| Author | Santos, Cláudio Eduardo Rodrigues | |
| Author | Leon, Leonor L. | |
| Author | Bortoluzzi, Adailton J. | |
| Author | Cavalheiro, Marilene Marcuzzo Canto | |
| Author | Machado, Gérzia C. | |
| Author | Echevarria, Aurea | |
| Access date | 2016-08-25T12:32:19Z | |
| Available date | 2016-08-25T12:32:19Z | |
| Document date | 2013 | |
| Citation | SANTOS, Cláudio Eduardo Rodrigues; et al. Synthesis, antileishmanial activity and structureeactivity relationship of 1-N-X-phenyl-3-N0 -Y-phenyl-benzamidines. European Journal of Medicinal Chemistry, v.67, p.166-174, Sept. 2013. | pt_BR |
| ISSN | 0223-5234 | pt_BR |
| URI | https://www.arca.fiocruz.br/handle/icict/15389 | |
| Language | eng | pt_BR |
| Publisher | Elsevier | pt_BR |
| Rights | restricted access | |
| Subject in Portuguese | Leishmania braziliensis | pt_BR |
| Subject in Portuguese | Leishmania | pt_BR |
| Title | Synthesis, antileishmanial activity and structure-activity relationship of 1-N-X-phenyl-3-N'-Y-phenyl-benzamidines | pt_BR |
| Type | Article | |
| DOI | 10.1016/j.ejmech.2013.06.040 | |
| Abstract | Two series of N,N'-diphenyl-benzamidines were synthesized as part of a study to search potential new drugs with antileishmanial activity. These compounds were obtained by anilides in PCl5 halogenation reaction with generation in situ of the corresponding benzimidoyl chlorides, and subsequently treatment with adequate anilines. The series I showed expressive results of antileishmanial activity, highlighted the compounds 9a with IC50 = 81.28 μM (log IC50 = 1.91 μM) against Leishmania chagasi, 8e with IC50 = 26.30 (log IC50 = 1.52 μM) against Leishmania braziliensis. From the results obtained from SAR study (series I), the series II was planned from Craig 2-dimensional map, in which was possible the discovery of the potent compounds, 9v and 9j with IC50 = 12.60 μM (log IC50 = 1.10 μM) and 13.00 μM (log IC50 = 1.11 μM), respectively, against Leishmania amazonensis. The results obtained from the SAR and QSAR studies indicated the best results when electron-donor groups in the ring attached to amidinic carbon, unlike when electron-withdrawing groups at the phenyl-N ring showing inhibitory activity increased. Furthermore, the QSAR model obtained indicated the hydrophobicity as a fundamental property for antileishmanial activity presented by these series. | pt_BR |
| Affilliation | Universidade Federal Rural do Rio de Janeiro. Instituto de Ciências Exatas. Departamento de Química. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Departamento de Imunologia. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | Universidade Federal de Santa Catarina. Departamento de Química. Florianópolis, SC, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Departamento de Imunologia. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Departamento de Imunologia. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Affilliation | Universidade Federal Rural do Rio de Janeiro. Instituto de Ciências Exatas. Departamento de Química. Rio de Janeiro, RJ, Brasil. | pt_BR |
| Subject | N,N0 -Diphenyl-benzamidines | pt_BR |
| Subject | Leishmania amazonensis | pt_BR |
| Subject | Leishmania chagasi | pt_BR |
| Subject | Leishmania braziliensis | pt_BR |
| Subject | QSAR | pt_BR |
| Subject | Hansch model | pt_BR |
| Embargo date | 2030-01-01 | |
