3-nitropyrrole nucleoside

• US 5,438,131 A
• Filed: 09/16/1992
• Issued: 08/01/1995
• Est. Priority Date: 09/16/1992
• Status: Expired due to Term

• Current Assignee: Purdue Research Foundation (The Trustees of Purdue University (d/b/a Purdue University)), Board of Regents of the University of Michigan (University of Michigan)
• Original Assignee: Board of Regents of the University of Michigan (University of Michigan)
• Inventors: Zhang, Peiming, Andrews, Philip C., Nichols, Ruthann, Bergstrom, Donald E.
• Primary Examiner(s): Robinson, Douglas W.
• Assistant Examiner(s): LANKFORD JR, LEON B
• Application Number:
  US07/946,971
• Time in Patent Office: 1,049 Days
• Field of Search: 536/18.7, 536/22.1, 536/26.1, 536/26.9, 536/28.6, 536/28.7, 536/28.8, 536/28.9
• US Class Current: 536/28.6
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 19/044 Pyrrole radicals
• CPC Class Codes: C07H 19/052 Imidazole radicals
• CPC Class Codes: C07H 19/056 Triazole or tetrazole radicals
• CPC Class Codes: C07H 19/24 Heterocyclic radicals containing oxygen or sulfur as ring hetero atom
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

Abstract

Oligonucleotides having at least ten nucleosides, at least two of which are selected from the group consisting of A, T, C and G, and at least one nucleoside being a universal nucleoside of the formula: ##STR1## wherein: each R_n is H, OH, F or OCH₃ ;

Z is a member of the group consisting of O, S and CH₂ ; and

B is a five-membered, heterocyclic base having at least two double bonds, and further having an electron withdrawing group bonded thereto, said base with electron withdrawing group being represented by the formula: ##STR2## wherein: said base with electron withdrawing group is bonded at X₄ to the sugar portion of the nucleoside;

X₁, X₃ and X₅ are each members of the group consisting of N, O, C, S and Se;

X₂ and X₄ are each members of the group consisting of N and C; and

W is a member of the group consisting of F, Cl, Br, I, O, S, OH, SH, NH₂, NO₂, C(O)H, C(O)NHOH, C(S)NHOH, NO, C(NOCH₃)NH₂, OCH₃, SCH₃, SeCH₃, ONH₂, NHOCH₃, N₃, CN, C(O)NH₂, C(NOH)NH₂, CSNH₂ and CO₂ H.

Claims

1. A nucleoside of the formula:

##STR8##