Synthesis and antiviral activities of N-mono- and/or N,N'-di-carbamoyl and acyl derivatives of symmetrical diamines.
N-carbamoyl and N-acyl diamine derivatives were synthesized from symmetrical diamines by their addition to iso(thio)cyanates, cleavage reaction of acid anhydride, or N-acylation by acyl chloride. (1R,2R)-1,2-Diaminocyclohexane [(1R,2R)-1], meso-1,2-diaminocyclohexane (meso-1), (1R,2R)-1,2-diphenylethylenediamine [(1R,2R)-3], or meso-1,2-diphenylethylenediamine (meso-3) were used as the starting symmetrical diamines. The target compounds synthesized herein were evaluated for antiviral activity with herpes simplex virus type 1 (HSV-1). A few derivatives of 1,2-diaminocyclohexane [(1R,2R)-7aa and cis-7b] with adamantyl group(s) showed significant antiviral activity (EC(50)=16.0, 27.0 microg/ml).
Mibu
Nobuko
N
Faculty of Pharmaceutical Sciences, Fukuoka University, Fukuoka, Japan.
Yokomizo
Kazumi
K
Oishi
Marumi
M
Miyata
Takeshi
T
Sumoto
Kunihiro
K
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003959:Diamines / Q000138:chemical synthesis* / Q000494:pharmacology; D018259:Herpesvirus 1, Human / Q000187:drug effects
D000998:Antiviral Agents; D003959:Diamines