Citation: Zahid Zaheer, Firoz A. Kalam Khan, Jaiprakash N. Sangshetti, Rajendra H. Patil. Expeditious synthesis, antileishmanial and antioxidant activities of novel 3-substituted-4-hydroxycoumarin derivatives[J]. Chinese Chemical Letters, ;2016, 27(02): 287-294. doi: 10.1016/j.cclet.2015.10.028 shu

Expeditious synthesis, antileishmanial and antioxidant activities of novel 3-substituted-4-hydroxycoumarin derivatives

a.
a. Dr. Rafiq Zakaria Campus, Y.B. Chavan College of Pharmacy, Aurangabad 431001, MS, India;
b.
b. Department of Biotechnology, Savitribai Phule Pune University, Pune 411007, MS, India

Corresponding author: Zahid Zaheer,
Received Date: 10 April 2015
Available Online: 31 July 2015

A series of novel 3-substituted-4-hydroxycoumarin derivatives 6(a-l) were synthesized in high yield using one-pot three component coupling reaction catalyzed by ceric ammonium nitrate. These compounds were evaluated for antileishmanial activity against Leishmania donovani promastigotes and antioxidant activity (DPPH-radical scavenging activity). Two compounds, 6h (IC₅₀ = 9.90 µmol/L) and 6i (IC₅₀ = 6.90 µmol/L) displayed potent antileishmanial activity when compared with standard antileishmanial agents pentamidine (IC₅₀ = 16.15 µmol/L) and miltefosine (IC₅₀ = 12.50 µmol/L). Three compounds, 6c (IC₅₀ = 10.79 µmol/L), 6h (IC₅₀ = 10.60 µmol/L), and 6i (IC₅₀ = 10.73 µmol/L) showed significant antioxidant activity favorably with the antioxidant standards butylated hydroxy toluene (IC₅₀ = 16.47 µmol/L) and ascorbic acid (IC₅₀ = 12.69 µmol/L). A molecular docking study of compounds 6(a-l) suggested a possible mode of binding with the Adenine phosphoribosyltransferase enzyme of L. donovani. ADME properties were predicted in silico and support the potential of 6(a-l) to show favorable drug-like properties.
- 4-Hydroxycoumarin,
- Ceric ammonium nitrate,
- Antileishmanial activity,
- Antioxidant activity,
- Molecular docking study,
- ADME properties
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