Drug Res (Stuttg) 2018; 68(07): 378-386
DOI: 10.1055/s-0043-123998
Original Article
© Georg Thieme Verlag KG Stuttgart · New York

Synthesis and Molecular Docking Studies of (E)-4-(Substituted-benzylideneamino)-2H-Chromen-2-one Derivatives: Entry to New Carbonic Anhydrase Class Of Inhibitors

Tanzeela Abdul Fattah
1   Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan
,
Aamer Saeed
1   Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan
,
Pervaiz Ali Channar
1   Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan
,
Fayaz Ali Larik
1   Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan
,
Mubashir Hassan
2   Department of Biological Sciences, College of Natural Sciences, Kongju National University, Gongju, Chungnam, Republic of Korea
,
Hussain Raza
2   Department of Biological Sciences, College of Natural Sciences, Kongju National University, Gongju, Chungnam, Republic of Korea
,
Qamar Abbas
3   Department of Physiology, University of Sindh, Jamshoro, Pakistan
,
Sung-Yum Seo
2   Department of Biological Sciences, College of Natural Sciences, Kongju National University, Gongju, Chungnam, Republic of Korea
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 03. Oktober 2017

accepted 16. November 2017

Publikationsdatum:
12. Februar 2018 (online)

Abstract

The present article illustrated the synthesis and characterization of a novel series of (E)-4-(substituted-benzylideneamino)-2H-chromen-2-one derivatives 4a-4j in good to excellent yields. The target compounds were synthesized by refluxing 4-aminocoumarin with aromatic aldehydes in ethanol. The structural confirmation was achieved by spectroscopic techniques such as (1H, 13C-NMR and FT-IR) and elemental analysis. The synthesized compounds were evaluated for carbonic anhydrase II (CA-II) inhibition and free radical scavenging activity. All the compounds showed CA-II inhibition in the micro molar range. The compound 4c exhibited higher potential in the series with IC50=0.0928±0.00545 µM (standard Acetazolamide IC50=0.997±0.0586 µM). Pharmacological investigations showed that the synthesized compounds 4a-4j obey Lipinsk’s rule. Compound 4c elicited drug likeness and showed drug score value of 0.05. Molecular docking analysis showed that compound 4c interacts with Asn66 and Gln91 amino acid residues. [Graphical Abstract].

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Graphical Abstract

Supporting Information

 
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