Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Studied on the Synthesis of the 2-Desamino and 2-Desamino-2-Methyl Analogues of Aminopterin intermediate at Pteridine-$C_7$ Side Chain

Pteridine-$C_7$ Side Chain에서 2-탈아미노화와 2-Methyl기 치환에 따른 Aminopterin 중간체 합성에 관한 연구

  • 유의경 (세종대학교 자연과학대학 화학과) ;
  • 류성렬 (세종대학교 자연과학대학 화학과)
  • Published : 1993.01.20
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Abstract

A new series of 2-desamino, 2-desamino-2-methyl, and 2-amino analogues of aminopterin intermediates (7a), (7b), and (7c) were synthesized from 2-amino-3-cyano-6-chloromethylpyrazine. These derivatives were synthesized via two step sequence. Thus, cyclization of 2-amino-3-cyano-6-[(S-p-carbenzyloxyphenyl)thiomethyl]-pyrazine(14) with formamidine HCl, acetamidine HCl or guanidine HCl provided condensed compounds (15a), (15b) which upon base hydrolysis yielded the desired products (7a), (7b) and (7c).

2-Amino-3-cyano-6-chloromethylpyrazine으로부터 합성한 methotrexate(MTX) 중간 유도체의 모핵인 pteridine ring의 $C_2$-amino 대신 $HCH_3$기, 또는 $nH_2$기로 치환된 화합물 (7a),(7b)와 (7c)를 두 단계에 걸쳐 합성하였다. 출발물질인 dibenzyl 4,4'-dithiobisbenzoate(12)와 2-amino-3-cyano-6-chloromethylpyrazine으로부터 합성한 2-amino-3-cyano-6-[(S-p-carbenzyloxyphenyl)thiomethyl]-pyrazine(14)화합물을 formamidine HCl, acetamidine HCl과 guanidine HCl 등과 각각 반응시켜 cyclization시키고, 이 화합물을 ethanol 용매하에서 0.2N NaOH를 사용한 알칼리 가수분해로 pteroic acid유도체를 합성하였다.

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References

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