Synthesis and antiviral activities of some 4,4'- and 2,2'-dihydroxytriphenylmethanes.
We synthesized some 4,4'- and 2,2'-dihydroxytriphenylmethane derivatives 3a--e and 4a--c by condensation of phenol 1 and aromatic aldehyde 2 in moderate to good yields (30--83%). Most of them showed significant antiviral activity against herpes simplex virus type 1 (anti-HSV-1 activity) in a plaque reduction assay. The most potent antiviral activity (EC(50)=0.79 microg/ml) was observed in the 4,4'-dihydroxytriphenylmethane derivative 3b. This compound 3b showed lower cytotoxicity (CC(50)=30.2 microg/ml), compared to that of the prototype 3a.
Mibu
Nobuko
N
Faculty of Pharmaceutical Sciences, Fukuoka University; 8-19-1 Nanakuma, Jonan-ku, Fukuoka 862-0973, Japan.
Yokomizo
Kazumi
K
Uyeda
Masaru
M
Sumoto
Kunihiro
K
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002522:Chlorocebus aethiops; D018259:Herpesvirus 1, Human / Q000187:drug effects; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D014709:Vero Cells; D010948:Viral Plaque Assay
D000447:Aldehydes; D000998:Antiviral Agents; D010636:Phenols; D008697:Methane