The synthesis of a series of 4-aza cross-conjugated cyclopentenones, inspired by the natural prostaglandin Δ12,14-15-deoxy-PGJ2 (5) is described. Using the 4-aza cyclopentenone 7, the installation of the α-side chain was performed using N-functionalisation, following a Boc-deprotection. The ω-side chain was then installed through a Baylis-Hillman type aldol reaction with trans-2-octenal. This afforded 11, the aza-analogue of 5. With this prostaglandin analogue in hand, a series of thiol adducts (14-16) were prepared. Included are activities for compounds 11 and 14-16 in relation to inhibition of the transcription factor NF-κB.

Conway, L., Riccio, A., Santoro, M.g., Evans, P. (2020). Synthesis of the 4-aza cyclopentenone analogue of Δ12,14-15-deoxy-PGJ2 and S-cysteine adducts. TETRAHEDRON LETTERS, 61(25) [10.1016/j.tetlet.2020.151969].

Synthesis of the 4-aza cyclopentenone analogue of Δ12,14-15-deoxy-PGJ2 and S-cysteine adducts

Riccio A;Santoro M. G.
;
2020-01-01

Abstract

The synthesis of a series of 4-aza cross-conjugated cyclopentenones, inspired by the natural prostaglandin Δ12,14-15-deoxy-PGJ2 (5) is described. Using the 4-aza cyclopentenone 7, the installation of the α-side chain was performed using N-functionalisation, following a Boc-deprotection. The ω-side chain was then installed through a Baylis-Hillman type aldol reaction with trans-2-octenal. This afforded 11, the aza-analogue of 5. With this prostaglandin analogue in hand, a series of thiol adducts (14-16) were prepared. Included are activities for compounds 11 and 14-16 in relation to inhibition of the transcription factor NF-κB.
2020
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore MED/07 - MICROBIOLOGIA E MICROBIOLOGIA CLINICA
English
Conway, L., Riccio, A., Santoro, M.g., Evans, P. (2020). Synthesis of the 4-aza cyclopentenone analogue of Δ12,14-15-deoxy-PGJ2 and S-cysteine adducts. TETRAHEDRON LETTERS, 61(25) [10.1016/j.tetlet.2020.151969].
Conway, L; Riccio, A; Santoro, Mg; Evans, P
Articolo su rivista
File in questo prodotto:
File Dimensione Formato  
Stachulski et al. 2018 fmc-2017-0217-3.pdf

solo utenti autorizzati

Descrizione: Stachulski et al. 2018
Tipologia: Documento in Post-print
Licenza: Copyright dell'editore
Dimensione 580.27 kB
Formato Adobe PDF
580.27 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/261565
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 2
  • ???jsp.display-item.citation.isi??? 2
social impact