Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of Novel Acyclonuclosides : Study on the Synthesis and Characteristics of New $N_1$-Substituted 5-Fluorouracil

새로운 Acyclonucloside의 합성 : 새로운 $N_1$-Substituted 5-Fluorouracil 유도체의 합성과 그 특성에 관한 연구

  • Seung Ho Jung (Department of Chemistry, Gyeongsang National University) ;
  • Yong Jin Yoon (Department of Chemistry, Gyeongsang National University) ;
  • Chong Kwang Lee (Department of Chemistry, Gyeongsang National University)
  • 정승호 (경상대학교 자연과학대학 화학과) ;
  • 윤용진 (경상대학교 자연과학대학 화학과) ;
  • 이종광 (경상대학교 자연과학대학 화학과)
  • Published : 1991.06.20
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Abstract

$N_1-alkyl-5-fluorouracil$ derivatives from 2-chloro-ethylacrylate(CEA) were synthesized. The reaction of 5-fluorouracil(5-FU) with 2-chloroethyl acrylate gave 1-hydroxyethyl-5-fluorouracil(HEFU) in 70% yield. The treatment of HEFU with acryloyl chloride afforded 1-acryloyloxyethyl-5-fluorouracil (AOEFU). Poly(1-acryloyloxyethyl-5-fluorouracil)[Poly(AOEFU)] was also synthesized from 5-fluorouracil and Poly(CEA). The hydrolysis rates of $N_1-alkyl-5-fluorouracil$ derivatives were observed by means of UV spectrophotometer at 265 nm in ethanol-water(1 : 1); k = the constant of hydrolysis rate, $k=1.38{\times}10^{-4}$/sec for HEFU, $k=9.25{\times}10^{-5}$/sec for AOEFU, $k=4.16{\times}10^{-5}$k = 4.16 ${\times}$ $10-5}sec$ for Poly(AOEFU). The differential thermal analysis and thermogravimetry of 5-fluorouracil derivatives have been discussed.

합성된 2-chloroethyl acrylate를 출발물질로 이용하여 5-fluorouracil의 $N_1$-위치에 각각 hydroxyethyl, acryloyloxyethyl, poly(acryloyloxyethyl)기를 가진 5-fluorouracil 유도체를 높은 수율로 얻었다. 이들 유도체들과 HCl과의 가수분해속도를 물-에탄올(1:1) 혼합용매에서 UV 분광기를 이용하여 측정하였다. 1-hydroxyethyl-5-fluorouracil, 1-acryloyloxyethyl-5-fluorouracil 및 Poly(1-acryloyloxyethyl-5-fluorouracil)의 가수분해속도는 각각 $k=1.38{\times}10^{-4}$sec, $9.25{\times}10^{-5}$/sec, $4.16{\times}10^{-5}$/sec 이었다. 또한, 합성된 5-fluorouracil 유도체의 열분해성에 대해 논의하였다.

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