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ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 54, Number 4
JKCSEZ 54(4)
August 20, 2010 |
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Title |
Synthesis of Some Biologically Active Halogenopurines
생물 활성이 있는 Halogenopurines의 합성
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Author |
Yu Lin Hu, Xiang Liu, Ming Lu*, Qiang Ge, Xiao Bin Liu
Yu Lin Hu, Xiang Liu, Ming Lu*, Qiang Ge, Xiao Bin Liu |
Keywords |
Halogenopurines, 2-Amino-6-chloropurine, Phase transfer catalyst, Chlorine-exchange halogenation, Diazotization, Fungicidal activity
, Halogenopurines, 2-Amino-6-chloropurine, Phase transfer catalyst, Chlorine-exchange halogenation, Diazotization, Fungi |
Abstract |
A series of some biologically active halogenopurines were synthesized from commercially available guanine (1). The reaction of guanine with acetic anhydride yielded 2,9-diacetylguanine (2-1) by acetylation reaction. Further treatment of 2-1 with POCl3 by PEG-2000 phase transfer catalysis furnished the important compound 3a, then 2-amino-6-halogenopurines (3b-d) were obtained through chlorine-exchange halogenations between KX and 3a by TPPB phase transfer catalyst. Further, 2-halogenopurines (2-2a-d, 4-2a-d, 5a-d) were efficiently prepared from 2-amino-6-substituted purines (1, 3a, 4-1) via a diazotization catalyzed by their corresponding CuX, and some new compounds 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c and 5d have been discovered. The structures of synthesized compounds were mainly established on the basis of their elemental analysis, 1H NMR, as well as their mass spectral data. All the title compounds were screened for their antifungal activities, and some of the compounds showed promising activity.
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429 - 436 |
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