Synthesis, separation and anti-HIV activity of distereoisomers of N-[p-(4-bromophenyl) -2',3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester (stampidine).
The distereoisomers of stampidine (STAMP, DDE-113, HI-113, N-[p-(4-bromophenyl)-2'3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester, CAS 217178-62-6) were separated using two different procedures. The first method involved separation of the isomers by fractional crystallization, and the second method utilized a preparative HPLC. Both isomers were active against the HIV-1 strain HTLV(IIIB) and neither isomer was more or less active than distereoisomeric mixture of stampidine.
Venkatachalam
Taracad K
TK
Parker Hughes Institute, Roseville, Minnesota, USA.
Qazi
Sanjive
S
Uckun
Fatih M
FM
D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003460:Crystallization; D054306:Dideoxynucleotides; D006678:HIV / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D009000:Monocytes / Q000821:virology; D018119:Stavudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013938:Thymidine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D019380:Anti-HIV Agents; D054306:Dideoxynucleotides; C472384:stampidine; D013938:Thymidine Monophosphate; D018119:Stavudine