Organocatalytic Site-Selective Acylation of Avermectin B<sub>2a</sub>, a Unique Endectocidal Drug
نویسندگان
چکیده
منابع مشابه
Organocatalytic Site-Selective Acylation of Avermectin B2a, a Unique Endectocidal Drug.
The organocatalytic site-selective monoacylation of avermectin B2a, an insecticidal and anti-parasitic drug, was accomplished. Although an acetylation of avermectin B2a using a 4-dimethylaminopyridine (DMAP) as a catalyst gave poor site-selectivity, use of our organocatalyst increased site-selectivity of the acylation at the C-5-OH as well as the yield of monoacetate. This catalyst was also eff...
متن کاملFunctional group tolerance in organocatalytic regioselective acylation of carbohydrates.
Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functiona...
متن کاملFinal-stage site-selective acylation for the total syntheses of multifidosides A-C.
The first total syntheses of multifidosides A-C have been achieved. The synthetic strategy is characterized by catalytic site-selective acylation of unprotected glycoside precursors in the final stage of the synthesis. High functional-group tolerance of the site-selective acylation, promoted by an organocatalyst, enabled the conventionally difficult molecular transformation in a predictable and...
متن کاملAntimalarials inhibit hematin crystallization by unique drug-surface site interactions.
In malaria pathophysiology, divergent hypotheses on the inhibition of hematin crystallization posit that drugs act either by the sequestration of soluble hematin or their interaction with crystal surfaces. We use physiologically relevant, time-resolved in situ surface observations and show that quinoline antimalarials inhibit β-hematin crystal surfaces by three distinct modes of action: step pi...
متن کاملSynthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation.
A novel fluorescent photoaffinity probe of OSW-1 was prepared in two steps from a naturally occurring inactive congener by a sequential site-selective acylation strategy using Me2SnCl2. It displayed highly potent anticancer activity and a similar intracellular localization property to that of a fluorescently-tagged OSW-1, thereby demonstrating its potential utility in live cell studies.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: CHEMICAL & PHARMACEUTICAL BULLETIN
سال: 2016
ISSN: 0009-2363,1347-5223
DOI: 10.1248/cpb.c16-00205