2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogs structurally modified by thiocarbamoylalkyl groups at the C-4 position: Synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1.
4-O-Thiocarbamoylmethyl-Neu5Ac2en 3 has strong inhibitory activity toward human parainfluenza virus type 1 (hPIV-1) sialidase compared with the parent Neu5Ac2en 2. We synthesized analogs having thiocarbamoylethyl- 4 and thiocarbamoylpropyl group 5 at the C-4 position of 2. The inhibition degrees of 4 and 5 were weaker than that of thiocarbamoylmethyl analog 3, indicating a remarkable effect of the carbon chain length in thiocarbamoylalkyl groups at the C-4 position on inhibitory activities against hPIV-1 sialidase.
Department of Organic Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan. ikeda@ys2.u-shizuoka-ken.ac.jp
Kiyoshi
K
Ikeda
Kazuki
K
Sato
Reiko
R
Nishino
Shinya
S
Aoyama
Takashi
T
Suzuki
Masayuki
M
Sato
D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D010222:Parainfluenza Virus 1, Human / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013859:Thiocarbamates
D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D013859:Thiocarbamates; C036137:2-deoxy-2,3-dehydro-N-acetylneuraminic acid; D009439:Neuraminidase; D019158:N-Acetylneuraminic Acid