Nucleosides. CXLVIII. Synthesis of 6-(β-D-ribofuranosyl)picolinamide. A novel C-nucleoside from D-ribonolactone Journal Article

  


Authors: Kabat, M. M.; Pankiewicz, K. W.; Sochacka, E.; Watanabe, K. A.
Article Title: Nucleosides. CXLVIII. Synthesis of 6-(β-D-ribofuranosyl)picolinamide. A novel C-nucleoside from D-ribonolactone
Abstract: Treatment of 2,4: 3,5-di-O-benzylidene-D-aldehydo-ribose (1) with 2-bromo-6-lithiopyridine afforded a mixture of the altro and alio isomers of 6-(2,4: 3,5-di-O-benzylidene-D-pentitol-1-yl)-2-bromopyridine (2 and 3, respectively). These isomers were chromatographically separated. Compound 2 was converted into 6-(β-D-ribofuranosyl)-2-bromopyridine (6) by mesylation of the 1’-hydroxyl group of 2 followed by treatment with trifluoroacetic acid. In a similar manner, the a-isomer 7 was prepared from 3. The same pyridine-C-nucleosides, 6 and 7, were also synthesized from the commercially available D-ribonolactone in seven steps. The bromo function of 2 and 3 was converted into the carboxamide group to give 6-(2,4: 3,5-di-O-benzyhdene-D-altro-pentitol-1-yl)picolinamide (10) and its alio isomer 11. Mesylation of 10 followed by trifluoroacetic acid treatment afforded 6-(β-D-ribofuranosyl)picolinamide (14). Similar treatment of 11 gave the a counterpart 15. © 1988, The Pharmaceutical Society of Japan. All rights reserved.
Keywords: nonhuman; biological model; cytotoxicity; chemistry; cell culture; tumor cell; lactones; ribose; nucleosides; ribonucleosides; support, u.s. gov't, p.h.s.; picolinic acids; 6-(2-bromopyridin-6-yl)-2,3-o-benzylidene-5-o-tetrahydropyranyl-d-ribofuranose; 6-(α-d-ribo-furanosyl)picolinamide; 6-(α-d-ribofuranosyl)-2-bromopyridine; 6-(β-d-ribofuranosyl)-2-bromo-pyridine; 6-(β-d-ribofuranosyl)picolinamide; d-ribonolactone; new c-nucleoside; tiazofurin analogue
Journal Title: Chemical and Pharmaceutical Bulletin
Volume: 36
Issue: 2
ISSN: 0009-2363
Publisher: Pharmaceutical Society of Japan  
Date Published: 1988-02-25
Start Page: 634
End Page: 640
Language: English
DOI: 10.1248/cpb.36.634
PUBMED: 3136937
PROVIDER: scopus
DOI/URL:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0023911334&doi=10.1248%2fcpb.36.634&partnerID=40&md5=2393538cd5ef71b107df4095684f7605
Notes: Article -- Export Date: 6 August 2020 -- Source: Scopus
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MSK Authors
  1. Kyoichi A Watanabe
    125 Watanabe
  2. Krzystof W. Pankiewicz
    43 Pankiewicz
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