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Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine: scope and limitations
- Source :
-
Tetrahedron . Jun2004, Vol. 60 Issue 26, p5551-5562. 12p. - Publication Year :
- 2004
-
Abstract
- 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. [Copyright &y& Elsevier]
- Subjects :
- *AMINES
*QUINOLINE
*KETONES
*AMINO acids
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 60
- Issue :
- 26
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 13292227
- Full Text :
- https://doi.org/10.1016/j.tet.2004.04.077