Abstract
New amphiphilic nucleosides 3 , 5 , 7 , 9 and nucleobases 12 , 14 , with lipophilic alkynyl substituents attached to the N-heterocyclic ring were obtained in a straightforward manner by Sonogashira coupling of 5-iodouridine, 8-bromoadenosine and protected 8-bromoguanosine or related halonucleobases. In most cases protective groups were unnecessary.
Key words
nucleosides - nucleobases - cross-coupling - amphiphile - alkynes
References
1
Warner DT.
Neil GL.
Taylor AJ.
Wechter WJ.
J. Med. Chem.
1972,
15:
790
2
Shuto S.
Itoh H.
Ueda S.
Imamura S.
Fukukawa K.
Tsujino M.
Matsuda A.
Ueda T.
Chem. Pharm. Bull.
1988,
36:
209
3
Lewis LR.
Robins RK.
Cheng CC.
J. Med. Chem.
1964,
7:
200
4
Wechter WJ.
Johnson MA.
Hall CM.
Warner DT.
Berger AE.
Wenzel AH.
Gish DT.
Neil GL.
J. Med. Chem.
1975,
18:
339
5
Manfredini S.
Baralde PG.
Durini E.
Porcu L.
Angusti A.
Vertuani S.
Solaroli N.
De Clercq E.
Karlsson A.
Balzarini J.
Bioorg. Med. Chem. Lett.
2001,
11:
1329
6
Volpini R.
Costanzi S.
Lambertucci C.
Vittori S.
Klotz K.-N.
Lorenzen A.
Cristalli G.
Bioorg. Med. Chem. Lett.
2001,
11:
1931
7
Sági G.
Ötvös L.
Ikeda S.
Andrei G.
Snoeck R.
De Clercq E.
J. Med. Chem.
1994,
37:
1307
8
Lesnik EA.
Guinosso CJ.
Kawasaki AM.
Sasmor H.
Zounes M.
Cummins LL.
Ecker DJ.
Cook PD.
Freier SM.
Biochemistry
1993,
32:
7832
9
Li C.
Huang J.
Liang Y.
Langmuir
2002,
17:
2228
10
Huang J.
Ding D.
Zhang Z.
Shi B.
Liang Y.
Synth. Commun.
1997,
27:
681
11
Li C.
Huang J.
Liang Y.
Langmuir
2000,
16:
7701
12
Perez R.
Pincet F.
Goldmann M.
Mioskowski C.
Lebeau L.
Eur. Phys. J.
1998,
1
13
Bonaccio S.
Walde P.
Luisi PL.
J. Phys. Chem.
1994,
98:
6661
14
Berti D.
Keiderling U.
Baglioni P.
Progr. Colloid Polym. Sci.
2002,
120:
64
15
Pincet F.
Perez E.
Bryant G.
Lebeau L.
Mioskowski C.
Phys. Rev. Lett.
1994,
73:
2780
16
Pincet F.
Lebeau L.
Cribier SJ.
Eur. Biophys.
2001,
30:
91
17
Agrofoglio LA.
Gillaizeau I.
Saito Y.
Chem. Rev.
2003,
103:
1875
18
Loakes D.
Brown DM.
Salisbury SA.
McDougall MG.
Neagu C.
Nampalli S.
Kumar S.
Tetrahedron Lett.
2003,
44:
3387
19
McGuigan C.
Yarnold CJ.
Jones G.
Velázquez S.
Barucki H.
Brancale A.
Andrei G.
Snoeck R.
De Clercq E.
Balzarini J.
J. Med. Chem.
1999,
42:
4480
20
McGuigan C.
Barucki H.
Blewett S.
Carangio A.
Erichsen JT.
Andrei G.
Snoeck R.
De Clercq E.
Balzarini J.
J. Med. Chem.
2000,
43:
4993
21
McKeen CM.
Brown LJ.
Nicol JTG.
Mellor JM.
Brown T.
Org. Biomol. Chem.
2003,
1:
2267
22
Kahl JD.
Greenberg MM.
J. Am. Chem. Soc.
1999,
121:
598
23
McGuigan C.
Brancale A.
Andrei G.
Snoeck R.
De Clercq E.
Balzarini J.
Bioorg. Med. Chem. Lett.
2003,
13:
4511
24
Poirier D.
Boivin RP.
Berube M.
Lin S.-X.
Synth. Commun.
2003,
33:
3183
25 Hunter JH. inventors; The Upjohn Company, French Patent 1513754.
; Chem. Abstr. 1969 , 71 , 50465
26a
Sheu C.
Foote CS.
J. Am. Chem. Soc.
1995,
117:
6439
26b
Sheu C.
Kang P.
Khan S.
Foote CS.
J. Am. Chem. Soc.
2002,
124:
3905
26c
Sessler JL.
Wang R.
J. Org. Chem.
1998,
63:
4079
27
Halbfinger E.
Major DT.
Ritzmann M.
Ubl J.
Reiser G.
Boyer JL.
Harden KT.
Fischer B.
J. Med. Chem.
1999,
42:
5325
28
Liao TK.
Podrebarac EG.
Cheng CC.
J. Am. Chem. Soc.
1964,
86:
1869
29 Full details have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 228985. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.