【摘要】 3-去氮-Neplanocin A(3-DNPA,2)是具有很强抗病毒抗肿瘤活性的碳环核苷。发展其有效的合成路线,有助于其类似物的合成及进一步的生物活性研究。由2,4-二羟基-3-硝基吡啶起始的3-去氮嘌呤合成,采用一釜反应直接构建咪唑环,避免了中间体10被氧化;同时,碱基合成中副产物11-1的发现和结构确证,提示了一条合成1-去氮嘌呤的新方法。采用微波辅助方法提高了6-氯-3-去氮嘌呤12的肼解及随后的Boc保护制备17的反应产率;而后者提高了偶联反应N9异构体的比例。全部合成工作经十步反应得到3-DNPA,总收率11.2%。更多还原

【Abstract】 3-Deazaneplanocin A(3-DNPA,2),an antiviral and antitumor agent,has been synthesized in an optimized procedure in 10 steps,with an increased overall yield of 11.2%.Started from 2,4-dihyroxyl-3-nitropyridine,reduction of nitro group and ring closure of imidazole were carried out in one pot,without the separation of diaminopyridine(10),to give 3-deazapurine(11). Moreover,the conversion of 6-chloro-3-deazapurine(12) to 6-amino-3-deazapurine(13) and the synthesis of N~6,M~6,N9-tris-Boc-3- deazadenine(16) was promoted by microwave-aid method.Compound 16 benefited the formation of N9 isomer of 3-DNPA in Mitsunobu reaction.更多还原