Thalidomide analogs from diamines: Synthesis and evaluation as inhibitors of TNF-alpha production.
Fourteen thalidomide analogs bearing two phthalimido units were prepared in high yields (83-94%) by condensation of different diamines with phthalic or 3-nitrophthalic anhydride. An in vitro investigation of the compounds as inhibitors of the TNF-alpha production was performed. The inhibition was higher for compounds bearing amino and nitro groups and was modulated by increasing the size of the spacers between the phthalimide groups.
de Almeida
Mauro Vieira
MV
Department of Chemistry, ICE, Federal University of Juiz de Fora.
Teixeira
Francisco Martins
FM
de Souza
Marcus Vinicius Nora
MV
Amarante
Giovanni Wilson
GW
Alves
Caio César de Souza
CC
Cardoso
Sílvia Helena
SH
Mattos
Ana Márcia
AM
Ferreira
Ana Paula
AP
Teixeira
Henrique Couto
HC
D020533:Angiogenesis Inhibitors / Q000494:pharmacology; D003959:Diamines / Q000737:chemistry*; D007166:Immunosuppressive Agents / Q000494:pharmacology; D007917:Leprostatic Agents / Q000494:pharmacology; D010796:Phthalic Anhydrides / Q000737:chemistry; D010797:Phthalimides / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013792:Thalidomide / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000378:metabolism
D020533:Angiogenesis Inhibitors; D003959:Diamines; D007166:Immunosuppressive Agents; D007917:Leprostatic Agents; D010796:Phthalic Anhydrides; D010797:Phthalimides; D014409:Tumor Necrosis Factor-alpha; C037431:phthalimide; D013792:Thalidomide; C087675:3-nitrophthalic anhydride; C043103:phthalic anhydride