title: Nitrosation of Phenolic Substrates under Mildly Basic Conditions: Selective Preparation of p-Quinone Monooximes and Their Antiviral Activities.
abstract: Nitrosation of 3-methoxyphenol and 1-naphthol were examined under both acidic (NaNO(2)-EtCO(2)H-H(2)O) and basic (i-AmNO(2)-K(2)CO(3)-DMF) conditions. Acidic nitrosations afforded ortho-directed products, whereas para-directed nitrosations were observed under basic conditions to yield p-quinone monooximes. The basic para-directed nitrosation was further examined using 15 phenols, two naphthols, and four phenolic heterocyclics. A one-pot operation of the basic nitrosation followed by methylation with dimethyl sulfate gave the corresponding methyl ethers in high yield. Two p-quinone monooximes derived from 3-methoxyphenol and 8-hydroxyquinoline showed a moderate activity against HSV-1, and the latter oxime was also effective against HSV-2. On the other hand, p-quinone monooximes derived from methyl salicylate, 1-naphthol, 7-hydroxy-2-methylbenzo[b]furan, and 8-hydroxycoumarin showed the comparable activity to that of DDI against HIV-1.
authors.affiliation: Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba 263, Japan.
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Ishikawa
authors.forename: Toshiko
authors.initials: T
authors.lastname: Watanabe
authors.forename: Hisashi
authors.initials: H
authors.lastname: Tanigawa
authors.forename: Tatsuru
authors.initials: T
authors.lastname: Saito
authors.forename: Ken-Ichiro
authors.initials: KI
authors.lastname: Kotake
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Ohashi
authors.forename: Hisashi
authors.initials: H
authors.lastname: Ishii