著者

吉村 祐一 / 上田 享 松田 彰 Akira MATSUDA

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.40, no.7, pp.1761-1769, 1992-07-25 (Released:2008-03-31)

参考文献数

49

被引用文献数

20 28

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6, 1'-Propanouridine (10), a carbon-bridged cyclouridine fixed in the syn-conformation, was synthesized from D-fructose. Two additional carbon-units were introduced at the 1'-position of 1'-hydroxymethyl-O2, 2'-anhydrouridine 13 and inversion of the 2' hydroxyl group was achieved by sequential oxidation-reduction reactions. Finally, the spiro-carbon bridge was constructed by radical cyclization of the 1'-iodopropyl derivative of 5-chlorouridine. Dehydrochlorination followed by deprotection gave the desired 10. The circular dichroism (CD) spectrum of 10 showed a negative Cotton effect ([θ]=-6100) at the main absorption region, whereas 5'-O-tert-butyldimethylsilyl-2', 3'-O-isopropylidene-6, 1'-propanouridine (30) showed almost no Cotton band at the same absorption region. These results suggest that the critical region in which the CD Cotton effect changes from negative to positive is present in the syn region where 10 is located. Correlation of the magnitude and the direction of the sign of the CD Cotton effect and the torsion angle (χ) is also discussed.

著者

福川 清史 周東 智 平野 孝夫 上田 享

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.4, pp.1644-1646, 1984-04-25 (Released:2008-03-31)

参考文献数

7

被引用文献数

4 10

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A novel synthesis of bredinin by the conversion of AICA-riboside through a photo-degradation product is described.

著者

上田 享 碓井 博幸 周東 智 井上 英夫

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.9, pp.3410-3416, 1984-09-25 (Released:2008-03-31)

参考文献数

22

被引用文献数

18 24

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6, 5'-Cyclo-5'-deoxyuridine, a fixed anti form of uridine, was synthesized by a radical cyclization of 5'-bromo (or iodo)-5'-deoxy-2', 3'-O-isopropylidene-5-chloro (or bromo)-uridine with tri-■-butyltin hydride followed by dehydrohalogenation and deacetonation. The 5-bromo and 4-thio derivatives of the cyclouridine were also prepared and were converted to the 2', 3'-cyclic phosphates. These nucleotides were hydrolyzed by pancreatic ribonuclease. The result showed that the enzyme recognizes the pyrimidine nucleotides in the anti form. 6, 5'-Cyclo-5'-deoxycytidine was also synthesized by two routes.