Synthesis of Some Biologically Active Halogenopurines

다국어 초록 (Multilingual 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 $POCl_3$ 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.

국문 초록 (Abstract)

Guanine (1)으로부터 생물활성이 있는 halogenopurines계 화합물을 합성하였다. Guanine을 acetic anhydride와 반응시켜서 2,9-diacetylguanine (2-1)을 합성하여 얻어진 화합물을 $POCl_3$와 반응시켜서 화합물 3a를 합성하고, 다음 단계에서 2-amino-6-halogenopurines (3b-d)를 합성하였다. 2-Halogenopurines (2-2a-d, 4-2a-d, 5a-d)을 2-amino-6-substituted purines (1, 3a, 4-1)로부터 효율적으로 합성한 후에, 새로운 화합물인 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c 및 5d를 합성하였다. 합성한 화합물의 구조를 원소분석, $^1H$ NMR, mass spectral data로 확인하였으며, 합성한 화합물에 대한 항균 활성을 시험하였다.