762301-51-9

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[4-[[2-(1,1-dimethylethyl)-6-methoxy-8-quinolinyl]amino]pentyl]-
• CAS NO: 762301-51-9
• Molecular Formula: C27H31N3O3
• Molecular Weight: 445.561
• Mol File: 762301-51-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[4-[[2-(1,1-dimethylethyl)-6-methoxy-8-quinolinyl]amino]pentyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[4-[[2-(1,1-dimethylethyl)-6-methoxy-8-quinolinyl]amino]pentyl]-(762301-51-9)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[4-[[2-(1,1-dimethylethyl)-6-methoxy-8-quinolinyl]amino]pentyl]-(762301-51-9)

Safety Data

• Hazardous Substances Data: 762301-51-9(Hazardous Substances Data)

Upstream product

• 59353-62-7 4-bromo-1-phthalimidopentane 
• 655250-13-8 2-tert-butyl-6-methoxy-8-quinolinamine 

Downstream Products

• 925934-33-4 (R)-{5-benzyloxycarbonylamino-1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]pentyl}carbamic acid benzyl ester 
• 925934-47-0 (S)-{1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]-2-(tritylsulfanyl)ethyl}carbamic acid tert-butyl ester 
• 925934-42-5 (S)-(2-(4-benzyloxyphenyl)-1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]ethyl)carbamic acid tert-butyl ester 
• 925934-45-8 (S)-{2-benzylsulfanyl-1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]ethyl}carbamic acid tert-butyl ester 
• 925934-43-6 (S)-{2-benzyloxy-1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]ethyl}carbamic acid tert-butyl ester 
• 925934-41-4 (S)-{1-[4-(2-tert-butyl-6-methoxy-8-quinolylamino)pentylcarbamoyl]-2-phenylethyl}carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis, antimalarial, antileishmanial, antimicrobial, cytotoxicity, and methemoglobin (MetHB) formation activities of new 8-quinolinamines

We report the synthesis, in vitro antiprotozoal (against Plasmodium and Leishmania), antimicrobial, cytotoxicity (Vero and MetHb-producing properties), and in vivo antimalarial activities of two series of 8-quinolinamines. N1-{4-[2-(tert-Butyl)-6-methoxy-8-quinolylamino]pentyl}-(2S/2R)-2-aminosubstitutedamides (21-33) and N1-[4-(4-ethyl-6-methoxy-5-pentyloxy-8-quinolylamino)pentyl]-(2S/2R)-2-aminosubstitutedamides (51-63) were synthesized in six steps from 6-methoxy-8-nitroquinoline and 4-methoxy-2-nitro-5-pentyloxyaniline, respectively. Several analogs displayed promising antimalarial activity in vitro against Plasmodium falciparum D6 (chloroquine-sensitive) and W2 (chloroquine-resistant) clones with high selectivity indices versus mammalian cells. The most promising analogs (21-24) also displayed potent antimalarial activity in vivo in a Plasmodium berghei-infected mouse model. Most interestingly, many analogs exhibited promising in vitro antileishmanial activity against Leishmania donovani promastigotes, and antimicrobial activities against a panel of pathogenic bacteria and fungi. Several analogs, notably 21-24, 26-32, and 60, showed less MetHb formation compared to primaquine indicating the potential of these compounds in 8-quinolinamine-based antimalarial drug development.

Discovery of a Bulky 2-tert-Butyl Group Containing Primaquine Analogue That Exhibits Potent Blood-Schizontocidal Antimalarial Activities and Complete Elimination of Methemoglobin Toxicity

To eliminate an unwarranted metabolic pathway of the quinoline ring, a set of two compounds, where C-2 position of the antimalarial drug primaquine is blocked by metabolically stable bulky alkyl group are synthesized. Compound 2 [R = C(CH3)3] of the series has produced excellent antimalarial efficacy against P. berghei and highly virulent multidrug-resistant P. yoelii nigeriensis strain in vivo. Compound 2 was also evaluated for methemoglobin (MetHb) toxicity. This study describes the discovery of a highly potent blood-schizontocidal antimalarial analogue 2, completely devoid of MetHb toxicity.