Two conformationally constrained compounds similar to chicoric acid but lacking the catechol and carboxyl groups were prepared. In these analogues, the single bond between the two caffeoyl fragments has been replaced with a chiral oxirane ring and both aromatic residues modified protecting completely or partially the catechol moiety as methyl ether. Preliminary molecular modelling studies carried out on the two analogues showed interactions near the active site of HIV integrase; however, in comparison with raltegravir, the biological evaluation confirmed that CAA-1 and CAA-2 were unable to inhibit infection at lower concentration.

Righi, G., Pelagalli, R., Isoni, V., Tirotta, I., Dallocchio, R., Dessì, A., et al. (2017). Synthesis, molecular modeling and biological evaluation of two new chicoric acid analogs. NATURAL PRODUCT RESEARCH, 31(4), 397-403 [10.1080/14786419.2016.1169413].

Synthesis, molecular modeling and biological evaluation of two new chicoric acid analogs

MACCHI, BEATRICE;
2017-02-01

Abstract

Two conformationally constrained compounds similar to chicoric acid but lacking the catechol and carboxyl groups were prepared. In these analogues, the single bond between the two caffeoyl fragments has been replaced with a chiral oxirane ring and both aromatic residues modified protecting completely or partially the catechol moiety as methyl ether. Preliminary molecular modelling studies carried out on the two analogues showed interactions near the active site of HIV integrase; however, in comparison with raltegravir, the biological evaluation confirmed that CAA-1 and CAA-2 were unable to inhibit infection at lower concentration.
feb-2017
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore BIO/14 - FARMACOLOGIA
Settore CHIM/08 - CHIMICA FARMACEUTICA
English
Con Impact Factor ISI
analogues; chicoric acid; HIV integrase; inhibitors; Plant Science; Biochemistry; Analytical Chemistry; Organic Chemistry
www.tandf.co.uk/journals/titles/14786419.asp
Righi, G., Pelagalli, R., Isoni, V., Tirotta, I., Dallocchio, R., Dessì, A., et al. (2017). Synthesis, molecular modeling and biological evaluation of two new chicoric acid analogs. NATURAL PRODUCT RESEARCH, 31(4), 397-403 [10.1080/14786419.2016.1169413].
Righi, G; Pelagalli, R; Isoni, V; Tirotta, I; Dallocchio, R; Dessì, A; Macchi, B; Frezza, C; Rossetti, I; Bovicelli, P
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/162631
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