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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 35, Number 3
JKCSEZ 35(3)
June 20, 1991 

Synthesis of Novel Acyclonuclosides : Study on the Synthesis and Characteristics of New N1-Substituted 5-Fluorouracil

새로운 Acyclonucloside의 합성 : 새로운 N1-Substituted 5-Fluorouracil 유도체의 합성과 그 특성에 관한 연구
Seung Ho Jung, Yong Jin Yoon, Chong Kwang Lee

정승호, 윤용진, 이종광
합성된 2-chloroethyl acrylate를 출발물질로 이용하여 5-fluorouracil의 N1-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 × 10-4/sec, 9.25 × 10-5/sec, 4.16 × 10-5/sec 이었다. 또한, 합성된 5-fluorouracil 유도체의 열분해성에 대해 논의하였다.

N1-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 N1-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 × 10-4/sec for HEFU, k = 9.25 × 10-5/sec for AOEFU, k = 4.16 × 10-5/sec for Poly(AOEFU). The differential thermal analysis and thermogravimetry of 5-fluorouracil derivatives have been discussed.

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