4-Aminoantipirin İçeren Yeni Bir Schiff Baz Üzerine Sentetik, Spektroskopik, Teorik ve Biyolojik Açıdan Bir İnceleme

4-Aminoantipirin ile bifenil karboksaldehitten yeni bir Schiff bazı olan 4-(([1,1'-bifenil]-4-ilmetilen)amino)-1,5-dimetil-2-fenil-1,2-dihidro-3H-pirazol-3-on (BiPhAAP) sentezlendi ve elementel analiz, FT-IR ve 1H ve 13C NMR spektroskopik metotları kullanılarak karakterize edildi. Spektroskopik bulgulara ek olarak, geometrik tanımlar ve bileşikteki yüzey etkileşimlerinin kapsamı X-ışını kristalografik ve Moleküler Hirshfeld yüzey (MHS) analizi teknikleriyle belirlenmiştir. Deneysel ve hesaplanan FT-IR sonuçları arasındaki farklar kristal yapısında molekül içi (C-H….O tipi) hidrojen bağlarının varlığını kanıtlamıştır. İki Gram negatif (Escherichia coli ve Proteus vulgaris) ve iki Gram pozitif (Bacillus subtilis ve Micrococcus luteus) bakteri suşu ve üç maya suşuna (Candida albicans, Aspergillus niger ve Candida globra) karşı çalışılan in vitro antimikrobiyal potansiyel 250, 125 ve 62.5 mg/mL konsantrasyonlarda agar well difüzyon metodu kullanılarak incelenmiştir. Bu bileşiğin in vitro antioksidan aktiviteleri, beş farklı antioksidan testi (DPPH radikal süpürme, indirgeme gücü, metal şelatlama etkinliği, süperoksit temizleme ve toplam antioksidan) ile hesaplandı. Yeni bileşiğin sitotoksik aktivitesi, insan meme kanseri hücrelerine (MCF-7) karşı araştırıldı. IC50 değerleri ise, MTT testine göre belirlendi.

Anahtar Kelimeler:

4-Aminoantipirin, Antimikrobiyal aktivite, Antioksidan aktivite, MTT testi, Teorik çalışma

A Synthetic, Spectroscopic, Theoretical and Biological Perspective on a Novel Schiff Base Included 4-Aminoantipyrine

A novel Schiff base, 4-(([1,1'-biphenyl]-4-ylmethylene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (BiPhAAP), obtained from biphenyl carboxaldehyde with 4-aminoantipyrine was characterized using elemental analysis, FT-IR, and 1H and 13C NMR spectroscopic methods. In addition to the spectroscopic findings, geometrical descriptions and the extent of surface interactions in the compound were determined by X-ray single crystallographic and Molecular Hirshfeld surface (MHS) analysis techniques. The distinctions between experimental and calculated FT-IR results have proved the presence of intra-molecular (C–H….O type) hydrogen bonds in the crystal structure. The in vitro antimicrobial potential, which was studied against two Gram-negative (Escherichia coli and Proteus vulgaris) and two Gram-positive (Bacillus subtilis and Micrococcus luteus) bacterial strains, and three yeast strains (Candida albicans, Aspergillus niger and Candida globrata) was examined by using the agar well diffusion method at concentrations of 250, 125 and 62.5 mg/mL. The in vitro antioxidant activities of this compound were estimated by five different antioxidant assays (DPPH radical scavenging, reducing power, metal chelating activity, superoxide scavenging, and total antioxidant). Cytotoxic activity of the new compound was sought against human breast carcinoma cells (MCF-7). The IC50 values were established with respect to the MTT test.

Keywords:

4-Aminoantipyrine, Antimicrobial activity, Antioxidant activity, MTT assay, Theoretical study,

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