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2005
Nucleic acids
U 0700
Synthesis of N9- and N7-[2-Hydroxy-3-(phosphonomethoxy)propyl] Derivatives
of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds. —
12- 215 Racemic phosphonate (I) is subjected to oxirane ring opening reactions with purine
bases like (II), (V), and (IX) under standard conditions. The nucleophilic oxirane ring
opening proceeds regiospecifically yielding the corresponding N-9 substituted derivatives. Some of these derivatives undergo an intramolecular nucleophilic attack of the
2-hydroxy group on the phosphorus atom forming six-membered cyclic phosphonates,
especially adenine and diaminopurine bearing phosphonates, cf. (IV) and (VI). To obtain the free acid from cyclic phosphonate (VI), it can be treated with sodium methoxide
followed by removal of the methyl ester group in (VIII). The transformation of the N-9
alkylated products (X) into their N-6 substituted analogues (XIII) is carried out with
primary and secondary amines (XII) under exclusion of CO2. All final products are tested for cytostatic activity in vitro. No cytostatic activity is observed; the antiviral screening is under investigation. — (KRECMEROVA*, M.; MASOJIDKOVA, M.; HOLY,
A.; Collect. Czech. Chem. Commun. 69 (2004) 10, 1889-1913; Inst. Org. Chem.
Biochem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech Republic; Eng.) —
H. Hoennerscheid
2005
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