A new strategy for the synthesis of 3-deazaneplanocin A

doi:10.5246/jcps.2010.06.058

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A new strategy for the synthesis of 3-deazaneplanocin A

Tian-Shu Li, Shi-Fang Lu, Lei Xing, Gui-Chun Lin, Zhu Guan, Zhen-Jun Yang^*

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2010-06-02 Revised:2010-10-15 Online:2010-11-30 Published:2010-11-30
Contact: Zhen-Jun Yang*

Abstract

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 N⁶,N⁶,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.

Key words: 3-Deazaneplanocin A, 3-Deazaadenine, Neplanocin A, 1-Deazapurine

CLC Number:

R916.4

Supporting:

Tian-Shu Li, Shi-Fang Lu, Lei Xing, Gui-Chun Lin, Zhu Guan, Zhen-Jun Yang^* . A new strategy for the synthesis of 3-deazaneplanocin A [J]. , DOI: 10.5246/jcps.2010.06.058.

A new strategy for the synthesis of 3-deazaneplanocin A

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