嘌呤N-6-吡啶盐中间体的形成及其在嘌呤核苷合成上的应用 |
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引用本文: | 朱莉亚,林紫云,梁晓天,林太熊.嘌呤N-6-吡啶盐中间体的形成及其在嘌呤核苷合成上的应用[J].化学学报,1993,51(5):514-520. |
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作者姓名: | 朱莉亚 林紫云 梁晓天 林太熊 |
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作者单位: | 中国医学科学院药物研究所,中国医学科学院药物研究所,中国医学科学院药物研究所,耶鲁大学药理系 北京 100050,北京 100050,北京 100050,美国 |
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摘 要: | 本文报道以次黄苷为原料, 经酯化, 再在缩合剂4-氯苯磷酰二氯存在下与吡啶反应, 形成嘌呤N-6-吡啶盐中间体2, 该中间体2分别与碱性强弱不同的胺或氨及2moldm^-^3NaOH的醇溶液在室温反应, 可方便的合成6-NH2, 6-OCH3以及6-OCH2CH3-9-(β-D-呋喃核糖)嘌呤衍生物。并对以上产物形成的机制作了探讨。
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关 键 词: | 吡啶 P 胺 反应机理 吡啶 呋喃 P 腺嘌呤核苷 核糖 嘌呤 P 次黄苷 抗病毒 |
Synthesis of N-(purin-6-yl)pyridium salt and its application in synthesis of purinenucleoside |
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Abstract: | An efficient approach to convert inosine into 6-amino, 6-methoxy and 6-ethoxy derivatives that requires only mild conditions was reported. The 2',3',5'-tri-O-acetylinosine, treated with 4-ClPC6H4OPOCl2 in the presence of dry pyridine at room temperature forms fluorescent N-9-(2',3',5'-tri-O-acetyl-b-D-ribofuranosyl)purin-6yl]pyridinium chloride (I), which was treated with amines such as methylamine and piperidine in methanol at room temperature to give 6-amino-9-(b-D-2',3',5'-tri-O-acetylribofuranosyl)purine. The deacetylated adenosine was formed by using ammonia. Treatment of I with Et3N or 2 mol.dm-3 NaOH in methanol or ethanol at room temperature yielded the corresponding 6-methoxy and 6-ethoxy purine nucleoside derivative A plausible mechanism of the reaction is proposed. |
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Keywords: | PYRIDINE P AMINES REACTION MECHANISM PYRIDINE FURAN P ADENOSINE RIBOSE PURINE P |
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