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Synthesis and anti-inflammatory activity of 8H-1-thia-8- aza-dibenzo[e, h]azulenes


Ozimec Landek, Ivana; Pešić, Dijana; Merćep, Mladen; Stanić, Barbara; Mesić, Milan
Synthesis and anti-inflammatory activity of 8H-1-thia-8- aza-dibenzo[e, h]azulenes // Journal of heterocyclic chemistry (2011) (znanstveni, prihvaćen)


Naslov
Synthesis and anti-inflammatory activity of 8H-1-thia-8- aza-dibenzo[e, h]azulenes

Autori
Ozimec Landek, Ivana ; Pešić, Dijana ; Merćep, Mladen ; Stanić, Barbara ; Mesić, Milan

Vrsta, podvrsta
Radovi u časopisima, znanstveni

Izvornik
Journal of heterocyclic chemistry (2011)

Status rada
Prihvaćen

Ključne riječi
8H-1-thia-8-aza-dibenzo[e; h]azulenes; N-protection; anti-inflammatory activity

Sažetak
Synthesis of a novel class of fused hetero-tetracyclic compounds, 8H-1-thia-8-aza-dibenzo[e, h]azulenes (VII), is described. Starting N-benzoyl-protected 5H-dibenzo[b, f]azepine (XI, PG = Bz) was oxidized to 5-benzoyl-10, 11- epoxy-10, 11-dihydro-5H-dibenzo[b, f]azepine (2) which subsequently rearranged in Lewis acid induced epoxide ring opening to give 5-benzoyl-5, 11-dihydro-10H- dibenzo[b, f]azepin-10-one (3). Vilsmeier reaction of 3 provided gama-chlorovinyl aldehyde 4 that readily cyclized with ethyl 2-mercaptoacetate to form dibenzazepino[4, 5]-fused thiophene structure 5. Further transformation of substituent at C-2 position of 5 and N- deprotection led to final aminoalkoxy derivatives 9. All compounds with tetracyclic skeleton were tested in vitro for their anti-inflammatory activity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



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Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus