title: Thalidomide analogs from diamines: Synthesis and evaluation as inhibitors of TNF-alpha production.
abstract: 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.
authors.affiliation: Department of Chemistry, ICE, Federal University of Juiz de Fora.
authors.forename: Mauro Vieira
authors.initials: MV
authors.lastname: de Almeida
authors.forename: Francisco Martins
authors.initials: FM
authors.lastname: Teixeira
authors.forename: Marcus Vinicius Nora
authors.initials: MV
authors.lastname: de Souza
authors.forename: Giovanni Wilson
authors.initials: GW
authors.lastname: Amarante
authors.forename: Caio César de Souza
authors.initials: CC
authors.lastname: Alves
authors.forename: Sílvia Helena
authors.initials: SH
authors.lastname: Cardoso
authors.forename: Ana Márcia
authors.initials: AM
authors.lastname: Mattos
authors.forename: Ana Paula
authors.initials: AP
authors.lastname: Ferreira
authors.forename: Henrique Couto
authors.initials: HC
authors.lastname: Teixeira
mesh_terms: 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
chemical_list: 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