Stereocontrolled Synthesis of Pseudo-C2-symmetric Diamino Alcohols and Triamines for Use in HIV Protease Inhibitors (Articolo in rivista)

Type

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

Label

• Stereocontrolled Synthesis of Pseudo-C2-symmetric Diamino Alcohols and Triamines for Use in HIV Protease Inhibitors (Articolo in rivista) (literal)

Anno

• 2003-01-01T00:00:00+01:00 (literal)

Alternative label

• Bernardi, L.; Bonini, B. F.; Dessole, G.; Fochi, M.F.; Comes-Franchini, M.; Gavioli, S.; Ricci, A.; Varchi, G. (2003)
  Stereocontrolled Synthesis of Pseudo-C2-symmetric Diamino Alcohols and Triamines for Use in HIV Protease Inhibitors
  in Journal of organic chemistry
  (literal)

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

• Bernardi, L.; Bonini, B. F.; Dessole, G.; Fochi, M.F.; Comes-Franchini, M.; Gavioli, S.; Ricci, A.; Varchi, G. (literal)

Pagina inizio

• 1418 (literal)

Pagina fine

• 1425 (literal)

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

• 68 (literal)

Rivista

• Journal of organic chemistry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Titolo

• Stereocontrolled Synthesis of Pseudo-C2-symmetric Diamino Alcohols and Triamines for Use in HIV Protease Inhibitors (literal)

Abstract

• A new protocol is described for the stereocontrolled synthesis of pseudo-C2-symmetric core units of interest as candidates for HIV protease inhibition. Addition of unbranched and branched organolithium reagents to cyanohydrins from L-phenylalaninal and L-isoleucinal, followed by in situ reduction of the intermediate imines and CHT deprotection under MW irradiation, led to 1,3-diamino alcohols 6a and 8a as the major products in satisfactory to good yields. The first preparation of a previously unreported pseudo-C2-symmetric triamino derivative was accomplished expeditiously via high-yielding nitro-Mannich addition of the silylnitronate, from 2-phenyl-1-nitroethane, to the PMP imine derived from L-phenylalaninal. Reduction of the nitro group in the moderately unstable nitro diamine adduct, followed by chromatographic separation of the required diastereoisomer and CHT debenzylation under MW irradiation, led to the 2-PMP-protected triamine 19 isolated as a bis(sulfonamide) (literal)

Prodotto di

• Sintesi e caratterizzazione mediante metodologie chimiche innovative, di scaffold molecolari per l'individuazione di nuove molecole biologicamente attive. (PM.P03.011.002) (Modulo)
• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)

Autore CNR

• GRETA VARCHI (Unità di personale interno)

Incoming links:

Prodotto

• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)
• Sintesi e caratterizzazione mediante metodologie chimiche innovative, di scaffold molecolari per l'individuazione di nuove molecole biologicamente attive. (PM.P03.011.002) (Modulo)

Autore CNR di

• GRETA VARCHI (Unità di personale interno)

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

• Journal of organic chemistry (Rivista)