Schistosomicidal Activity of Dihydrobenzofuran Neolignans

• Published in: Chemistry & biodiversity Vol. 15; no. 7; pp. e1800134 - n/a
• Main Authors: Dias, Herbert J., Patrocínio, Andressa B., Pagotti, Mariana C., Fukui, Murilo J., Rodrigues, Vanderlei, Magalhães, Lizandra G., Crotti, Antônio E. M.
• Format: Journal Article
• Language: English
• Published: Switzerland Wiley Subscription Services, Inc 01-07-2018
• Subjects: Acids; Animals; benzofuran neolignans; Dose-Response Relationship, Drug; Lignans - chemical synthesis; Lignans - chemistry; Lignans - pharmacology; Molecular Structure; neglected diseases; oxidative coupling; phenylpropanoids; Praziquantel; Schistosoma mansoni; Schistosoma mansoni - drug effects; Schistosomicides - chemical synthesis; Schistosomicides - chemistry; Schistosomicides - pharmacology; benzofuran neolignans; neglected diseases; Schistosoma mansoni; oxidative coupling; phenylpropanoids
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201800134

We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)‐trans‐dehydrodicoumaric acid dimethyl ester (1) and (±)‐trans‐dehydrodiferulic acid dimethyl ester (2) against adult Schistosoma mansoni worms in vitro. Compound 4 ((±)‐trans‐4‐O‐acetyldehydrodiferulic acid dimethyl ester) displayed the most promising activity; at 200 μm, it kills 100 ± 0% of worms after 24 h, which resembles the result achieved with praziquantel (positive control) at 1.56 μm. The hydrogenation of the double bond between C7′ and C8′, the introduction of an additional methyl group at C3′, and a double bond between C7 and C8 decreased the schistosomicidal activity of DBNs. On the other hand, the presence of the acetoxy group at C4 played an interesting role in this activity. These results demonstrated the interesting schistosomicidal potential of DBNs, which could be further exploited.