2346-98-7

Basic information

• Product Name: (+/-)-epilupinamine
• CAS NO: 2346-98-7
• Molecular Weight: 168.282
• Mol File: 2346-98-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (+/-)-epilupinamine(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-epilupinamine(2346-98-7)
• EPA Substance Registry System: (+/-)-epilupinamine(2346-98-7)

Safety Data

• Hazardous Substances Data: 2346-98-7(Hazardous Substances Data)

Upstream product

• 29944-19-2 (+/-)-(5R^*,6R^*)-1-azabicyclo<4.4.0>decane-5-carbonitrile 
• 145801-16-7 1-(2-ethoxycarbonylethyl)-2-cyanomethylenepiperidine 
• 145801-17-8 1-(3-hydroxypropyl)-2-cyanomethylenepiperidine 
• 145801-19-0 1-azabicyclo<4.4.0>dec-5-ene-5-carbonitrile 
• 58576-26-4 1-(2-ethoxycarbonylethyl)piperidine-2-thione 
• 13070-01-4 piperidine-2-thione 
• 29944-19-2 (+/-)-(5R^*,6S^*)-1-azabicyclo<4.4.0>decane-5-carbonitrile 
• 10248-22-3 (+/-)-N-Lupinyl-phthalimid 
• 111277-80-6 (1R,9aR)-4-Oxo-octahydro-quinolizine-1-carboxylic acid amide 
• 23506-89-0 (1S,9aR)-1-(aminomethyl)-(octahydro-2H-quinolizine) 
• 486-70-4 lupinine 
• 5280-36-4 (9aR)-1t-(toluene-4-sulfonyloxymethyl)-(9ar)-octahydro-quinolizin 
• 10248-22-3 2-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-1H-isoindol-1,3(2H)-dione 

Downstream Products

• 68676-72-2 N-[(9aR)-(9ar)-octahydro-quinolizin-1t-ylmethyl-benzamide 
• 137739-81-2 N-lupinyl-2-nitroaniline 
• 68676-73-3 4-Nitro-N-[(1S,9aR)-1-(octahydro-quinolizin-1-yl)methyl]-benzamide 
• 905557-27-9 N-[3-hydroxy-4-[[((1S,9aR)-octahydro-2H-quinolizin-1-yl)methylamino]methyl]phenyl]acetamide 
• 1379467-44-3 3-(2,5-dimethoxyphenyl)-9-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1379467-43-2 3-(2,4-dimethoxyphenyl)-9-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1379467-41-0 2-methyl-9-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1379467-38-5 3-(4-methoxyphenyl)-9-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1379467-39-6 3-(3-methoxyphenyl)-9-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1379467-40-9 3-(2-methoxyphenyl)-9-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1379467-42-1 2-methyl-3-(2-methoxyphenyl)-9-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 

Relevant articles and documents

Synthesis and comparison of antiplasmodial activity of (+), (-) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline

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 4-AMINOQUINOLINE DERIVATIVES AS ANTIMALARIALS

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

(±)-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.