ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and anti-plasmodial activity of isoandrographolide acetals

Nitesh Tamang, Sai Kiran Mavileti, Mamta Yadav, Srinivas Nanduri, Dinkar Sahal, and Nageswara Rao Golakoti

Department of Chemistry, Sri Sathya Sai Institute of Higher Learning, Puttaparthi, India

E-mail: dsahal@gmail.com

Received: 17 August 2022  Accepted: 18 January 2023

Abstract:

Isoandrographolide (2) and its nineteen acetals (3a–3o, 4, 5 and 6a–6b) of which fifteen are new were synthesized and characterized using ¹H-NMR, ¹³C-NMR, mass spectrometry, and IR spectroscopy. The compound 3c was characterized using single-crystal X-ray diffraction as well. All the compounds were tested for their anti-plasmodial potencies (IC₅₀) against the Chloroquine sensitive Pf3D7 and chloroquine resistant PfINDO strains. Potent compounds were further tested also for their cytotoxicity (CC₅₀) against mammalian cells. Compounds 3d (IC₅₀ 10.59 µM) and 3e (IC₅₀ 12.83 µM) were found to be the most active with mammalian cell CC₅₀ > 100 µM for both the compounds.

Graphical abstract

Keywords: Isoandrographolide; Acetals of isoandrographolide; Semi-synthesis; Malaria; Anti-plasmodial activity; Cytotoxicity

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02684-9

Chemical Papers 77 (6) 3015–3023 (2023)