2 0 0 0 OA 5-Fluorouracil Derivatives. X. : Synthesis and Antitumor Activities of α-Alkoxyalkyl-5-fluorouracils
- 著者
- 尾崎 庄一郎 渡辺 裕 / 長瀬 敏雄 小笠原 富夫 古川 弘幸 上村 敦彦 石川 勝敏 / / 徳善 令子 AKIO HOSHI MASAAKI IIGO REIKO TOKUZEN
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.34, no.1, pp.150-157, 1986-01-25 (Released:2008-03-31)
- 参考文献数
- 14
- 被引用文献数
- 15 23
With the aim of diminishing the toxicity of 5-fluorouracil (1) and obtaining biologically active derivatives of 1 suitable for oral administration, α-alkoxyalkyl groups were introduced at the 1-, 3-and 1, 3-positions of 1. Alkoxyalkylation can be effected by four methods : (i) reaction of 1-alkoxyalkyl chloride (2) with 1, (ii) reaction of acetal with 2, 4-bis (trimethylsiloxy)-5-fluoropy-rimidine, (iii) addition reaction of α-unsaturated ether with 1, (iv) aminolysis of 1-alkylthio-carbonyl-3-(1-alkoxyalkyl)-5-fluorouracil. The toxicity of the products was less than that of 1, and some of these compounds showed moderate antitumor activity against L-1210 leukemia.
1 0 0 0 OA 5-Fluorouracil Derivatives. IV. Synthesis of Antitumor-Active Acyloxyalkyl-5-fluorouracils
- 著者
- 尾崎 庄一郎 渡辺 裕 星子 知範 水野 晴雄 石川 勝敏 森 春樹
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.32, no.2, pp.733-738, 1984-02-25 (Released:2008-03-31)
- 参考文献数
- 16
- 被引用文献数
- 20 24
The toxicity and tumor affinity of 5-fluorouracil (1) have been modified by the introduction of acyloxyalkyl group (s) at the 1-, 3- or 1, 3-position (s) of 1. 1-Acyloxyalkyl-5-fluorouracil (3), 3-acyloxyalkyl-5-fluorouracil (4) and 1, 3-bis (acyloxyalkyl)-5-fluorouracil (5) were obtained by three methods : i) the reaction of α-chloroalkyl carboxylate (2) with 1, ii) the reaction of alkylidene diacylate with 2, 4-bis (trimethylsilyloxy)-5-fluoropyrimidine, iii) partial hydrolysis of 5. Compounds 3, 4 and 5 showed antitumor activity.