Chiral HPLC Separation and Absolute Configuration of Novel S-DABO Derivatives (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• Chiral HPLC Separation and Absolute Configuration of Novel S-DABO Derivatives (Articolo in rivista) (literal)

Anno

• 2009-01-01T00:00:00+01:00 (literal)

Alternative label

• Cirilli R. Ferretti R. La Torre F. Borioni A. Fares V. Camalli M. Faggi C. Rotili D. Mai A. (2009)
  Chiral HPLC Separation and Absolute Configuration of Novel S-DABO Derivatives
  in Chirality (N.Y., N.Y. Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Cirilli R. Ferretti R. La Torre F. Borioni A. Fares V. Camalli M. Faggi C. Rotili D. Mai A. (literal)

Pagina inizio

• 604 (literal)

Pagina fine

• 612 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#altreInformazioni

• HPLC • chiral stationary phase • Chiralpak IA • absolute configuration • chiroptical properties • antiviral agents • pyrimidinone derivatives • S-DABO derivatives (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 21 (literal)

Rivista

• Chirality (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Cirilli R., Ferretti R., La Torre F., Borioni A. - ISS, Roma Fares V., Camalli M. - IC-CNR Faggi C. - Università di Firenze Rotili D., Mai A. - Università di Roma (literal)

Titolo

• Chiral HPLC Separation and Absolute Configuration of Novel S-DABO Derivatives (literal)

Abstract

• Chiral 2-(sec-butylthio)-6-[1-(2,6-dichlorophenyl)propyl]-5-methylpyrimidin-4(3H)-one (compound 1) was synthesized to serve as a model compound for structural elucidation of novel S-DABO (dihydroalkoxybenzyloxopyrimidine) derivatives endowed with potential HIV-1 reverse transcriptase inhibitory activity. Stereochemical characterization of four stereoisomers of 1 was achieved by an experimental approach based on the following steps: (a) direct HPLC enantio- and diastereoseparation at semipreparative scale; (b) determination of elution order of stereomeric mixture by using chiroptical detection (polarimeter or circular dichroism (CD)); (c) X-ray crystallography of two diastereoisomers isolated at semipreparative scale. The CD analysis of 1 and its two analogues (compounds 2 and 3), both having a single stereogenic center located in two different alkyl side chains of the dihydropyrimidinone structure, was carried out. The results of this study indicated a correlation between the absolute configuration at C-1 of alkyl side chain of the dihydropyrimidinone structure and the sign of the CD band at around 245 nm. (literal)

Prodotto di

• Institute of Crystallography (IC) (Istituto)
• Studi strutturali e funzionali di proteine di interesse biomedico e biotecnologico (PM.P01.023.001) (Modulo)

Autore CNR

• VINCENZO FARES (Persona)
• MERCEDES CAMALLI (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "Chiral HPLC Separation and Absolute Configuration of Novel S-DABO Derivatives" (Insieme di parole chiave)

Incoming links:

Autore CNR di

• VINCENZO FARES (Persona)
• MERCEDES CAMALLI (Unità di personale interno)

Prodotto

• Institute of Crystallography (IC) (Istituto)
• Studi strutturali e funzionali di proteine di interesse biomedico e biotecnologico (PM.P01.023.001) (Modulo)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Chirality (Rivista)

Insieme di parole chiave di

• Parole chiave di "Chiral HPLC Separation and Absolute Configuration of Novel S-DABO Derivatives" (Insieme di parole chiave)