5-Fluorouracil derivatives. I. The synthesis of 1-carbamoyl-5-fluorouracils.
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概要
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The toxicity and tumor affinity of 5-fluorouracil (<B>1</B>) have been modified by the introduction of a carbamoyl group. Carbamoylation by three general methods were studied extensively: (i) The reaction of <B>1</B> with isocyanate, (ii) the reaction of 1-chloroformyl-5-fluorouracil with amine, and (iii) the reaction of <B>1</B> with carbamoyl chloride. These three methods usually give 1 -carbamoyl-5-fluorouracils (<B>2</B>). 3-Carbamoyl-5-fluorouracils were not obtained by any method. The <B>2</B> substances take a hydrogen-bonded structure in chloroform, a non hydrogen-bonded structure in DMSO at 80 °C, and mixed structures in DMSO at 25 °C. Thirty-six homologues shown by <B>2</B> were prepared all of these compounds showed antitumor activity. Of them, 1-hexylcarbamoyl-5-fluorouracil (HCFU) appeared to be the most promising antitumor agent when administered orally in that HCFU retains well balanced lipo- and hydro-philicity, is stable in acid in the stomach, and moreover, decomposed moderately in a tumor. Isocyanate was obtained from the reaction of amine with trichloromethyl chloroformate (TCF) by simply heating these two reagents in toluene; this offers a convenient new method for synthesizing isocyanate from amine. Several new isocyanate were obtained from amino acids.
- 公益社団法人 日本化学会の論文
著者
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MORI HARUKI
Research Center, Mitsui Toatsu Chemicals
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Mizuno Haruo
Research Center, Mitsui Toatsu Chemicals, Inc.
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Ozaki Shoichiro
Research Center, Mitsui Toatsu Chemicals, Inc.
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Ishikawa Katsutoshi
Research Center, Mitsui Toatsu Chemicals, Inc.
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Ike Yoshimasa
Research Center, Mitsui Toatsu Chemicals, Inc.
関連論文
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