Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure.
The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)-N-(pivaloyloxymethyl)benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the nitro group with sodium dithionite in aqueous solution or the palladium-catalysed transfer hydrogenation. The azanucleosides were evaluated for, but found to be devoid of, activity against several RNA- and DNA-viruses in vitro.
Gawin
Rafał
R
Faculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warszawa, Poland.
De Clercq
Erik
E
Naesens
Lieve
L
Koszytkowska-Stawińska
Mariola
M
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001372:Aza Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D002384:Catalysis; D002460:Cell Line; D004267:DNA Viruses / Q000187:drug effects*; D024882:Drug Resistance, Viral; D006801:Humans; D006865:Hydrogenation; D009705:Nucleosides / Q000138:chemical synthesis / Q000494:pharmacology*; D010165:Palladium / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000737:chemistry; D012328:RNA Viruses / Q000187:drug effects*; D013329:Structure-Activity Relationship; D000077145:Sulfanilamide; D013424:Sulfanilamides / Q000737:chemistry
D000998:Antiviral Agents; D001372:Aza Compounds; D009705:Nucleosides; D011741:Pyrimidine Nucleosides; D013424:Sulfanilamides; D000077145:Sulfanilamide; D010165:Palladium
Nucleosides Nucleotides Nucleic Acids. 2007;26(1):51-64
17162587
Med Res Rev. 1981 Summer;1(2):189-214
7050564
Antiviral Res. 1982 Dec;2(6):319-30
6299187
J Clin Virol. 2004 Jun;30(2):115-33
15125867
Antimicrob Agents Chemother. 2003 Jan;47(1):378-82
12499218
Biochemistry. 1972 Feb 1;11(3):405-13
5059120
J Infect Dis. 1980 May;141(5):563-74
6246180
Blood. 2004 Feb 1;103(3):784-9
14551141
Org Lett. 2003 Aug 7;5(16):2861-4
12889893
Nucleosides Nucleotides. 1998 May;17(5):901-10
9708331
Bioorg Med Chem. 2003 Sep 1;11(18):3889-99
12927849
Antimicrob Agents Chemother. 1989 Aug;33(8):1291-7
2552906
J Biol Chem. 2001 Nov 2;276(44):40847-57
11526116
J Org Chem. 2006 Jul 21;71(15):5599-606
16839139
Mini Rev Med Chem. 2004 Feb;4(2):189-200
14965291
Antivir Chem Chemother. 1998 Jan;9(1):1-8
9875371
Curr Top Med Chem. 2003;3(13):1467-95
14529522
J Org Chem. 1967 Dec;32(12):3775-80
5622465
J Am Chem Soc. 2003 Oct 8;125(40):12125-36
14518999
J Med Chem. 1986 Jun;29(6):1052-6
2423689
Curr Med Chem. 2003 Jun;10(11):925-53
12678681
Org Lett. 2006 Oct 12;8(21):4707-10
17020283
Lancet Oncol. 2002 Jul;3(7):415-24
12142171
Curr Med Chem. 2003 Sep;10(18):1825-43
12871107
J Antimicrob Chemother. 2003 May;51(5):1079-83
12697653
J Org Chem. 1974 Oct 4;39(20):3045-7
4416032
J Org Chem. 1965 Aug;30:2735-9
14347097
J Med Chem. 1992 Jul 24;35(15):2881-90
1495019
J Med Chem. 1989 Aug;32(8):1754-7
2547068
Br J Pharmacol. 2006 Jan;147(1):1-11
16284630
Med Res Rev. 2003 Sep;23(5):535-58
12789686
Nat Rev Drug Discov. 2005 Jul;4(7):535-6
16075486