Synthesis of 6-acetamido-5-amino- and -5-guanidino-3, 4-dehydro-N-(2-ethylbutyryl)- 3-piperidinecarboxylic acids related to zanamivir and oseltamivir, inhibitors of influenza virus neuraminidases.
[reaction: see text] 6-Acetamido-5-amino- and -5-guanidino-3, 4-dehydro-N-(2-ethylbutyryl)-3-piperidinecarboxylic acids (8 and 9) have been synthesized starting from natural siastatin B, a bacterial neuraminidase inhibitor isolated from Streptomyces culture in a stereospecific fashion. These compounds are related to zanamivir and oseltamivir, inhibitors of influenza virus neuraminidases.
Shitara
E
E
Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
Nishimura
Y
Y
Nerome
K
K
Hiramoto
Y
Y
Takeuchi
T
T
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003016:Clostridium perfringens / Q000201:enzymology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006146:Guanidines; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000201:enzymology*; D053139:Oseltamivir; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011714:Pyrans; D012794:Sialic Acids / Q000737:chemistry*; D053243:Zanamivir
D000081:Acetamides; D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D006146:Guanidines; D010880:Piperidines; D011714:Pyrans; D012794:Sialic Acids; D053139:Oseltamivir; C011353:siastatin; D009439:Neuraminidase; D053243:Zanamivir