Synthesis and cytotoxic evaluation of monocarbonyl curcuminoids and their pyrazoline derivatives

• Published in: Monatshefte für Chemie Vol. 150; no. 12; pp. 2045 - 2051
• Main Authors: Van de Walle, Tim, Theppawong, Atiruj, Grootaert, Charlotte, De Jonghe, Steven, Persoons, Leentje, Daelemans, Dirk, Van Hecke, Kristof, Van Camp, John, D’hooghe, Matthias
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01-12-2019; Springer Nature B.V
• Subjects: Analytical Chemistry; Animal behavior; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Cytotoxicity; Derivatives; Inorganic Chemistry; Organic Chemistry; Original Paper; Physical Chemistry; Theoretical and Computational Chemistry; Heterocycles; Real-time proliferation assay; Curcumin; Antitumor agents; Aldol reactions
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-019-02516-1

A small set of structurally different monocarbonyl curcuminoids was prepared and screened for cytotoxic activity. In particular, bis-3-methoxy-4-hydroxy- and bis-4-methoxyphenyl-substituted monocarbonyls were synthesized and transformed into the corresponding three-dimensional
N
-acetylpyrazoline derivatives. In addition, a non-symmetrical indole-based monocarbonyl curcumin was prepared as well. Preliminary cytotoxic evaluation revealed significant effects for 4-hydroxy (pyrazoline) monocarbonyl curcuminoids, whereas the non-phenolic variants displayed rather poor activity.
Graphic abstract