title: Synthesis and biological evaluation against Mycobacterium tuberculosis and Leishmania amazonensis of a series of diaminated terpenoids.
abstract: We report the synthesis of a series of diaminated terpenoids containing, as side-chain of the diamine core, the "head-to-tail" prenyl derivatives, with amino amino spacers of variable length. In vitro biological activity of these compounds was evaluated against Mycobacterium tuberculosis and Leishmania amazonensis, and the structure-activity relationships are discussed. Different biological results were observed depending on the terpenic side-chain length. The best results were obtained for trans,trans-farnesol derivatives. Moreover, these results demonstrated that the stereochemistry of the double bond could play an important role in determining antitubercular and antileishmanial activities of these compounds.
authors.affiliation: Instituto de Física e Química, Universidade Federal de Itajubá, 37500-903, Itajubá-MG, Brazil.
authors.forename: Dijovani Batista
authors.initials: DB
authors.lastname: Dos Reis
authors.affiliation: Instituto de Física e Química, Universidade Federal de Itajubá, 37500-903, Itajubá-MG, Brazil.
authors.forename: Thalita Cristina Alves
authors.initials: TCA
authors.lastname: Souza
authors.affiliation: Instituto de Pesquisas Clínicas Evandro Chagas, Departamento de Bacteriologia, Fundação Oswaldo Cruz, Av. Brasil, 4365, Manguinhos, Rio de Janeiro, Brazil.
authors.forename: Maria Cristina S
authors.initials: MCS
authors.lastname: Lourenço
authors.affiliation: Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora-MG, Brazil.
authors.forename: Mauro Vieira
authors.initials: MV
authors.lastname: de Almeida
authors.affiliation: Departamento de Biologia Geral, Universidade Estadual de Ponta Grossa, Av. Gen. Carlos Cavalcanti, 4746, Uvaranas, Ponta Grossa-PR, Brazil.
authors.forename: Adriano
authors.initials: A
authors.lastname: Barbosa
authors.affiliation: Departamento de Biologia Geral, Universidade Estadual de Ponta Grossa, Av. Gen. Carlos Cavalcanti, 4746, Uvaranas, Ponta Grossa-PR, Brazil.
authors.forename: Iriane
authors.initials: I
authors.lastname: Eger
authors.affiliation: Instituto de Física e Química, Universidade Federal de Itajubá, 37500-903, Itajubá-MG, Brazil. Electronic address: mauriciosaraiva@unifei.edu.br.
authors.forename: Mauricio Frota
authors.initials: MF
authors.lastname: Saraiva
mesh_terms: D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D003959:Diamines / Q000138:chemical synthesis* / Q000494:pharmacology*; D015195:Drug Design; D007894:Leishmania mexicana / Q000187:drug effects* / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects* / Q000254:growth & development; D021261:Parasitic Sensitivity Tests; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000981:Antiprotozoal Agents; D000995:Antitubercular Agents; D003959:Diamines; D013729:Terpenes
keywords: Diamine; Leishmaniasis; Terpenoid; Tuberculosis