Synthesis of flutamide-conjugates

  • Bioorg Med Chem Lett. 2020 Nov 1;30(21):127507. doi: 10.1016/j.bmcl.2020.127507.
Julio César Medina-Rojas  1 ,  Irving Osiel Castillo-Rodríguez  1 ,  Elena Martínez-Klimova  2 ,  Teresa Ramírez-Ápan  1 ,  Simón Hernández-Ortega  1 ,  Marcos Martínez-García  3
Affiliations
  • 1. Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Circuito Exterior, Coyoacán, C.P. 04510, México, D.F., México.
  • 2. Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Circuito Interior, Coyoacán, C.P. 04510, México, D.F., México.
  • 3. Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Circuito Exterior, Coyoacán, C.P. 04510, México, D.F., México. Electronic address: [email protected].
PMID: 32866675 DOI: 10.1016/j.bmcl.2020.127507
Abstract

In this paper, we designed and extended modification basing on the flutamide structure. A series of flutamide-conjugates were obtained with methyl bromoacetate and ethylenediamine. Through the synthesis of two conjugates with 3,5-bis(dodecyloxy)benzoate derivatives, these flutamide conjugates were tested for Anticancer activity. Among the compounds tested, the flutamide-conjugates showed good inhibition activity against Cancer cell lines U-251, PC-3 and K-562. The conjugates showed a better inhibitory effect than free flutamide and did not show activity against normal COS-7 monkey kidney fibroblast cells. It was also observed that the flutamide conjugates had an inhibitory effect against human colorectal adenocarcinoma HCT-15.

Keywords
Antiproliferative; Cancer; Flutamide conjugates; PC-3 inhibitors; Therapy.