Semi-Synthesis, Antibacterial, Anticholinesterase Activities, and Drug Likeness Properties of New Analogues of Coumarins
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ORIGINAL ARTICLE
Semi‑Synthesis, Antibacterial, Anticholinesterase Activities, and Drug Likeness Properties of New Analogues of Coumarins Isolated from Ferula lutea (Poir.) Maire Mansour Znati1 · Afifa Zardi‑Bergaoui1 · Mejda Daami‑Remadi2 · H. Ben Jannet1 Received: 14 February 2020 / Accepted: 13 May 2020 © The Tunisian Chemical Society and Springer Nature Switzerland AG 2020
Abstract This work describes the valorization of two natural bioactive coumarins via the semi-synthesis of new derivatives and the study of their antibacterial and anticholinesterase potentials. Marmesin 1 and Scopoletin 2 were isolated from the dichloromethane extract of Ferula lutea (Poir.) Maire roots. Esterification of 1 with a series of acid chlorides, led to the formation of esters 1′a-j. The O-propargylated intermediate 3 was used as dipolarophile affording via 1,3-dipolar cycloaddition the isoxazole-linked coumarins 3′a-f. The study of the antibacterial activity of all the prepared compounds showed that S. aureus and E. faecalis are sensitive towards the ester 1′c and the isoxazole 3′c (MIC = 62.0 µg/mL). Compound 3′b displayed the highest antibacterial effect against all the tested strains (MIC = 62.0 µg/mL). The ester 1′j exhibited the highest anticholinesterase effect (IC50 = 98.0 µg/mL). The drug likeness scores was calculated using Molinspiration software and discussed. Keywords Ferula lutea · Coumarins · Esters · Isoxazoles · Biological activities · Drug likeness properties
1 Introduction Antibiotic resistance is a serious health problem which requires the development of new therapeutics and antimicrobial strategies [1]. Furthermore, Alzheimer’s disease is a progressive pathology which affects the nervous system and characterized by cholinergic deficit. People with Alzheimer’s disease have decreased levels of choline in brain areas that control learning, memory, behavior and emotional responses [2]. Coumarins, one of the main families of natural secondary metabolites, constitute a potential class of promising antibacterial and anti-Alzheimer’s agents [2, 3]. * H. Ben Jannet [email protected] 1
Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Team: Medicinal Chemistry and Natural Products (LR11ES39), Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019 Monastir, Tunisia
UR13AGR09, Integrated Horticultural Production in the Eastern Center of Tunisia, Regional Center for Research in Horticulture and Biological Agriculture of Chott‑Mariem, University of Sousse, 4042 Chott‑Mariem, Tunisia
2
Coumarins (1,2-benzopyrone) are a class of phytochemicals compounds with phototoxic properties as a natural chemical defense against insects, bacteria and fungi [4, 5]. Coumarin/furanocoumarins occupy a special position among these compounds and they represent important building blocks in bioactive compounds, which show many biological and pharmacological effects [6] such as anticoagulant [7], antioxidant [7], anti-inflammatory [7], antiallergic [8], anti-cancer activities
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