Antileishmanial activity of novel indolyl-coumarin hybrids: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction.

Journal: Bioorganic & medicinal chemistry letters
PMID:

Abstract

In present work we have designed and synthesized total twelve novel 3-(3-(1H-indol-3-yl)-3-phenylpropanoyl)-4-hydroxy-2H-chromen-2-one derivatives 13(a-l) using Ho(3+) doped CoFe2O4 nanoparticles as catalyst and evaluated for their potential antileishmanial and antioxidant activities. The compounds 13a, 13d and 13h were found to possess significant antileishmanial activity (IC50 value=95.50, 95.00 and 99.00μg/mL, respectively) when compared to the standard sodium stibogluconate (IC50=490.00 μg/mL). The compounds 13a (IC50=12.40 μg/mL), 13d (IC50=13.49 μg/mL), 13g (IC50=13.24 μg/mL) and 13l (IC50=13.74 μg/mL) had shown good antioxidant activity when compared with standards butylated hydroxy toluene (IC50=16.5 μg/mL) and ascorbic acid (IC50=12.8 μg/mL). After performing molecular docking studies, it was found that compounds 13a and 13d had potential to inhibit pteridine reductase 1 enzyme. In silico ADME pharmacokinetic parameters had shown promising results and none of the synthesized compounds had violated Lipinski's rule of five. Thus, suggesting that compounds from the present series can serve as important gateway for the design and development of new antileishmanial as well as antioxidant agent.

Authors

  • Jaiprakash N Sangshetti
    Department of Pharmaceutical Chemistry, Y. B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Aurangabad 431 001(MS), India.
  • Firoz A Kalam Khan
    Dr. Rafiq Zakaria Campus, Y.B. Chavan College of Pharmacy, Aurangabad 431001, (M.S.), India.
  • Abhishek A Kulkarni
    Dr. Rafiq Zakaria Campus, Y.B. Chavan College of Pharmacy, Aurangabad 431001, (M.S.), India.
  • Rajendra H Patil
    Department of Biotechnology, Savitribai Phule Pune University, Pune 411007, (MS), India.
  • Amol M Pachpinde
    Department of Chemistry, Jawahar Art Science and Commerce College, Andur, Osmanabad 413603, (M.S.), India.
  • Kishan S Lohar
    Materials Research Laboratory, Srikrishna Mahavidyalaya Gunjoti, Omerga, Osmanabad 413 613, (M.S.), India.
  • Devanand B Shinde
    Shivaji University, Vidyanagar, Kolhapur 416 004, (M.S.), India.