M. Teijeira

Synthesis and biological evaluation of 1,2-disubstituted carbonucleosides of 2-amino-6-substituted purine and 8-azapurine

One, two-disubstituted carbocyclic nucleoside analogues bearing a 2-amino-6-substituted (chloro, hydroxy or amino) purine or 8-azapurine base were prepared by constructing the base about (+/-)-2-aminocyclopentane methanol, and their activities against a selection of viruses and tumor cells were determined in vitro.

Synthesis, conformational analysis and antiviral and antitumoral activity of new 1,2-disubstituted carbocyclic nucleosides.

New 1,2-cis-disubstituted 8-azapurine-based carbocyclic analogues of nucleosides with or without a methylene between the carbocycle and the base were synthesised, starting from appropriate amino alcohols, via 6-chloro-8-azapurines; their antiviral and antitumoral activities were evaluated; and their structures were compared with that of 2,3-dideoxyadenosine (ddA) on the basis of AM1 calculations. No new compound had antiviral activity. The one with the best overall antitumoral activity against L1210, Molt4/C8 and CEM/0 cells, compound 10, was that in which the position of the hydroxymethyl group on the carbocycle relative to the heterocyclic base was closest to that found in the best-fitting low-energy conformer of ddA.

Desymmetrisation of bicyclic, meso-anhydrides by proline esters

Abstract The desymmetrisation of cyclopropane and cyclopentane derived, bicyclic meso-anhydrides using proline esters provides a versatile approach to the synthesis of enantiomerically pure amido acids which can subsequently be converted into β-amino acid containing peptide analogues.

Synthesis and biological evaluation of 1,2-disubstituted carbonucleosides of 6-substituted purine and 8-azapurine.

A series of new one two substituted carbonucleoside analogues (OTC), with the purine and 8-azapurine base linked through a methylene group at the cyclopentane ring, were synthesized and evaluated for their activity against a number of viruses and tumor cells in vitro.

SYNTHESIS AND ANTIVIRAL ACTIVITY OF 1,2-CARBONUCLEOSIDES

Abstract Members of a new class of carbonucleoside analogues (OTC, o ne t wo substituted c arbonucleosides) were synthesized and evaluated against HIV.

SYNTHESIS AND BIOLOGICAL ACTIVITY OF SOME 2-AMINOPURINE CARBONUCLEOSIDES

Abstract A series of new o ne t wo subtituted c arbonucleoside analogues (OTC) of purine was synthesized and evaluated against cytomegalovims and varicella-zoster virus in human embryonic lung (HEL) cells.

1-CYCLOPENTYLURACILS : SYNTHESIS AND CONFORMATIONAL ANALYSIS BY X-RAY CRYSTALLOGRAPHY AND AM1 THEORETICAL CALCULATIONS

Abstract A series of 1-cyclopentyl 5-substituted pyrimidines was synthesized and their energy-minimized structures were determined by AM1 and compared with the crystal structure of the parent compound, 1-cyclopentyluracil ( 2 ). As has been reported for other nucleoside analogues, the energy-minimized conformations were similar for all the compounds, but were not fully in agreement with the X-ray crystal structure obtained for 2 .

Nucleoside Analogues of Purine with a 1,2-Disubstituted Cyclopentene Ring

Abstract One, two-disubstituted carbonucleoside analogues of purine with unsaturated carbocyclic were synthesized by construction of the heterocyclic base about the primary amino group of the amino alcohol 4 intermediate, which was also synthesized in good yield starting from cyclopentadiene.

1,2-DISUBSTITUTED CARBOCYCLIC ANALOGUES OF THYMINE NUCLEOSIDES

Abstract A series of o ne t wo c arbonucleoside (OTC) analogues of thymine was synthetized and their conformation was studied by AM1 theoretical calculations. The low-energy conformations of Compound 1 and 2′,3′-dideoxythymidine, showed a degree of steric congruity.

Synthesis and structure of 5-methoxy-4-methylbenzopsoralen

Abstract5-Methoxy-4-methyl-2H-benzofuro[3,2-g]benzo-1-pyran-2-one was synthesized and its crystal structure was determined and compared with the optimal conformation arrived at by MM and AM1 theoretical calculations. The latter indicated that the tetracyclic skeleton is planar with total length (C2–C8) 9.23 å, and that the line joining the conters of the terminal-benzene and furan rings makes an angle of 30.5‡ with that joining the centers of the three rings of psoralen. The electronic properties of the reactive double bond in the pyran ring of1 are similar to those of simpler psoralens.