Ficusnotins are natural biarylbutanoids isolated from leaves of Ficus nota, a plant that is traditionally used as an alternative medicine in Southeast Asia. In this work, a concise synthesis of ficusnotin E was accomplished via ruthenium-catalyzed conjugate addition of 3,4-dimethoxyphenylboronic acid to a benzylvinyl ketone. Additionally, the other related natural 1,4-diarylbutanes derived from Ficus nota, namely, ficusnotin B, C, and F, were readily synthesized by subsequent chemical modifications of ficusnotin E. This procedure provides a concise and versatile route for the synthesis of ficusnotins and their biarylbutanoid analogs.
LatayadaFS, UyMM, AkiharaY, OhtaE, NehiraT, OmuraH, OhtaS. (2017) Ficusnotin A-F: Rare diarylbutanoids from the leaves of Ficus nota. Phytochemistry, 141, 98–104.
2.
RagasaCY, AlimoboyoguenAB, ShenCC. (2014) Chemical constituents of Ficus nota. Der Pharma Chemica, 6, 98–101.
3.
LatayadaFS, UyMM. (2016) Screening of the antioxidant properties of the leaf extracts of Philippine medical plants Ficusnota (Blanco) Merr., Metroxylon sagu Rottb., Mussaenda philippica A. Rich., Inocarpus fagifer, and Cinnamomum mercadoi Vidal. Bulletin of Environment, Pharmacology and Life Sciences, 5, 18–24.
4.
LatayadaFS, UyMM. (2016) Antimicrobial activities and toxicities of the leaf extracts of Ficusnota (Blanco) Merr. Asian Journal of Biological and Life Science, 5, 248–252.
5.
VietMH, ChenCY, HuCK, ChenYR, LiMS. (2013) Discovery of dihydrochalcone as potential lead for Alzheimer's disease: In silico and in vitro study. PLoS ONE, 8, e79151.
6.
QinX, XingYF, ZhouZ, YaoY. (2015) Dihydrochalcone compounds isolated from crabapple leaves showed anticancer effects on human cancer cell lines. Molecules, 20, 21193–21203.
7.
MohammedMM, HamdyAHA, El-FikyNM, MettwallyWSA, El-BeihAA, KobayashiN. (2014) Anti-influenza A virus activity of a new dihydrochalcone diglycoside isolated from the Egyptian seagrass Thalassodendron ciliatum (Forsk.) den Hartog. Natural Product Research, 28, 377–382.
8.
MiyauraN, SuzukiA. (1995) Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chemical Reviews, 95, 2457–2483.
9.
ZhangL, XieX, FuL, ZhangZ. (2013) [RuCl2(p-cymene)]2-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated ketones under ligand-free and neutral conditions. Journal of Organic Chemistry, 78, 3434–3437.
CloonanSM, KeatingJJ, ButlerSG, KnoxAJS, JørgensenAM, PetersGH, RaiD, CorriganD, LloydDG, WilliamsC, MeeganMJ. (2009) Synthesis and serontonin transporter activity of sulphur-substituted α-alkyl phenethylamines as a new class of anticancer agents. European Journal of Medicinal Chemistry, 41, 4862–4888.
12.
BlackerAJ, RoyM, HariharanS, HeadleyC, UpareA, JagtapA, WankhedeK, MishraSK, DubeD, BhiseS, VishwasraoS, KadamN. (2010) Convenientmethod for synthesis of N-protected α-amino epoxides: key intermediates for HIV protease inhibitors. Organic Process Research & Development, 15, 331–338.