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Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-beta-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4-one (2'-deoxy-9-deazaguanosine).

作者信息

Gibson E S, Lesiak K, Watanabe K A, Gudas L J, Pankiewicz K W

机构信息

Graduate School of Medical Sciences, Department of Pharmacology, Cornell University, New York, NY 10021, USA.

出版信息

Nucleosides Nucleotides. 1999 Mar;18(3):363-76. doi: 10.1080/15257779908043082.

DOI:10.1080/15257779908043082
PMID:10358941
Abstract

A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-beta-D-erythro- pentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'-deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4-one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento-furanoside (11). The anomeric configuration of the C-nucleoside was established by 1H NMR, NOEDS and ROESY. This C-nucleoside did not inhibit the growth of T-cell lymphoma cells.

摘要

相似文献

1
Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-beta-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4-one (2'-deoxy-9-deazaguanosine).
Nucleosides Nucleotides. 1999 Mar;18(3):363-76. doi: 10.1080/15257779908043082.
2
2'-Deoxy-3,7-dideazaguanosine and related compounds. Synthesis of 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl) and 1-beta-D-arabinofuranosyl-1H-pyrrolo[3,2-c]pyridin-4(5H)-one via direct glycosylation of a pyrrole precursor.2'-脱氧-3,7-二脱氮鸟苷及相关化合物。通过吡咯前体的直接糖基化反应合成6-氨基-1-(2-脱氧-β-D-赤型-戊呋喃糖基)和1-β-D-阿拉伯呋喃糖基-1H-吡咯并[3,2-c]吡啶-4(5H)-酮。
Nucleic Acids Res. 1987 Feb 11;15(3):1217-26. doi: 10.1093/nar/15.3.1217.
3
Synthesis and antitumor activity of fluorine-substituted 4-amino-2(1H)-pyridinones and their nucleosides. 3-Deazacytosines.
J Med Chem. 1987 Feb;30(2):340-7. doi: 10.1021/jm00385a016.
4
Synthesis and antiproliferative and antiviral activity of carbohydrate-modified pyrrolo[2,3-d]pyridazin-7-one nucleosides.碳水化合物修饰的吡咯并[2,3-d]哒嗪-7-酮核苷的合成及其抗增殖和抗病毒活性
J Med Chem. 1997 Feb 28;40(5):794-801. doi: 10.1021/jm960631x.
5
Synthesis and biological activity of certain 6-substituted and 2,6-disubstituted 2'-deoxytubercidins prepared via the stereospecific sodium salt glycosylation procedure.通过立体定向钠盐糖基化方法制备的某些6-取代和2,6-二取代2'-脱氧结核菌素的合成及生物活性
J Med Chem. 1985 Oct;28(10):1461-7. doi: 10.1021/jm00148a015.
6
Synthesis of pyridazine analogues of the naturally occurring nucleosides cytidine, uridine, deoxycytidine, and deoxyuridine.天然存在的核苷胞苷、尿苷、脱氧胞苷和脱氧尿苷的哒嗪类似物的合成。
J Med Chem. 1982 Jul;25(7):813-21. doi: 10.1021/jm00349a009.
7
7-Deaza-2'-deoxyguanosine.7-脱氮-2'-脱氧鸟苷
Acta Crystallogr C. 2005 Mar;61(Pt 3):o151-3. doi: 10.1107/S0108270105000971. Epub 2005 Feb 12.
8
O6-(alkyl/aralkyl)guanosine and 2'-deoxyguanosine derivatives: synthesis and ability to enhance chloroethylnitrosourea antitumor action.O6-(烷基/芳烷基)鸟苷和2'-脱氧鸟苷衍生物:合成及其增强氯乙基亚硝脲抗肿瘤作用的能力。
J Med Chem. 1997 Aug 29;40(18):2902-9. doi: 10.1021/jm960881d.
9
Nucleosides and nucleotides. 94. Radical deoxygenation of tert-alcohols in 1-(2-C-alkylpentofuranosyl) pyrimidines: synthesis of (2'S)-2'-deoxy-2'-C-methylcytidine, an antileukemic nucleoside.核苷与核苷酸。94. 1-(2-C-烷基戊呋喃糖基)嘧啶中叔醇的自由基脱氧反应:抗白血病核苷(2'S)-2'-脱氧-2'-C-甲基胞苷的合成。
J Med Chem. 1991 Jan;34(1):234-9. doi: 10.1021/jm00105a037.
10
Synthesis and antitumor evaluation in mice of certain 7-deazapurine (pyrrolo[2,3-d]pyrimidine) and 3-deazapurine (imidazo[4,5-c]pyridine) nucleosides structurally related to sulfenosine, sulfinosine, and sulfonosine.某些与亚磺腺苷、亚磺肌苷和磺基肌苷结构相关的7-脱氮嘌呤(吡咯并[2,3-d]嘧啶)和3-脱氮嘌呤(咪唑并[4,5-c]吡啶)核苷在小鼠体内的合成及抗肿瘤评价
J Med Chem. 1990 Apr;33(4):1220-5. doi: 10.1021/jm00166a021.

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