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Synthesis of a Photolabeling Probe for the Study of Antiviral Mechanism of Ribavirin 被引量：1

Synthesis of a Photolabeling Probe for the Study of Antiviral Mechanism of Ribavirin
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摘要 Ribavirin has been used in urgency to treat SARS patients recently. In order to study its antiviral mechanism by photolabeling approach, we have synthesized and characterized 5-azido-1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxiamide 1 as a photolabeling probe of ribavirin. The azidotriazole nucleoside showed rapid and clean photochemical reaction, suggesting that l is a promising probe to study the antiviral mechanism of ribarivin by photolabeling. Ribavirin has been used in urgency to treat SARS patients recently. In order to study its antiviral mechanism by photolabeling approach, we have synthesized and characterized 5-azido-1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxiamide 1 as a photolabeling probe of ribavirin. The azidotriazole nucleoside showed rapid and clean photochemical reaction, suggesting that l is a promising probe to study the antiviral mechanism of ribarivin by photolabeling.
作者 QiongYouwu XunZHU JinQiaoWAN FanQiQU LingPENG
机构地区 CollegeofChemistryandMolecularSciences DepartmentofMaterialScienceandEngineering AFMBCNRSUMR
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第8期907-910,共4页 中国化学快报（英文版）
关键词 RIBAVIRIN photolabeling probe of ribavirin azidotriazole nucleoside azole nucleosides photolabeling. Ribavirin, photolabeling probe of ribavirin, azidotriazole nucleoside, azole nucleosides, photolabeling.
分类号 R978.7 [医药卫生—药品]
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参考文献11

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  • 10[10]Analytical data for compounds 1-5 :1: 1H-NMR δ ppm (DMSO-d6, 300 MHz), 7.84 (s, br, 1H), 7.68 (s, br, 1H), 5.53 (d, 1H, J=5.4 Hz), 5.45 (d, 1H, J=4.2 Hz), 5.20 (d, 1H, J=5.7 Hz), 4.76 (t, 1H, J=5.7 Hz), 4.40 (dd, 1H, J=4.8,9.9 Hz), 4.14 (dd, 1H, J=4.9, 9.9 Hz), 3.87 (dd, 1H, J=4.8, 9.9 Hz), 3.50-3.55 (m, 1H), 3.34-3.48 (m, 1H). 13C-NMR δ ppm (DMSO-d6, 75 MHz), 159.8, 155.1, 150.1, 89.5, 86.6, 74.3, 71.3, 62.9. FAB-MS m/z 308 (M+Na+), 282(M-N2+2H+Na+). IR (KBr, cm-1) 3453, 3398, 2938, 2171, 1692, 1606, 1518, 1474, 1291, 1087, 1052. UV (MeOH) λmax = 234 nm, ε = 10141 M-1cm-1.2: 1H-NMR δ ppm (CDCl3, 300 MHz), 6.09(d, 1H, J=3.0 Hz), 5.82-5.85 (m, 1H), 5.64-5.68 (m, 1H), 4.44-4.48(m, 2H), 4.12-4.18(m, 1H), 3.97(s, 3H), 2.13 (3s, 9H). 13C-NMR δ ppm (CDCl3, 75 MHz), 170.5, 169.4, 169.2, 158.8, 155.6, 131.8, 89.1, 81.8, 74.4, 71.2, 63.1, 53.4, 21.2, 21.1, 21.0. FAB-MS m/z 467(MH++2), 465 (MH+), 259. IR (CH2Cl2, cm-1) 3584, 2957, 2924, 1757, 1454, 1374, 1224, 1075. UV (EtOH), λmax = 210 nm, ε = 7160 M-1cm-1.3: 1H-NMR δ ppm (CDCl3, 300 MHz), 6.89 (d, 1H, J=2.4 Hz),5.80 (dd, 1H, J=2.4, 5.4 Hz), 5.66-5.70 (m, 1H), 4.42-4.47 (m, 2H), 4.12-4.18 (m, 1H), 4.01 (s, 3H), 2.15 (s, 3H), 2.13 (s, 3H), 2.09 (s, 3H). 13C-NMR δ ppm (CDCl3, 75 MHz), 170.0, 169.0, 168.9, 156.5, 145.8, 140.2, 89.7, 81.2, 74.7, 71.1, 63.1, 54.3, 21.7, 21.4. FAB-MS m/z 466 (M++2), 464(M+), 259, IR (CH2Cl2, cm-1 ) 3584, 2959, 2924, 1747, 1494, 1441, 1372, 1224, 1079. UV (MeOH) λmax = 240 nm, ε = 3398 M-1cm-1.4: 1H-NMR δ ppm (CDCl3, 300 MHz), 5.84(d, 1H, J=3.6 Hz), 5.74-5.77(m, 1H), 5.61-5.64(m, 1H), 4.37-4.50(m, 2H), 4.14(dd, 1H, J=4.5, 12 Hz), 3.98(s, 3H), 2.14(2s, 6H), 2.12(s, 3H). 13C-NMR δ ppm (CDCl3, 75 MHz), 170.6, 169.5, 169.3, 159.4, 153.1, 151.4, 87.3, 81.2, 73.8, 71.1, 63.1, 53.2, 21.0, 20.9, 20.8. FAB-MS m/z 427(MH+), 259, 139. IR (KBr, cm-1) 3423, 2957, 2161, 1746, 1645, 1522, 1455, 1371, 1217, 1049. UV (EtOH), λmax = 238 nm, ε = 11150 M-1cm-1.5: 1H-NMR δ ppm (DMSO-d6, 300 MHz), 8.43(s, br, 1H), 8.16(s, br, 1H), 6.68(d, 1H, J=3.6 Hz), 5.49(d, 1H, J=5.1 Hz), 5.17(d, 1H, J=5.1 Hz), 4.75(t, 1H, J=5.1 Hz), 4.35-4.36(m, 1H), 4.14-4.16(m, 1H), 3.87-3.88(m, 1H), 3.52-3.55(m, 1H), 3.40-3.44(m, 1H). 13C-NMR δ ppm (DMSO-d6, 75 MHz), 157.5, 149.7, 138.5, 91.5, 86.3, 75.1, 71.5, 63.0.

同被引文献7

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Chinese Chemical Letters
2004年 第8期

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