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3-DeazanaplanocinA（3-DNPA）的新合成方法
  • ISSN号：1003-1057
  • 期刊名称：《中国药学：英文版》
  • 时间：0
  • 分类：R916.4[医药卫生—药学]
  • 作者机构：[1]北京大学医学部天然药物及仿生药物国家重点实验室,北京100191
  • 相关基金：Foundation items： National Natural Science Foundation of China （Grant No. 20472006 and 20832008）; This work was supported by the National Natural Science Foundation of China （Grant No. 20472006 and 20832008）.
作者： 李天舒[1], 陆世芳[1], 邢磊[1], 林桂椿[1], 关注[1], 杨振军[1]
关键词： 3-Deazaneplanocin, A, 3-去氮腺嘌呤, Neplanocin, A, 1-去氮嘌呤, 3-Deazaneplanocin A, 3-Deazaadenine, Neplanocin A, 1-Deazapurine
中文摘要：

3-去氮-NeplanocinA（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-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％。

英文摘要：

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,N^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.

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期刊信息
  • 《中国药学：英文版》
  • 中国科技核心期刊
  • 主管单位:中国科学技术协会
  • 主办单位:北京大学药学院
  • 主编：王夔
  • 地址：北京市学院路38号
  • 邮编：100083
  • 邮箱：zggy@mail.bjmu.edu.cn
  • 电话：010-82801713
  • 国际标准刊号：ISSN：1003-1057
  • 国内统一刊号：ISSN：11-2863/R
  • 邮发代号:
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  • 被引量:708