5-할로겐 치환 uracil 들의 4-Thiosugar Nucleosides의 합성 (제 1 보)

Synthesis of 1-(4'-Thio-${\alpha},{\beta}$-D-ribofuransyl)-5-halogeno Uracils (I)

  • Kim Jack C. (Department of Chemistry, College of Liberal Arts and Sciences, Busan National University) ;
  • Lee Euk-suck (Department of Chemistry, College of Liberal Arts and Sciences, Busan National University) ;
  • Kim Chang-bae (Department of Chemistry, Dan-kook University) ;
  • Bobek Miroslav (Department of Experimental Therapeutics, Roswell Park Memorial Institute) ;
  • Whistlee Roy L. (Department of Biochemistry, Purdue University)
  • 발행 : 1975.04.30

초록

와 5-iodo-pyrimidine nucleoside 의 4'-thio 유도체들은 2,3,5-tri-O-aceytl-4-thio-D-ribofuranosyl chloride 와 5-halogeno-2,4-bis(trimethylsiloxy)pyrimidine의 chloromercury 유도체를 축합시킨후 보호작용기를 제거함으로써 합성하였다. 4'-Thio 유도체들의 생물학적 활성도는 예비시험에서는 이에 대응하는 4'-oxygen 유도체들과 큰 차이가 나지 않지만 4'-thio유도체가 비교적 더높은 활성을 가진다는 사실은 흥미로운 일이며 앞으로 생화학적인 고찰을 계속하는 것은 가치있는 일임을 보여주고 있다.

The 4'-thio analogs of the 5-bromo-and 5-iodo-pyrimidine nucleosides were prepared by condensation of 2,3,5-tri-O-acetyl-4-thio-${\alpha},{\beta}$-D-ribofuranosyl chloride with the chloromercury derivatives of 5-halogeno-2,4-bis(trimethylsiloxy)pyrimidine, followed by the removal of the protecting groups. Although the biological activities of the 4'-thio derivatives are not greatly different from the corresponding 4'-oxygen analogs in this preliminary test, the fact that the 4'-thio analogs have comparableihigh activities, is of interest, and indicates the value of further biochemical examinations.

키워드

참고문헌

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