107842-74-0Relevant articles and documents
Concise Entries to 4-Halo-2-pyridones and 3-Bromo-4-halo-2-pyridones
Honraedt, Aurélien,Gallagher, Timothy
, p. 67 - 69 (2016)
Methods for the synthesis of both simple 4-halo-2-pyridones and more functionalized 3,4-di- and (3,4,5-tri)-halo-2-pyridones are described that are based on a combination of Sandmeyer and regioselective (copper-mediated) halogenation, with a 2-chloro or a 2-benzyloxy moiety serving as a masked 2-pyridone.
Synthesis, Antitumor Activity, and Antiviral Activity of 3-Substituted 3-Deazacytidines and 3-Substituted 3-Deazauridines
McNamara, Dennis J.,Cook, P. Dan,Allen, Lois B.,Kehoe, Mary J.,Holland, Carolyn S.,Teepe, Annette G.
, p. 2006 - 2011 (2007/10/02)
Novel 3-substituted analogues of 4-amino-1-β-D-ribofuranosyl-2(1H)-pyridinone (3-deazacytidine, 3) and 4-hydroxy-1-β-D-ribofuranosyl-2(1H)-pyridinone (3-deazauridine, 4) have been synthesized and tested for antitumor and antiviral activity.Thus the 3-chloro (9a), 3-bromo (9b), and 3-nitro (9c) analogues of 3 and the 3-chloro (9d), 3-bromo (9e), and 3-nitro (9f) analogues of 4 were prepared by standard glycosylating procedures.Novel requisite heterocycles 4-amino-3-chloro-2(1H)-pyridinone (7a) and 4-amino-3-bromo-2(1H)-pyridinone (7b) were prepared by halogenating4-amino-2(1H)-pyridinone (5).Requisite heterocycles 4-amino-3-nitro-2(1H)-pyridinone (7c), 3-chloro-4-hydroxy-2(1H)-pyridinone (7d), 3-bromo-4-hydroxy-2(1H)-pyridinone (7e), and 4-hydroxy-3-nitro-2(1H)-pyridinone (7f) were synthesized by known procedures from 4-hydroxy-2(1H)-pyridinone (6).Structure proof of target nucleosides was provided by independent synthesis, 1H NMR, and UV.Compounds 9a-f were devoid of activity against intraperitoneally implanted L1210 leukemia in mice.Compound 9f displayed significant activity against rhinovirus type 34 grown in WISH cells. 4-Amino-3-fluoro-1-β-D-ribofuranosyl-2(1H)-pyridinone (1) displayed good activity against intraperitoneally implanted P388 leukemia in mice, but it was devoid of activity against M5076 sarcoma, amelanotic (LOX) melanoma xenograft, and subrenal capsule human mammary carcinoma MX-1 xenograft in mice.Compound 1 also displayed significant activity against rhinovirus type 34.
4-amino-3-halo-2-pyridinone nucleoside and nucleotide compounds
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, (2008/06/13)
4-Amino-3-halo-1-β-D-ribofuranosyl-2-(1H)-pyridinone, 4-amino-3-halo-1-(2-deoxy-β-D-pentofuranosyl)-2(1H)-pyridinone, and nucleosides and 4-amino-3-halo-1-(2-deoxy-2,2-difluoroβ-D-pentofuranosyl)-2(1H)-pyridinone nucleosides and nucleotides are useful as antiviral agents and possess in vivo activity against the L1210 murine leukemia cell line.