Biomaterial Database

Stereochemically controlled transformations related to pyrimidine nucleosides and their analogues. 1987

V Skarić, and J Matulić-Adamić, and M Jokić

Laboratory of Stereochemistry and Natural Products, 'Ruder Bosković' Institute, Zagreb, Yugoslavia.

The diastereoisomeric differentiations and anomerizations of 5,6-dihydrothymidine and its anhydro derivatives were studied. In particular, the oxetane ring opening of (5S)-1-(3,5-anhydro-2-deoxy-beta-D-threopentofuranosyl)-5,6-dihydr othymine under acid catalysed conditions substantiated a number of the configurational modifications at the sugar moiety. The 1,3-dipolar cycloaddition to the pyrimidine C(5), C(6)-double bond was intramolecularly facilitated by the activation of 1-(3-azido-2-hydroxypropyl)uracil. (E)- and (Z)-1-Prop-enyl- and properly functionalized 1-propyl-uracil derivatives were also prepared and used for the synthesis of the tetrahydro-oxazolo[3,2-c]pyrimidine-5,6-(4H, 6H)dione and 9,3'-cyclo-3-propyl (or prop-1-enyl)-8-azaxanthine derivatives.

UI	MeSH Term	Description	Entries
D007202	Indicators and Reagents	Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)	Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D011741	Pyrimidine Nucleosides	Pyrimidines with a RIBOSE attached that can be phosphorylated to PYRIMIDINE NUCLEOTIDES.	Nucleosides, Pyrimidine
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships