91049-90-0

Usage

Uses

Used in Agricultural Applications:
Chlorolupinine is used as a biopesticide for its insecticidal and pesticidal properties, offering an alternative to synthetic chemicals for pest control in farming. Its natural origin and effectiveness against various pests make it a favorable option for integrated pest management strategies.
Used in Pharmaceutical Applications:
Chlorolupinine is used as a potential anticancer agent due to its ability to target and inhibit the growth of cancer cells. Chlorolupinine's unique structure and bioactivity suggest it may contribute to the development of novel therapeutics for cancer treatment, warranting further research into its mechanisms of action and potential synergistic effects with existing treatments.
Used in Anti-Inflammatory Applications:
Leveraging its anti-inflammatory properties, Chlorolupinine is utilized in the development of medications aimed at reducing inflammation. This can be particularly beneficial in conditions where inflammation is a significant factor, offering a natural alternative to synthetic anti-inflammatory drugs.

Upstream product

• 10248-30-3 lupinine 
• 16100-91-7 cis carbethoxy-1 octahydro-1,2,3,6,7,8,9,10-4H-pyrido<1,2-a>pyridine 
• 10297-06-0 1-chloro-5-hexyne 
• 90675-48-2 7-Chlor-heptin-⁽²⁾-saeure-ethylester 
• 90642-54-9 ethyl 7-iodo-2-heptynoate 
• 7635-52-1 3,4,6,7,8,9-hexahydro-2H-quinolizine-1-carboxylic acid ethyl ester 

Downstream Products

• 10248-22-3 (+/-)-N-Lupinyl-phthalimid 

Relevant academic research and scientific papers

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.