152433-65-3Relevant academic research and scientific papers
Synthesis of certain 6-(arylthio)uracils as potential antiviral agents
El-Emam, Ali A.,Nasr, Magda N. A.,Pedersen, Erik B.,Fouad, Tarek,Nielsen, Claus
, p. 25 - 35 (2001)
A series of 6-(Arylthio)uracils have been prepared via condensation of 6-chlorouracil or 5-ethyl-6-chlorouracil with the corresponding thiopnenol derivatives in pyridine or ethanolic potassium hydroxide. The synthesized compounds were tested for their antiviral activity. Some of the 5-ethyl-6-(arylthio)uracil derivatives 10a-g showed moderate activities against hepatitis B Virus (HBV) and HIV-1 virus.
A simple and convenient synthesis of HEPT analogues via a one-pot reduction - Sulfenylation reaction
Sun, Guangfu,Kuang, Yunyan,Wang, Suxi,Chen, Fener
, p. 2229 - 2235 (2007/10/03)
The one-pot reduction - sulfenylation of 5-alkyl-6-chlorouracils (1) with diaryl disulfides (2) and sodium borohydride in methanol was carried out to afford 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine HEPT analogues in good to excellent yields.
Antiviral 2, 4-pyrimidinedione derivatives
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, (2008/06/13)
Novel 2,4-pyrimidinedione compounds, and pharmaceutically acceptable salts thereof which possess good antiviral activities, and specifically represented by the following formula(I): STR1 wherein: R 1 represents an unsubstituted or substituted allyl group represented by CH 2 CH CR 5 R 6 or an unsubstituted or substituted propargyl group represented by CH 2 C CR 7 wherein R 5, R 6 and R 7 are each independently a hydrogen atom; a methyl group optionally substituted with a halogen atom, or a C 1-10 carbonyloxy, hydroxy, azido, cyano, optionally substituted amino, optionally substituted phosphonyl, optionally substituted phenyl, C 3-10 heteroaryl, C 1-3 alkoxy or benzyloxy radical; a C 2-10 alkyl or alkenyl group; a cyclopropyl group; an optionally substituted phenyl group; a C 3-10 heteroaryl group; a C 1-10 ester group; or an optionally substituted C 1-10 alkylamide group;R 2 represents a halogen atom, an optionally substituted C 1-5 alkyl, C 3-6 cycloalkyl, C 2-8 alkenyl, C 2-8 alkynyl group or a benzyl group;R 3 and R 4 represent independently a hydrogen or halogen atom, or a hydroxy, C 1-3 alkyl, fluoromethyl, C 1-3 alkoxy, amino, C 2-6 alkylester or C 2-7 alkylamide group;A represents an oxygen or sulfur atom;Z represents an oxygen or sulfur atom; a carbonyl group; an amino group; or a methylene group optionally substituted with at least one selected from the group consisting of a halogen atom, and a cyano, hydroxy, azido, amino, C 1-3 alkylamide, C 1-4 ester, and nitro groups.
Synthesis and anti-HIV activity of novel N-1 side chain-modified analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)
Pontikis, Renée,Benhida, Rachid,Aubertin, Anne-Marie,Grierson, David S.,Monneret, Claude
, p. 1845 - 1854 (2007/10/03)
A series of 33 N-1 side chain-modified analogs of 1-[(2- hydroxyethoxy)methyl]-6-(phenylthio)thymine (1, HEPT) were synthesized and evaluated for their anti-HIV-1 activity. In particular, the influence of substitution of the terminal hydroxy group of the acyclic structure of HEPT and the structural rigidity of this side chain were investigated. Halo (7, 8), azido (9), and amino (10-15) derivatives were synthesized from HEPT via the p-tosylate derivative 6. Acylation of the primary amine 15 afforded the amido analogs 16-20. The diaryl derivatives 26-29 were prepared by reaction of HEPT, or of the 6-(2-pyridylthio) analog 23, with diaryl disulfides in the presence of tri-n-butylphosphine. Compounds 39-41, in which the N-1 side chain is rigidified by incorporation of an E-configured double bond, were obtained by palladium(0)-catalyzed coupling of several different 6- (arylthio)uracil derivatives (37, 38) with allyl acetates 33. Compounds 13, 40a,c,d,f, and 41, incorporating an aromatic ring at the end of the acyclic side chain, were found to be more potent than the known diphenyl-substituted HEPT analog BPT (2), two of them, 40c,d, being 10-fold more active.
