title: Anti-influenza virus activities of 2-alkoxyimino-n-(2-isoxazolin-3-ylmethyl)acetamides.
abstract: A series of 2-alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides and related compounds were synthesized and their antiviral activities against human influenza A virus were assessed. Studies of the structure-activity relationships revealed the strongest antiviral activity when position-5 of the isoxazoline ring was substituted with a tert-butyl group. When the alkoxyimino moiety was substituted with a methyl, ethyl, isopropyl or allyl group, good antiviral activity was obtained. Among the geometrical isomers at the oxime moiety, the E-isomers were more active than the Z-isomers. Among the compounds examined, (E)-2-allyloxyimino-2-cyano-N-(5-tert-butyl-2-isoxazolin-3-ylmethyl)acetamide (1j) was the most active inhibitor with an EC(50) of 3 microg/mL in vitro.
authors.affiliation: Aburahi Laboratories, Shionogi & Co., Ltd., Koka-cho, Koka-gun, 520-3423, Shiga, Japan. hiroyuki.kai@shionogi.co.jp
authors.forename: H
authors.initials: H
authors.lastname: Kai
authors.forename: H
authors.initials: H
authors.lastname: Matsumoto
authors.forename: N
authors.initials: N
authors.lastname: Hattori
authors.forename: A
authors.initials: A
authors.lastname: Takase
authors.forename: T
authors.initials: T
authors.lastname: Fujiwara
authors.forename: H
authors.initials: H
authors.lastname: Sugimoto
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D002478:Cells, Cultured / Q000187:drug effects; D006801:Humans; D009980:Influenza A virus / Q000187:drug effects*; D007555:Isoxazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D007555:Isoxazoles