215592-20-4

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N-(7-Chloro-4-quinolinyl)-N'-[2-[(7-chloro-4-quinolinyl)aMino]ethyl]-1,2-ethanediaMine shows anti-malarial activity due to its bis(quinoline) structure. In addition,

Upstream product

• 86-98-6 4,7-dichloroquinoline 
• 111-40-0 3-azapentane-1,5-diamine 

Relevant academic research and scientific papers

Bisquinolines. 2. Antimalarial N,N-Bis(7-chloroquinolin-4- yl)heteroalkanediamines

N,N-Bis(7-chloroquinolin-4-yl)heteroalkanediamines 1-11 were synthesized and screened against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. These bisquinolines had IC50 values from 1 to 100 nM against P. falciparum in vitro. Six of the 11 bisquinolines were significantly more potent against the chloroquine-resistant W2 clone compared to the chloroquine-sensitive D6 clone. For bisquinolines 1-11 there was no relationship between the length of the bisquinoline heteroalkane bridge and antimalarial activity and no correlation between in vitro and in vivo antimalarial activities. Bisquinolines with alkyl ether and piperazine bridges were substantially more effective than bisquinolines with alkylamine bridges against P. berghei in vivo. Bisquinolines 1-10 were potent inhibitors of hematin polymerization with IC50 values falling in the narrow range of 5-20 μM, and there was a correlation between potency of inhibition of hematin polymerization and inhibition of parasite growth. Compared to alkane- bridged bisquinolines (Vennerstrom et al., 1992), none of these heteroalkane- bridged bisquinolines had sufficient antimalarial activity to warrant further investigation of the series.

Synthesis and in vitro antimalarial activity of a series of bisquinoline and bispyrrolo[1,2a]quinoxaline compounds

Series of bisquinolines 4-15 and bispyrrolo[1,2a]quinoxalines 16-20 containing various polyamine linkers were synthesized. The aqueous solubility and distribution coefficient were experimentally determined. The compounds were screened for antimalarial activity alongside chloroquine against D10 and Dd2 strains of Plasmodium falciparum. The growth inhibitory effects of biscompounds 4-9 were assessed against various cancer cell lines. The aqueous solubility was found to increase with an increase in potential proton.ation sites. Bisquinolines 8 and 9 featuring triethylenetetramine and N,N′-bis(3- aminopropyl)ethylene-diamine linkers, respectively, were the most active of all synthesized compounds. They were found as potent as chloroquine against D10 but significantly more potent against the Dd2 strain, with good selectivity towards parasitic cells. Compound 4 containing a diethylenetriamine bridge displayed the most important anticancer activity of the series, and was a more effective antiproliferative inhibitor than etoposide against all three TK10, UACC62 and MCF7 cancer cell lines.

BIAMINOQUINOLINES AND NANOFORMULATIONS FOR CANCER TREATMENT

The present invention provides bisaminoquinoline compounds of Formula (I). The present invention also provides nanocarriers comprising compounds of the present invention, and methods of using the nanocarriers for treating diseases and imaging.

Potent Antimalarial Activity of Two Arenes Linked with Triamine Designed to Have Multiple Interactions with Heme

Based on the idea that compounds designed to exhibit high affinity for heme would block hemozoin formation, a critical heme-detoxification process for malarial parasites, we synthesized a series of compounds with two π-conjugated moieties at terminal amino groups of triamine. These compounds exhibited moderate to high antimalarial activities in vitro toward both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum. In a P. berghei-infected mouse model, 3a and 12a showed potent antimalarial activities compared to artesunate, as well as a prolonged duration of antimalarial effect. We found a good correlation between protective activity against hemin degradation and antimalarial activity. Compounds 8b and 3a strongly inhibited hemozoin formation catalyzed by heme detoxification protein.

Antiplasmodial activity and cytotoxicity of bis-, tris-, and tetraquinolines with linear or cyclic amino linkers

Bisquinoline heteroalkanediamines were structurally modified in order to study the effects of enhanced bulkiness and rigidity on both their activity on strains of Plasmodium falciparum expressing different degrees of chloroquine (CQ) resistance and their