Abstract
The synthesis and the anti-HIV-1 activity of a series of 2-arylthio-6-benzyl-2,3-dihydro-1H -pyrimidin-4-ones (aryl S -DABOs) are reported. These compounds were synthesized via a coupling reaction of
the corresponding 6-benzyl-2-thiouracils with aryl iodides in the presence of neocuproine
hydrate, copper(I) iodide, and sodium tert -butoxide. Target compounds showed moderate activity against HIV-1.
Key words
medicinal chemistry - antiviral agents - HIV - non-nucleosides -
S -DABO
References <A NAME="RZ26806SS-1">1 </A>
On leave from Chemistry Department, Faculty of Education Kafr El-Sheikh branch, Tanta
University, Kafr El-Sheikh, Egypt.
<A NAME="RZ26806SS-2">2 </A>
A research center funded by the Danish National Research Foundation for Studies on
Nucleic Acid Chemical Biology.
<A NAME="RZ26806SS-3">3 </A>
Tronchet JMJ.
Seman M.
Curr. Top. Med. Chem.
2003,
13:
1496
<A NAME="RZ26806SS-4">4 </A>
Tarby CM.
Curr. Top. Med. Chem.
2004,
4:
1045
<A NAME="RZ26806SS-5">5 </A>
Sluis-Cremer N.
Temiz NA.
Bahar I.
Curr. HIV Res.
2004,
2:
323
<A NAME="RZ26806SS-6">6 </A>
Zhang Z.
Hamatake R.
Hong Z.
Antivir. Chem. Chemother.
2004,
15:
121
<A NAME="RZ26806SS-7">7 </A>
Antinori A.
Zaccarelli M.
Cingolani A.
Forbici F.
Rizzo MG.
Trotta MP.
Di Giambenedetto S.
Narciso P.
Ammassari A.
Giradi E.
De Luca A.
Perno CF.
AIDS Res. Hum. Retroviruses
2002,
18:
835
<A NAME="RZ26806SS-8">8 </A>
Tanaka H.
Takashima H.
Ubasawa M.
Sekiya K.
Inouye N.
Baba M.
Shigeta S.
Walker RT.
De Clercq E.
Miyasaka T.
J. Med. Chem.
1995,
38:
2860
<A NAME="RZ26806SS-9">9 </A>
Baba M.
Tanaka H.
Miyasaka T.
Yuasa S.
Ubasawa M.
Walker RT.
De Clercq E.
Nucleosides Nucleotides
1995,
14:
575
<A NAME="RZ26806SS-10">10 </A>
Artico M.
Drugs Future
2002,
27:
159
<A NAME="RZ26806SS-11">11 </A>
Marongiu ME.
Pani A.
Musiu C.
La Colla P.
Mai A.
Sbardella G.
Massa S.
Artico M.
Recent Res. Dev. Med. Chem.
2001,
1:
65
<A NAME="RZ26806SS-12">12 </A>
Marongiu, M. E.; Pani, A.; Artico, M.; Massa, S.; Mai, A.; La Colla, P. Abstracts of Papers , VIII International Conference on AIDS, Amsterdam, July 19-24, 1992 ; PoA 2315.
<A NAME="RZ26806SS-13">13 </A>
Artico M.
Massa S.
Mai A.
Marongiu ME.
Piras G.
Tramontano E.
La Colla P.
Antivir. Chem. Chemother.
1993,
4:
361
<A NAME="RZ26806SS-14">14 </A>
Tramontano E.
Marongiu ME.
De Montis A.
Loi AG.
Artico M.
Massa S.
Mai A.
La Colla P.
Microbiologica
1994,
17:
269
<A NAME="RZ26806SS-15">15 </A>
Massa S.
Mai A.
Artico M.
Sbardella G.
Tramontano E.
Loi AG.
Scano P.
La Colla P.
Antivir. Chem. Chemother.
1995,
6:
1
<A NAME="RZ26806SS-16">16 </A>
Mai A.
Artico M.
Sbardella G.
Massa S.
Loi AG.
Tramontano E.
Scano P.
La Colla P.
J. Med. Chem.
1995,
38:
3258
<A NAME="RZ26806SS-17">17 </A>
Ragno R.
Mai A.
Sbardella G.
Artico M.
Massa S.
Musiu C.
Mura M.
Marturana E.
Cadeddu A.
La Colla P.
J. Med. Chem.
2004,
47:
928
<A NAME="RZ26806SS-18">18 </A>
Mai A.
Artico M.
Sbardella G.
Massa S.
Loi AG.
Tramontano E.
Scano P.
La Colla P.
J. Med. Chem.
1995,
38:
3258
<A NAME="RZ26806SS-19">19 </A>
He Y.
Chen F.
Sun G.
Wang Y.
De Clercq E.
Balzarini J.
Pannecouque C.
Bioorg. Med. Lett.
2004,
14:
3173
<A NAME="RZ26806SS-20">20 </A>
Manetti F.
Este JA.
Clotet-Codina I.
Armand-Ugon M.
Maga G.
Crespan E.
Cancio R.
Mugnaini C.
Bernardini C.
Togninelli A.
Carmi C.
Alongi M.
Petricci E.
Massa S.
Corelli F.
Botta M.
J. Med. Chem.
2005,
48:
8000
<A NAME="RZ26806SS-21">21 </A>
Mugnaini C.
Manetti F.
Esté JA.
Clotet-Codina I.
Maga G.
Cancio R.
Botta M.
Corelli F.
Bioorg. Med. Chem. Lett.
2006,
16:
3541
<A NAME="RZ26806SS-22">22 </A>
Pedersen OS.
Pedersen EB.
Synthesis
2000,
479
<A NAME="RZ26806SS-23">23 </A>
Pedersen OS.
Pedersen EB.
Antivir. Chem. Chemother.
1999,
10:
285
<A NAME="RZ26806SS-24">24 </A>
Petersen L.
Pedersen EB.
Nielsen C.
Synthesis
2001,
559
<A NAME="RZ26806SS-25">25 </A>
Petersen L.
Hansen TH.
Khalifa NM.
Jørgensen PT.
Pedersen EB.
Nielsen C.
Monatsh. Chem.
2002,
133:
1031
<A NAME="RZ26806SS-26">26 </A>
Wamberg M.
Pedersen EB.
El-Brollosy NR.
Nielsen C.
Bioorg. Med. Chem.
2004,
12:
1141
<A NAME="RZ26806SS-27">27 </A>
Therkelsen FD.
Hansen A.-L.
Pedersen EB.
Nielsen C.
Org. Biomol. Chem.
2003,
1:
2908
<A NAME="RZ26806SS-28">28 </A>
Pedersen OS.
Petersen L.
Brandt M.
Nielsen C.
Pedersen EB.
Monatsh. Chem.
1999,
130:
1499
<A NAME="RZ26806SS-29">29 </A>
Danel K.
Pedersen EB.
Nielsen C.
J. Med. Chem.
1998,
41:
191
<A NAME="RZ26806SS-30">30 </A>
He H.
Llauger L.
Rosen N.
Chiosis G.
J. Org. Chem.
2004,
69:
3230
<A NAME="RZ26806SS-31">31 </A>
Pauwels R.
Balzarini J.
Baba M.
Snoeck R.
Schols D.
Hederwijn P.
Desmyter J.
De Clercq E.
J. Virol. Methods
1988,
20:
309
<A NAME="RZ26806SS-32">32 </A>
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