737004-41-0

Upstream product

• 90-34-6 Primaquine 
• 3674-06-4 Boc-Phe-ONSu 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 737004-56-7 3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-3-benzyl-1,4-diazaspiro[4.5]decan-2-one 
• 737004-51-2 3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-3-benzyl-1,4-diazaspiro[4.4]nonan-2-one 
• 737004-39-6 N-{7-[(6-methoxyquinolin-8-yl)amino]-3-aza-1-benzyl-2-oxooctyl}carbamic acid tert-butyl ester 

Downstream Products

• 737004-56-7 3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-3-benzyl-1,4-diazaspiro[4.5]decan-2-one 
• 737004-46-5 3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-5-benzyl-2,2-dimethylimidazolidin-4-one 
• 1160640-43-6 C₃₁H₄₁N₅O₅ 
• 737004-51-2 3-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-3-benzyl-1,4-diazaspiro[4.4]nonan-2-one 

Relevant academic research and scientific papers

Novel potent metallocenes against liver stage malaria

Novel conjugates of the antimalarial drug primaquine (compound 1) with ferrocene, named primacenes, have been synthesized and screened for their activities against blood stage and liver stage malaria in vitro and host-vector transmission in vivo. Both transmission-blocking and blood-schizontocidal activities of the parent drug were conserved only in primacenes bearing a basic aliphatic amine group. Liver stage activity did not require this structural feature, and all metallocenes tested were comparable to or better than primaquine in this regard. Remarkably, the replacement of primaquine's aliphatic chain by hexylferrocene, as in compound 7, led to a ～45-fold-higher level activity against liver stage parasitemia than that of primaquine. Copyright

Reactivity of imidazolidin-4-one derivatives of primaquine: implications for prodrug design

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

Anti-Pneumocystis carinii and antiplasmodial activities of primaquine-derived imidazolidin-4-ones

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

Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)- dione derivatives of primaquine: Scope and limitations

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.