We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Total Synthesis of the Natural Chalcone Lophirone E, Synthetic Studies toward Benzofuran and Indole-Based Analogues, and Investigation of Anti-Leishmanial Activity.
- Authors
Pozzetti, Luca; Ibba, Roberta; Rossi, Sara; Taglialatela-Scafati, Orazio; Taramelli, Donatella; Basilico, Nicoletta; D'Alessandro, Sarah; Parapini, Silvia; Butini, Stefania; Campiani, Giuseppe; Gemma, Sandra
- Abstract
The potential of natural and synthetic chalcones as therapeutic leads against different pathological conditions has been investigated for several years, and this class of compounds emerged as a privileged chemotype due to its interesting anti-inflammatory, antimicrobial, antiviral, and anticancer properties. The objective of our study was to contribute to the investigation of this class of natural products as anti-leishmanial agents. We aimed at investigating the structure–activity relationships of the natural chalcone lophirone E, characterized by the presence of benzofuran B-ring, and analogues on anti-leishmania activity. Here we describe an effective synthetic strategy for the preparation of the natural chalcone lophirone E and its application to the synthesis of a small set of chalcones bearing different substitution patterns at both the A and heterocyclic B rings. The resulting compounds were investigated for their activity against Leishmania infantum promastigotes disclosing derivatives 1 and 28a,b as those endowed with the most interesting activities (IC50 = 15.3, 27.2, 15.9 μM, respectively). The synthetic approaches here described and the early SAR investigations highlighted the potential of this class of compounds as antiparasitic hits, making this study worthy of further investigation.
- Subjects
BENZOFURAN; CHALCONE; STRUCTURE-activity relationships; CHALCONES; LEISHMANIA infantum; NATURAL products
- Publication
Molecules, 2022, Vol 27, Issue 2, p463
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27020463