2beta,3beta-Difluorosialic acid derivatives structurally modified at the C-4 position: synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1.
A series of 4-O-substituted 2beta,3beta-difluorosialic acid derivatives (3a-d) has been synthesized. A key intermediate was synthesized efficiently by the electrophilic syn-addition of fluorine to the double bond of a glycal precursor using molecular fluorine or xenon difluoride in the presence of BF(3).OEt(2). Among compounds 3a-d, the 4-O-thiocarbamoylmethyl derivative 3c showed the most potent inhibitory activity against sialidase of human parainfluenza virus type 1. [structure: see text].
Ikeda
Kiyoshi
K
Department of Organic Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan. ikeda@ys2.u-shizuoka-ken.ac.jp
Kitani
Satoru
S
Sato
Kazuki
K
Suzuki
Takashi
T
Hosokawa
Chika
C
Suzuki
Yasuo
Y
Tanaka
Kiyoshi
K
Sato
Masayuki
M
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D010222:Parainfluenza Virus 1, Human / Q000187:drug effects / Q000201:enzymology*; D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000998:Antiviral Agents; D012794:Sialic Acids; D009439:Neuraminidase