8-Aminoquinoline | Quinolines

8-Aminoquinoline is a quinoline derivative with antimalarial activity, with representative drugs such as Primaquine, widely used in the treatment of malaria and parasitic infections.

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Quality Control of 8-Aminoquinoline Purity: 97% SDS Specification

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Product Citations Show More

Ruthenium (II)–arene complexes with chelating quinoline ligands as anti-amyloid agents

Meiss, Cade J ; Bothwell, Paige J ; Webb, Michael I ;

DOI: 10.1139/cjc-2021-0180 Can. J. Chem.,2022,100(1):18-24.

Abstract: Recent recognition of the soluble form of the amyloid-beta (Ab) peptide as a neurotoxic agent in Alzheimer’sdis ease (AD) has spurred the development of agents to target this species. Because Ab is known to chelate metal ions in solu tion, metal-based therapeutics are uniquely suited to exploit this affinity, where coordination to Ab has been shown to impact the neurotoxicity of the peptide. Ruthenium(II)–arene complexes are unique candidates for evaluation, as one face ofthemoleculeisblockedbythehydrophobicarenering,whilecoordinationtotheAb peptide can occur on the other side of the molecule. We have prepared and evaluated two Ru(II)–arene complexes with chelating quinoline-based ligands, Ru1 and Ru2, for their respective anti-amyloid abilities. Although both complexes decreased the aggregation of soluble Ab, Ru1 displayed promise in disrupting formed aggregates of the peptide. These findings represent an exciting new avenue for therapeutic development in AD, where both sides of the aggregation equilibrium are affected.

Keywords: Alzheimer’s disease ; amyloid-beta ; ruthenium(II) therapeutics ; peptide aggregation

Purchased from AmBeed: 578-66-5

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;

DOI: 10.1021/acs.joc.1c01431 PubMed ID: 34983185 JOC,2022,87(2):910-919.

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Purchased from AmBeed: 607-35-2 ; 578-66-5 ; 613-50-3 ; 100-19-6 ; 579-71-5 ; 3034-94-4 ; 5683-43-2 ; 99-92-3 ; 13534-97-9 ; 5676-60-8 ; 5470-18-8 ; 619-45-4 ; 553-26-4 ; 580-15-4 ; 611-34-7 ; 619-72-7 ; 100-13-0 ; 540-37-4 ; 1849-25-8 ; 4487-59-6 ; 555-16-8 ; 6298-19-7 ; 556-08-1 ; 953-26-4 ; 54060-30-9 ; 62-23-7 ; 607-34-1 ; 3867-18-3 ; 873-74-5 ; 3544-24-9 ; 94-52-0 ; 1520-21-4 ; 5470-34-8 ; 619-50-1 ; 586-39-0 ; 934-22-5 ; 402-54-0 ; 15411-43-5 ; 455-14-1 ; 17763-80-3 ; 3085-54-9 ; 1942-30-9 ; 1694-20-8 ; 6305-66-4 ; 41656-75-1 ; 6393-17-5 ; 4309-66-4

Product Details of 8-Aminoquinoline

CAS No. :	578-66-5
Formula :	C₉H₈N₂
M.W :	144.17
SMILES Code :	NC1=C2N=CC=CC2=CC=C1
MDL No. :	MFCD00006809
InChI Key :	WREVVZMUNPAPOV-UHFFFAOYSA-N
Pubchem ID :	11359

Safety of 8-Aminoquinoline

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P305+P351+P338

Application In Synthesis of 8-Aminoquinoline

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 578-66-5 ]

[ 578-66-5 ] Synthesis Path-Downstream 1~35

1
[ 578-66-5 ]
[ 31736-73-9 ]
[ 97802-07-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1985,p. 705 - 710.
[2]Patent: US2018/212158,2018,A1 .Location in patent: Paragraph 0550.

2
[ 578-66-5 ]
[ 22744-12-3 ]
[ 1350651-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 12h;	Methyl 4-(2-oxo-2-(quinolin-8-ylamino)ethyI)benzoate, 67.; Compound 57 (300 mg, 1.26 rrnriol) was heated at 100 C for 1 h. The reaction mixture was dissolved in methanol and passed through a short silica gel column. To the crude 66 (240 mg,1.24 mmol) in CH2CI2 (20 mL) was added 8-aminoquinoline (196 mg, 1.36 mmol) and EDC(261 mg, 1.36 mmol) and the mixture was allowed to stir at rt for 12 h. Water was added and the mixture was worked up with CH2CI2. The organic layer was dried with anhyd Na2SC" and the solvent removed under reduced pressure. The residue was purified by flash column (silica gel 230-400 mesh, 30% ethyl acetate in hexanes as the eluent) to yield 67 as a colorless crystalline solid (342 mg, 85%). NMR (400 MHz, CDCI3): 0 = 3.91 (s, 3H), 3.96 (s, 2H), 7.43-7.46 (m, 1H), 7.51-7.53 (m, 4H), 8.06 (d, 2H, J = 8.4 Hz), 8.18-8.20 (m, 1H), 8.72-8.76 (m, 2H), 10.00 (s, 1H). I3C NMR (75 MHz, CDCI3): delta = 45.4, 52.4, 116.9, 121.9, 122.1, 127.6, 128.1, 129.4, 129.8, 130.4, 134.4, 136.8, 138.4, 140.2, 148.4, 167.1, 168.8. LRMS Calcd for C\|9Hi6 203: 321.11 Found: 321.07. l)

References: [1]Patent: WO2011/146855,2011,A1 .Location in patent: Page/Page column 89-90.

3
[ 578-66-5 ]
[ 6557-86-4 ]
[ 1385719-16-3 ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13606 - 13610.
Angew. Chem.,2013,vol. 125,p. 13851 - 13855,5.
[2]Organic Letters,2022,vol. 24,p. 536 - 541.

4
[ 578-66-5 ]
[ 89694-46-2 ]
[ 1644565-60-5 ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 8761 - 8770.

5
[ 578-66-5 ]
[ 41602-56-6 ]
C₁₈H₁₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.2%	In methanol; for 3h;Reflux; Inert atmosphere;	Quinolin-8-amine (0.36 g, 2.5 mmol) and compound 2 (0.41 g, 2.5 mmol) were mixed in dry methanol (25 ml). The mixture was refluxed for 3 h under N2. Then the methanol was evaporated and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1:3) to give sensor 1 in 65.2 % yield as green-brown solid. 1H NMR (400 MHz, DMSO-d6): delta 3.02 (s, 6H, CH3), 5.96-6.37 (m, 3H, Ar-H), 7.30-8.82 (m, 6H), 9.12 (s, 1H, CH=N), 13.97 (s, 1H, OH); ESI-MS: 292.1417 (M+H+); Anal. calcd. for C18H17N3O: C, 74.18; H, 5.89; N, 14.39; O, 5.54 (see Scheme 1).

References: [1]Journal of Photochemistry and Photobiology B: Biology,2014,vol. 138,p. 75 - 79.

6
[ 578-66-5 ]
[ 459-04-1 ]
2-(4-fluorophenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
197 mg	With triethylamine; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	General procedure: A dry flask containing the corresponding carboxylic acid (1 mmol) and SOCl2 (0.6 mL) was heated at 80 C for 4 h under a nitrogen atmosphere. After the reaction period, the reaction mixture was concentrated under reduced pressure to remove the volatiles and then, the resultant crude reaction mixture was diluted with anhydrous DCM (2 mL). The DCM solution of corresponding acid chloride was slowly added to another RB flask containing the corresponding amine (1 mmol), Et3N (111 mg, 1.1mmol) and DCM (4 mL) under a nitrogen atmosphere. The resulting mixture was stirred at rt for 12 h. After this period, the reaction mixture was diluted with dichloromethane and washed with water and saturated aqueous NaHCO3 solution (twice). The combined organic layers were dried over anhydrous Na2SO4 and then, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography (neutral alumina (EtOAc/hexanes=25:75) furnished the corresponding products 1f-j.

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 13602 - 13605.
[2]Tetrahedron,2016,vol. 72,p. 5886 - 5897.

7
[ 578-66-5 ]
[ 28697-11-2 ]
(-)-(S)-benzyl 2-(quinolin-8-ylcarbamoyl)piperidine-1-carboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 956 - 968.

8
[ 40915-37-5 ]
[ 578-66-5 ]
[ 1428858-71-2 ]

References: [1]Chemistry - An Asian Journal,2016,vol. 11,p. 380 - 384.

9
[ 40915-37-5 ]
[ 578-66-5 ]
7,8-dipropyl-1-(quinolin-8-yl)-4,5-dihydro-2H-pyrano[3,2-c]pyridin-2(1H)-one [ No CAS ]

References: [1]Chemistry - An Asian Journal,2016,vol. 11,p. 380 - 384.

10
[ 578-66-5 ]
[ 141-75-3 ]
[ 103962-05-6 ]
[ 1588490-21-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; silver carbonate; In o-xylene;Inert atmosphere;	General procedure: A mixture of 8-aminoquinoline (0.4mmol), an appropriate carbonyl chloride (0.4mmol), an appropriate aryl iodide (0.16-0.24mmol, 4-6 equiv), Pd(OAc)2 (10mol %) and Ag2CO3 (0.6-0.8mmol, 1.5-2 equiv) was heated in o-xylene (2mL) at 110 C for an appropriate reaction period (12-36 h). Then, reaction mixture was cooled to rt and the solvent evaporated in vacuo to give the crude product, which was purified by chromatography to give the corresponding C-H arylated products (see the respective Tables 1-4/Scheme 2 for the specific entries and reaction conditions).

References: [1]Tetrahedron,2016,vol. 72,p. 5853 - 5863.

11
[ 578-66-5 ]
[ 28697-11-2 ]
C₂₄H₂₄N₂O₃ [ No CAS ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 11646 - 11655.

12
[ 578-66-5 ]
[ 19156-54-8 ]
C₂₄H₁₈N₂OS [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 1764 - 1767.

13
[ 578-66-5 ]
[ 19156-54-8 ]
C₁₈H₁₆N₂OS [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 1764 - 1767.

14
[ 578-66-5 ]
[ 1798-06-7 ]
C₁₇H₁₃IN₂O [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 5106 - 5109.
[2]European Journal of Organic Chemistry,2018,vol. 2018,p. 6167 - 6175.
[3]Journal of Organic Chemistry,2019,vol. 84,p. 13194 - 13202.
[4]Organic Letters,2020,vol. 22,p. 7556 - 7561.
[5]Chemical Communications,2021,vol. 57,p. 6241 - 6244.

15
[ 578-66-5 ]
[ 13612-34-5 ]
2-(2,5-dimethylphenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]

References: [1]Chemistry - A European Journal,2017,vol. 23,p. 17659 - 17662.

16
[ 578-66-5 ]
[ 13612-34-5 ]
(E)-methyl 3-(3,6-dimethyl-2-(2-oxo-2-(quinolin-8-ylamino)ethyl)phenyl)acrylate [ No CAS ]

References: [1]Chemistry - A European Journal,2017,vol. 23,p. 17659 - 17662.

17
[ 578-66-5 ]
[ 51997-51-4 ]
1-((9H-carbazol-4-yl)oxy)-3-(quinolin-8-ylamino)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In methanol; at 50℃; for 16h;	The intermediate product a (300 mg, 1 . 26mmol) for 15 ml methanol dissolved, add 8 - amino quinoline (222 mg, 1 . 5mmol), heating to 50 C to the raw reaction is complete, the reaction time is about 16h. Evaporate the solvent under reduced pressure, it is crude, purification of the crude product by column chromatography (petroleum ether: ethyl acetate=10:3), a yellow solid P - Z - 001 (298 mg, 62%). 1
62%	In methanol; at 50℃; for 16h;	A solution of <strong>[51997-51-4]4-(oxiran-2-ylmethoxy)-9H-carbazole</strong> (300mg, 1.26 mmol) in 15 mL of MeOH was added to the 8-aminoquinoline (222 mg, 1.5 mmol). The mixture washeated at 50 C for 16 h. The solution was evaporated invacuo. The crude products was purified by column chromatographyover silica gel (10:3, petroleum ether/ethylacetate) to afford PZ001 as a faint yellow solid (298 mg,62%). 1H NMR (400 MHz, DMSO) delta11.26 (s, 1H), 8.73 (d,J = 3.7 Hz, 1H), 8.28 (d, J = 7.8 Hz, 1H), 8.20 (d, J = 8.1Hz, 1H), 7.49 (dd, J = 8.2, 4.2 Hz, 1H), 7.44 (d, J = 8.1 Hz,1H), 7.30 (dq, J = 16.0, 8.0, 7.5 Hz, 3H), 7.12 (t, J = 7.4Hz, 1H), 7.06 (dd, J = 8.0, 4.0 Hz, 2H), 6.76 (d, J = 7.7 Hz,1H), 6.70 (d, J = 7.9 Hz, 1H), 5.56 (s, 1H), 4.43-4.34 (m,1H), 4.26 (d, J = 5.1 Hz, 2H), 3.68 (d, J = 10.2 Hz, 1H),3.48 (dd, J = 12.8, 7.0 Hz, 1H).13C NMR (100MHz,DMSO) delta155.31, 147.42, 145.11, 141.60, 139.40, 138.03,136.45, 128.78, 128.22, 126.95, 125.03, 122.99, 122.20,122.17, 119.06, 113.85, 112.05, 110.84, 104.90, 104.45,100.95, 70.79, 68.05, 55.38, 46.57.HRMS calcd. for C24H21N3O2 [M+H]+: 384.1713. Found: 384.1707. HPLCpurity: 98.4%.

References: [1]Patent: CN106749184,2017,A .Location in patent: Paragraph 0020; 0021; 0022.
[2]Medicinal Chemistry Research,2018,vol. 27,p. 777 - 784.

18
[ 578-66-5 ]
[ 30448-16-9 ]
C₁₉H₁₅N₃O [ No CAS ]