737004-51-2Relevant academic research and scientific papers
Anti-Pneumocystis carinii and antiplasmodial activities of primaquine-derived imidazolidin-4-ones
Vale, Nuno,Collins, Margaret S.,Gut, Jiri,Ferraz, Ricardo,Rosenthal, Philip J.,Cushion, Melanie T.,Moreira, Rui,Gomes, Paula
, p. 485 - 488 (2008/09/18)
A series of primaquine-derived imidazolidin-4-ones were screened for their in vitro activity against Pneumocystis carinii and Plasmodium falciparum W2 strain. Most compounds were active against P. carinii above 10 μg/mL and displayed slight to marked acti
Reactivity of imidazolidin-4-one derivatives of primaquine: implications for prodrug design
Chambel, Paula,Capela, Rita,Lopes, Francisca,Iley, Jim,Morais, José,Gouveia, Luís,Gomes, José R.B.,Gomes, Paula,Moreira, Rui
, p. 9883 - 9891 (2007/10/03)
In contrast to peptide-based imidazolidin-4-ones, those synthesized from N-(α-aminoacyl) derivatives of the antimalarial drug, primaquine and ketones are unexpectedly stable in pH 7.4 at 37 °C. The kinetics of hydrolysis of primaquine-based imidazolidin-4
Imidazolidin-4-one derivatives of primaquine as novel transmission-blocking antimalarials
Araújo, Maria Jo?o,Bom, Joana,Capela, Rita,Casimiro, Catarina,Chambel, Paula,Gomes, Paula,Iley, Jim,Lopes, Francisca,Morais, José,Moreira, Rui,De Oliveira, Eliandre,Do Rosário, Virgílio,Vale, Nuno
, p. 888 - 892 (2007/10/03)
Imidazolidin-4-one derivatives of primaquine were synthesized as potential double prodrugs of the parent drug. The title compounds inhibit the development of the sporogonic cycle of Plasmodium berghei, affecting the appearance of oocysts in the midguts of the mosquitoes. The imidazolidin-4-ones are very stable, both in human plasma and in pH 7.4 buffer, indicating that they are active per se. Thus, imidazolidin-4-ones derived from 8-aminoquinolines represent a new entry in antimalarial structure - activity relationships.
Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)- dione derivatives of primaquine: Scope and limitations
Gomes, Paula,Araújo, Maria Jo?o,Rodrigues, Manuela,Vale, Nuno,Azevedo, Zélia,Iley, Jim,Chambel, Paula,Morais, José,Moreira, Rui
, p. 5551 - 5562 (2007/10/03)
The synthesis of imidazolidin-4-one derivatives of primaquine as potential antimalarial agents is described. The target compounds were synthesized in three steps: (i) condensation of (±)-primaquine with Nα- protected amino acids, (ii) removal of the Nα-protecting group, and (iii) reaction of the N-acylprimaquine with a carbonyl compound: acetone, three cyclic ketones and veratraldehyde. Using 2-formylbenzoic acid in the third step afforded 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones. All products were isolated in good to excellent yields. Whereas imidazolidin-4-ones were formed as mixtures of all possible diastereomers in equal amounts, 1H-imidazo[2,1-a] isoindole-2,5(3H,9bH)-diones were produced in a stereoselective fashion. The compounds hydrolyse very slowly (t1/2 5-30 d) in pH 7.4 buffer to release primaquine. These primaquine derivatives are being submitted to biological assays, and preliminary results of their antimalarial activity are quite encouraging.
