15527-89-6Relevant academic research and scientific papers
Oxidative deamination of tetrahydroanabasine with o-quinones: An easy entry to lupinine, sparteine, and anabasine
Wanner, Martin J.,Koomen, Gerrit-Jan
, p. 5581 - 5586 (1996)
A mild oxidative deamination reaction of tetrahydroanabasine O-methyloxime 17 is described, making use of an o-quinone that is based on topaquinone (TPQ, 11), the cofactor that is present in copper-containing amine oxidases. In situ ring closure of the oxidation product produced double functionalized quinolizidine 5, containing an enamine functionality with excellent reactivity. From this quinolizidine 5 a variety of biogenetically related lupin alkaloids were prepared: lupinine (7) and aminolupinane (8) via reductive sequences and sparteine (9) via a condensation reaction with dehydropiperidine 1. The configurationally more favorable trans isomers epilupinine (25) and β-isosparteine (10) were formed when more drastic reaction conditions were used for oxime hydrolysis. Anabasine (4) and a new 5-piperidylanabasine derivative 6 were formed by an unexpected acid catalyzed ring transformation reaction, whereby the pyridine ring was formed via oxime-induced aromatization. The stereochemistry of the reaction products and the biogenetic implications are discussed.
Synthesis and comparison of antiplasmodial activity of (+), (-) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline
Rusconi, Chiara,Vaiana, Nadia,Casagrande, Manolo,Basilico, Nicoletta,Parapini, Silvia,Taramelli, Donatella,Romeo, Sergio,Sparatore, Anna
, p. 5980 - 5985 (2012/11/06)
Recently the N-(-)-lupinyl-derivative of 7-chloro-4-aminoquinoline ((-)-AM-1; 7-chloro-4-{N-[(1S,9aR)(octahydro-2H-quinolizin-1-yl)methyl]amino} quinoline) showed potent in vitro and in vivo activity against both Chloroquine susceptible and resistant strains of Plasmodium falciparum. However, (-)-AM-1 is synthesized starting from (-)-lupinine, an expensive alkaloid isolated from Lupinus luteus whose worldwide production is not sufficient, at present, for large market purposes. To overcome this issue, the corresponding racemic compound, derived from synthetic (±)-lupinine was considered a cheaper alternative for the development of a novel antimalarial agent. Therefore, the racemic and the 7-chloro-4-(N-(+)-lupinyl)aminoquinoline ((±)-AM-1; (+)-AM-1) were synthesized and their in vitro antimalarial activity and cytotoxicity compared with those of (-)-AM-1. The (+)-lupinine required for the synthesis of (+)-AM-1 was obtained through a not previously described lipase catalyzed kinetic resolution of (±)-lupinine. In terms of antimalarial activity, (±)-AM1 and (+)-AM1 demonstrated very good activity in vitro against both CQ-R and CQ-S strains of P. falciparum (range IC50 16-35 nM), and low toxicity against human normal cell lines (therapeutic index >1000), comparable with that of (-)-AM1. These results confirm that the racemate (±)-AM1 could be considered as a potential antimalarial agent, ensuring a decrease of costs of synthesis compared to (-)-AM1.
New flavonoid-containing derivatives of lupinine
Bondarenko,Frasinyuk,Galaev,Vinogradova
experimental part, p. 234 - 237 (2012/09/07)
An oxazine ring was annelated to benzopyran-4-one and benzopyran-2-one cores by reacting 7-hydroxyisoflavones and 7-hydroxycoumarins with lupinylamine and formalin. The new derivatives 9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin- 4-one and 9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-2-one containing a lupinine moiety in the 9-position were prepared.
NEW 4-AMINOQUINOLINE DERIVATIVES AS ANTIMALARIALS
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Page/Page column 8-9, (2008/06/13)
New 4-aminoquinoline derivatives having the general formula (I) wherein R, M, X, Y and T have the meaning described in the specification, as potent antimalarials active also on chloroquine-resistant Plasmodium falciparum malaria strains.
New syntheses of (±)-lamprolobine and (±)-epilamprolobine
Michael,Jungmann
, p. 10211 - 10220 (2007/10/02)
(±)-Lamprolobine 1 and (±)-epilamprolobine 4 were prepared by a route featuring sulphide contraction of thiolactam 7 with bromoacetonitrile to give vinylogous cyanamide 8, reduction and ring closure to the unsaturated quinolizidine 11, and selective reduction of the latter to set up appropriate stereochemistry for the target alkaloids.
Biomimetic Synthesis of Quinolizidine Alkaloids
Wanner, Martin J.,Koomen, Gerrit-Jan
, p. 8431 - 8442 (2007/10/02)
Quinolizidine alkaloids are synthesized from glutarimide ylides via a piperidine ring transformation that is based on the lupinine biosynthesis.A short enantioselective bispiperidine synthesis using R-phenylglycinol as a chiral precursor is described.Key
