztiazolin-6-sülfonik asit ABTS radikal süpürücü aktivitesi ve bakır iyon indirgeyici antioksidan kapasitesi CUPRAC analizi ile araştırıldı. Daha sonra kolinesterazlara ChE karşı inhibitör potansiyelleri incelendi. Enzim inhibisyon çalışmalarında, 4E-4-5-kloro-2-hidroksibenzilidenamino-1,2-dihidro-2,3-dimetil-1-fenilpirazol-5-on R3 bileşikleri, 27,050,13 µM inhibisyon değeriyle, standart inhibitör Neostigminin 33,3  0,32 µM değerine kıyasla daha yüksek bir inhibisyon etkisi gösterdi. Daha sonra antioksidan yöntemler DPPH, ABTS ve CUPRAC analiz edildi. DPPH testinde, 4E-4-2-hidroksi-5-nitrobenzilidenamino-1,2-dihidro-2,3-dimetil-1-fenilpirazol-5-on R5 molekülü, 116,792,73 µM ile en iyi aktiviteyi gösterdi. Ancak bu deney yönteminde tüm moleküller standart antioksidanlardan bütilhidroksianisol BHA, bütillenmiş hidroksitoluen BHT ve alfa-tokoferol α-TOC daha iyi sonuçlar vermedi. ABTS yönteminde sentezlenen tüm moleküller standart antioksidanlar BHA ve α-TOC ile karşılaştırıldığında iyi aktivite gösterdi. R3 molekülü en iyi aktiviteyi gösterdi. CUPRAC yönteminde ise tüm moleküller antioksidan aktivite göstermesine rağmen standart antioksidanlar kadar iyi değildi. 4E-4-2-hidroksibenzilidenamino-1,2-dihidro-2,3-dimetil-1-fenilpirazol-5-on R1 molekülü aktif molekül olarak en iyi aktiviteyi gösterdi.

Makale detayları

INVESTIGATION OF ANTIOXIDANT AND ANTI-ALZHEIMER PROPERTIES OF NOVEL 4-AMINOANTIPYRINE-DERIVED SCHIFF BASES

Yazarlar:

Ercan Çınar

Yayıncı:

Inonu University

Ana Başlıklar:

Halk Sağlığı (Diğer)

Dergi:

İnönü Üniversitesi Sağlık Hizmetleri Meslek Yüksek Okulu Dergisi Vol.13 Issue 3, pp.707-722

Belge Tipi:

Makale

Yayın Tarihi:

10/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001359990

pISSN:

2147-7892

Alzheimer disease

4-Aminoantipyrine

Antioxidants

Schiff base4-aminoantipirin

Alzheimer hastalığı

Antioksidanlar

Schiff bazı

Sayı

Makale detayları

Yazarlar: Ercan Çınar

Yayıncı: Inonu University

Ana Başlıklar: Halk Sağlığı (Diğer)

Dergi: İnönü Üniversitesi Sağlık Hizmetleri Meslek Yüksek Okulu Dergisi Vol.13 Issue 3, pp.707-722

Belge Tipi: Makale

Yayın Tarihi: 10/2025

Belge Dili: İngilizce

Document ID (Org No.): 2001359990

pISSN: 2147-7892

Sayı

Yazarlar:

Ercan Çınar

Yayıncı:

Inonu University

Ana Başlıklar:

Halk Sağlığı (Diğer)

Dergi:

İnönü Üniversitesi Sağlık Hizmetleri Meslek Yüksek Okulu Dergisi Vol.13 Issue 3, pp.707-722

Belge Tipi:

Makale

Yayın Tarihi:

10/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001359990

pISSN:

2147-7892