(2R,4aS,6aS,12bR,14aS,14bR)10-Hydroxy-N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxamide
Author:
Xie Yuhan1,
Kuan Houin1,
Wei Qin1,
Gianoncelli Alessandra2ORCID,
Ribaudo Giovanni2ORCID,
Coghi Paolo13
Affiliation:
1. School of Pharmacy, Macau University of Science and Technology, Macau 999078, China
2. Department of Molecular and Translational Medicine, University of Brescia, 25123 Brescia, Italy
3. State Key Laboratory of Quality Research in Chinese Medicine, Science and Technology Building, Macau University of Science and Technology, Avenida Wai Long, Taipa, Macau 999078, China
Abstract
We herein report the synthesis of a derivative of the natural compound celastrol linked to the antimalarial drug primaquine through an amide obtained by the activation of the carboxylic acid with HOBt/EDC. The chemical structure of the new molecule was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), correlation spectroscopy (1H-1H-COSY), distortionless enhancement by polarization transfer (DEPT), mass spectrometry, Fourier-transform infrared (FTIR), and ultraviolet (UV) spectroscopies. Computational studies were enrolled to predict the interaction of the synthesized compound with sarco-endoplasmic reticulum (SR) Ca2+ transport ATPase (SERCA), a target of relevance for developing new therapeutics against arthritis. The drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties.
Funder
Macao University of Science and Technology
Subject
Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry