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

Year 2019, Volume: 14 Issue: 2, 296 - 315, 30.11.2019

Aliye Gediz Ertürk

https://doi.org/10.29233/sdufeffd.572188

Abstract

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

Supporting Institution

Ordu University Scientific Research Projects Coordination Department (ODU-BAP)

Project Number

HD-1709

Thanks

This research was funded by Ordu University Scientific Research Projects Coordination Department (ODU-BAP) under financial support (No. HD-1709).

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

Abstract

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.

Keywords

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

Project Number

HD-1709

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