Synthesis, electrochemical studies and anticancer activity of ferrocenyl oxindoles.
A series of (E) and (Z)-ferrocenyl oxindoles were prepared by coupling substituted oxindoles to ferrocenylcarboxyaldehyde in the presence of morpholine as a catalyst. The redox behavior of these isomers was determined by cyclic voltammetry. The effects of the oxindole derivatives on the migration of human breast cancer cells were evaluated using the wound-healing assay and the Boyden chamber cell-migration assay. The most potent Z isomers 11b (IC(50) = 0.89 microM), 12b (IC(50) = 0.49 microM) and 17b (IC(50) = 0.64 microM) could represent attractive new lead compounds for further development for cancer therapy.
Silva
Bárbara V
BV
Instituto de Química-CT, Bloco A, Universidade Federal do Rio de Janeiro, Cidade Universitária, 21945-970, Rio de Janeiro, RJ, Brazil. barbara.iq@gmail.com
Ribeiro
Núbia M
NM
Vargas
Maria D
MD
Lanznaster
Maurício
M
Carneiro
José Walkimar de M
JW
Krogh
Renata
R
Andricopulo
Adriano D
AD
Dias
Luiz C
LC
Pinto
Angelo C
AC
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D001943:Breast Neoplasms / Q000188:drug therapy; D002384:Catalysis; D045744:Cell Line, Tumor; D055664:Electrochemical Techniques; D005260:Female; D005296:Ferrous Compounds / Q000737:chemistry*; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D007536:Isomerism; D000075163:Metallocenes; D009025:Morpholines / Q000737:chemistry; D010084:Oxidation-Reduction; D000078183:Oxindoles
D000970:Antineoplastic Agents; D005296:Ferrous Compounds; D007211:Indoles; D000075163:Metallocenes; D009025:Morpholines; D000078183:Oxindoles; C022960:2-oxindole; C037574:morpholine; C004998:ferrocene