5,5-disubstituted hydantoins: syntheses and anti-HIV activity.
A series of 5,5-disubstituted hydantoin derivatives was synthesized by alkylating 5,5-bis(mercaptomethyl)-2,4-imidazolidinedione (3) with various halomethylaromatic or halomethylheteroaromatic precursors, or by using the Buchener-Berg procedure on the required ketone. When evaluated for their ability to inhibit HIV-induced cell killing and virus production in CEM or MT-2 cells only compounds 2, 4n, 4o, and 4i demonstrated modest activity, the latter with an IC50 = 53 microM.
Comber
R N
RN
Organic Chemistry Department, Southern Research Institute, Birmingham, Alabama 35255-5305.
Reynolds
R C
RC
Friedrich
J D
JD
Manguikian
R A
RA
Buckheit
R W
RW
Truss
J W
JW
Shannon
W M
WM
Secrist
J A
JA
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D006678:HIV / Q000187:drug effects*; D006827:Hydantoins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests
D000998:Antiviral Agents; D006827:Hydantoins