Premium
Design and synthesis of the 3′‐aminocarbonylamino, aminothiocarbonylamino and N ‐(Hydroxy)guanidinyl derivatives of thymidine as potential anti‐HIV agents
Author(s) -
Morin Kevin W.,
Kumar Rakesh,
Knaus Edward E.,
Wiebe Leonard I.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280346
Subject(s) - chemistry , thiourea , cyanamide , urea , ammonium hydroxide , hydroxylamine , ammonium thiocyanate , hydrolysis , thio , medicinal chemistry , derivative (finance) , methanol , chloramine t , hydrogen peroxide , organic chemistry , financial economics , economics
The 3′‐substituted‐3′‐deoxythymidines 3a (urea), 3b (thiourea) and 3c [ N ‐(hydroxy)guanidinyl)] were designed based on the known structure‐activity correlations for the active anti‐HIV agent, 3′‐azido‐3′‐deoxythymidine (AZT). Hydrolysis of 3′‐cyanamido‐3′‐deoxythymidine ( 2 ) with ammonium hydroxide in the presence of hydrogen peroxide afforded the 3′‐urea analogue 3a , whereas reaction with hydrogen sulfide in methanol gave the 3′‐thiourea derivative 3b. The 3′‐[ N ‐(hydroxy)guanidinyl] compound 3c was synthesized by reaction of the 3′‐cyanamide 2 with hydroxylamine.