Synthesis of some pyridoxine and pyridoxal halophosphonates

Scientific paper - Original scientific paper

• Author: Sadik Elshani
• Author: Ljubica Butula; MBZ: 6383
• Author: Julija Matijević-Sosa
• Author's institution: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of biochemistry and molecular biology)
• Scientific / art field, discipline and subdiscipline: BIOMEDICINE AND HEALTHCARE; Pharmacy; Medical Biochemistry

Abstract (english)

A new series of pyridoxine and pyridoxal chloro and fluorophosphonates have been synthesized. Partially protected pyridoxine 1, 2 or pyridoxal 4 reacted with methyl phosphonic dichloride in the presence of triethylamine at -10 °C. Thus, the following chlorophosphonate derivatives were obtained: 3,4'-0-isopropylidenepyridoxine-5'-0- methylchlorophosphonate (5), 4',5'-0-isobutylidenepyridoxine-3-0- methylchlorophosphonate (6), and monoethylacetalpyridoxal-3-0- methylchlorophosphonate (7). Similarly, from adequate starting compounds 1,3 and unprotected pyridoxal (PL) in the reaction with methyl phosphonic difluoride and triethylamine, near O"C, the corresponding 3-0 or 5'-0-methylfluorophosphonateswere obtained; 3,4'-0 isopropylidenepyridoxine-5'-0-methylfluorophosphonate(8), 4-metoxymethylpyridoxine- 5'-0-methylfluorophosphonate (9) and pyridoxal- 5'-0-methylfluorophosphonate (10).

• Language: english
• Publication type: Scientific paper - Original scientific paper
• Publication status: Published
• Peer review: Peer review - international
• Publication version: Published version
• Journal title: Croatica Chemica Acta
• Numbering: vol. 69, no. 3, pp. 1239-1249
• p-ISSN: 0011-1643
• e-ISSN: 1334-417X
• URN:NBN: urn:nbn:hr:163:608228
• Publication: 1996
• Document URL: https://hrcak.srce.hr/177142
• Type of resource: Text
• Access conditions: Open access
• Created on: 2020-04-29 14:29:56