6-methoxy-8-aminoquinoline

Trachelantamine, according to Syrneva, has a weak atropine-like action and also produces local anaesthesia. Its hydrolytic product, trache-lantamidine, which is structurally identical with tsoretronecanol, yields a p-aminobenzoyl derivative of -which the crystalline hydrochloride, m.p. 230-2°, is said to be as potent a local anaesthetic as cocaine hydrochloride. The chloro- -heliotridane (p. 606) formed by the aetion of thionyl ehloride on trachelantamidine reacts with 6-methoxy-8-aminoquinoline to form 6-methoxy-8-(pseMdoheliotridylamino)-quinoline,... 

Bromo-l-phthalimidopentane 3 was obtained in 72-82 g yield by refluxing 92 g of 1,4-dibromopentane 1, 55.5 g of potassium phthalimide 2, and 200 mL dry acetone on a steam bath for 30 h. Compound 3 (30 g) and 42 g 6-methoxy-8-aminoquinoline 4 refluxed at 130-135 °C for 6 h, extracted with benzene to separate insoluble 6-methoxy-8-aminoquinoline hydrobromide, the residue from evaporation of the benzene was refluxed with stirring with 100 mL of an alcoholic solution of 6 g hydrazine hydrate for 4 h, the solution was concentrated, made acidic to Congo red with 8 N hydrochloric acid, filtered, and washed with boiling water. The combined filtrate and washings was concentrated, made alkaline, extracted with benzene, and distilled in vacuo to give 20.5 g primaquine 6, which was treated with 19 mL 85% phosphoric acid in absolute ethanol, formed 42.5% primaquine diphosphate. 

A membrane-permeant form of Quin-2 (systematic name 2-[(2-amino-5-methylphenoxy)methyl]-6-methoxy - 8 - aminoquinoline - A,A,A, A - tetraacetate) which upon binding of calcium ion results in fluorescence. See Fura-2... 

Primaquine Primaquine, 8-[(4-amino-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.4), is made from 6-methoxy-8-nitroquinoline (37.1.2.1), which is synthesized in a Skraup reaction from 4-methoxy-2-nitroaniline and glycerol in the presence of sulfuric acid. The nitro group in this compound is reduced to make 6-methoxy-8-aminoquinoline (37.1.2.2). Alkylating the amino group with 4-bromo-l-phthalimidopentane gives 8-[(4-phthalimido-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.3), the hydrazi-nolysis of which removes the phthalimide protection, giving primaqnine [28,29]. 

The presence of alkyl groups or chains can also influence the biological activity of a substrate or a drug. An interesting case is the antimalarial compounds derived from 6-methoxy-8-aminoquinoline (1-29) (primaquine... 

Other Names 2-[(2-Amino-5-methylphenoxy)meth-yl]-6-methoxy-8-aminoquinoline-A,A,A, A -tetraacetic... 

CA Index Name Glycine, A-[2-[(acetyloxy)methoxy]-2-oxoethyl] -N- [2- [ [8- [bis [2- [(acetyloxy)methoxy]-2-ox-oethyl]amino]-6-methoxy-2-quinolinyl]methoxy]-4-methylphenyl]-, (acetyloxy)methyl ester Other Names 2-[(2-Amino-5-methylphenoxy)meth-yl]-6-methoxy-8-aminoquinoline-A,A,A, A -tetraacetic acid tetrakis(acetoxymethyl ester) 2- [2-Bis(carboxy-methyl)amino-5-methylphenoxy]-methyl -6-methoxy-8-bis(carboxymethyl)aminoquinoline tetrakis(acetoxy-methyl) ester Quin 2 acetoxymethyl ester Quin 2 AM Quin 2 AM ester... 

Pyrrolizidine halides have been used as starting compounds for the synthesis of physiologically active agents, such as 6-methoxy-8-(pseudoheliotridyl)aminoquinoline (160a)102 and various other ter-... 

Cyclocondensation routes also provide access to pyrimidines. 2,3-Disubstituted pyrido[2,3-/i]-quinazolin-4(3//)-ones are obtained via cyclocondensation of 5-aminoquinoline-6-caiboxylic acid with acid chlorides <02SC235>. 5,6,8-Trialkyl-7-methoxy-2-aminoquinazolines are obtained from 1,3-dimethoxybenzenes via cyclocondensation of intermediate dihydrobenzenes with guanidine carbonate <02TL3295>. Diastereoselective intramolecular hetero Diels-Alder cyclization of a pyrazole carboxaldehyde condensed onto 1,3-dimethylbarbituric acid (101) gave polycyclic heterocycle 102 <02T531>. An efficient one-step synthesis of cyclobutene-annelated pyrimidinones 103 from methyl 2-chloro-2-cyclopropylideneacetate and amidines has been... 

Similarly, 4,7-dimethoxy-8-aminoquinoline reacts at 120°C with hydrazine-hydrate in 73% yield to give 4-hydrazino-7-methoxy-8-aminoquinoline (87MI1). 5-Methoxypyrimido-[5,4-e]-l,2,4-triazine is aminated by ammonia at -70°C to the 5-amino analogue (87JHC1657). 

In an endeavour to discover compounds with better activity and lesser toxicity than primaquine, two chemical approaches have been followed to develop a prodrug of primaquine. The first approach involves introduction of small peptide units linked covalently to the terminal amino group of the side chain [61]. Alternatively, substituents like sulphonyl, aminoacyl, glucopyranosyl, galactopyranosyl, mannopy-ranosyl and cyclic/open chain enaminone groups may be attached to the terminal amine of the side chain. The second approach is concerned with the modification of the side chain attached to the amino group of 8-amino-6-methoxyquinoline. Thus the synthesis of variety of 6-methoxy-8-(substituted) aminoquinolines was carried out, of which N -(3-acetyl-4,5-dihydro-2-furanyl-N -(6-methoxy-8-quinolinyl)-l,4-pen-MeO... 

Attempts to improve selectivity and sensitivity of spectrophotometric measurements by using new chromogenic reagents, e.g. of 2-(5-nitro-2-pyridylazo)-5-(A -propyl-A-sulfopropylamino)phenol for flow-injection-spectrophotometric determination of trace V in river water [3], Af-butyl-A -(sodium p-amino benzenesulfonate) thiourea to determine Pd in minerals and catalysts [4], benzeneacetaldehyde-4-hydroxy-oxo-aldoxime to determine Co in pharmaceuticals, biological materials and steels [5], 2,6-dichloroarsenazo for the determination of Bi in copper alloys [6], lV-undecyl-A-(sodium p-aminobenzenesulfonate)-thiourea to identify and determine Cu in alloy, liver and wheat [7], dimethoxyhydroxyphenylflurone for the determination of trace amounts of Mo in steel and pure iron [8] and 5-(6-methoxy-2-benzothiazole-azo)-8-aminoquinoline for the detection of Co in drainage sediment and Ni in A1 alloy [9] have recently been reported. 

Several examples have been reported of the preparation of 4,7-phenanthrolines from substituted 6-aminoquinolines by the Skraup and related reactions. In this way, 5-methoxy-, 5-chloro-, 3-methyl-6-methoxy-, l-methyl-, and l,2,3,4-tetrahydro-4-methyl-4,7-phenanthrolines have been synthesized while improvements have been made to the synthesis of the 3-methyl derivative. The Skraup reaction has also been applied to quaternary salts of 6-aminoquinolines. For example, 5-chloro-4-methyl-4,7-phenanthrolinium iodide (36) was obtained from the methiodide of 6-acetamido-8-chloroquinoline (35). Cyclizations starting from aminocarbostyrils have also been reported. Thus, 6-amino-1-methylcarbostyril (37) was condensed with paraldehyde in the presence of concentrated hydrochloric acid to afford 3,4-dihydro-4,8-dimethyl-3-oxo-4,7-phenanthroline (38), while under Skraup conditions, with glycerol as condensing agent, 6-amino-4-methylcarbostyril afforded 3,4-dihydro- l-methyl-3-oxo-4,7-phen-... 

These structural analogues, unlike 4-aminoquinolines offer a rather more significant derivative from the basic quinine moiety. From the structural aspect these drugs seem to be optimally substituted as evidenced by the presence of a side-chain consisting of 4 to 6-carbon atoms as well as the location of methoxy group at C-6. In general, the 8-aminoquinoline analogues are relatively more toxic than the 4-aminoquinoline counterparts. 

A repository 8-aminoquinohne derivative that would destroy the exo-ery-throcytic forms of P. vivax and P. malariae at a single dose would be useful either alone or in combination with other repository preparations [146]. Unfortunately, all attempts to date to synthesize long-acting derivatives of pamaquine, primaquine, and other 8-aminoquinolines have failed [36]. Pamaquine pamoate [148], primaquine pamoate, primaquine suraminate, and several dozen other relatively insoluble primaquine salts lacked significant repository activity in mice at doses ranging from 100 to 400 mg base/kg [36]. Further, hopes that A-[(6-methoxy-8-quinolylamino)alkyl]amides such as LVIa and b and LVIIa-c... 

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