Hetero-expanded purine nucleosides. Design, synthesis and preliminary biological activity.
Several thieno-expanded purine nucleoside analogues were synthesized for use as tools in ongoing investigations into nucleic acid structure and function in our laboratories. The inclusion of the thiophene ring system in the nucleoside endows the purine scaffold with advantages not previously available in other reported expanded purines. The synthesis and preliminary biological studies are reported herein.
Seley-Radtke
Katherine L
KL
University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250, USA. kseley@umbc.edu
Zhang
Zhibo
Z
Wauchope
Orrette R
OR
Zimmermann
Sarah C
SC
Ivanov
Alexander
A
Korba
Brent
B
D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012324:RNA-Dependent RNA Polymerase / Q000037:antagonists & inhibitors* / Q000378:metabolism
D004791:Enzyme Inhibitors; D011684:Purine Nucleosides; D012324:RNA-Dependent RNA Polymerase
Acc Chem Res. 2002 Nov;35(11):936-43
12437318
J Am Chem Soc. 2005 Mar 16;127(10):3332-8
15755149
J Med Chem. 2000 Dec 14;43(25):4877-83
11123997
J Am Chem Soc. 1976 Jun 23;98(13):3987-94
819479
J Am Chem Soc. 2006 Nov 15;128(45):14704-11
17090058
J Am Chem Soc. 2005 Feb 9;127(5):1396-402
15686371
J Med Chem. 1990 Aug;33(8):2162-73
2165163
Acc Chem Res. 2007 Feb;40(2):141-50
17309194
J Am Chem Soc. 2000 Feb 10;122(10):2213-2222
20865137
J Org Chem. 2005 Mar 4;70(5):1612-9
15730279
Org Lett. 2003 Nov 13;5(23):4401-3
14602010
Curr Opin Chem Biol. 2007 Dec;11(6):588-94
17967435
J Org Chem. 2002 May 17;67(10):3365-73
12003548
Acc Chem Res. 2004 Oct;37(10):784-97
15491125
J Am Chem Soc. 1996 Aug 28;118(34):8182-8183
20882117
Curr Opin Chem Biol. 2003 Dec;7(6):727-33
14644182
Nucleic Acids Res. 2004 Apr 23;32(7):2241-50
15107492
Nat Struct Biol. 1998 Nov;5(11):950-4
9808038
J Am Chem Soc. 2006 Jul 19;128(28):9219-30
16834396
J Biomol Struct Dyn. 2008 Dec;26(3):283-92
18808194
Angew Chem Int Ed Engl. 2002 Oct 18;41(20):3841-4
12386865