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5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE is a chemical compound characterized by a quinoline ring with a chloromethyl group at the 5th position. It is recognized for its antimicrobial properties and is utilized as an intermediate in the synthesis of pharmaceuticals and organic compounds. 5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE also exhibits potential anti-tumor and anti-inflammatory properties, and serves as a chelating agent in chemical processes due to its ability to form complexes with metal ions. However, it requires careful handling due to its potential irritancy to the skin, eyes, and respiratory system.

4053-45-6

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4053-45-6 Usage

Uses

Used in Pharmaceutical Synthesis:
5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new medicinal compounds.
Used in Antimicrobial Applications:
In the production of antiseptics and disinfectants, 5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE is used as an active ingredient for its antimicrobial properties, helping to prevent infection and maintain hygiene.
Used in Anti-tumor and Anti-inflammatory Research:
5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE is used as a subject of study in research for its potential anti-tumor and anti-inflammatory properties, indicating its possible use in cancer and inflammatory condition treatments.
Used in Chemical Process Chelation:
As a chelating agent, 5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE is used in various chemical processes to form complexes with metal ions, which can be important for certain industrial applications and reactions.
Used in Safety and Handling Protocols:
Due to its potential irritancy, 5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE is used as a case study in the development of safety and handling protocols to protect workers in laboratories and industries from skin, eye, and respiratory irritation.

Check Digit Verification of cas no

The CAS Registry Mumber 4053-45-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,5 and 3 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4053-45:
(6*4)+(5*0)+(4*5)+(3*3)+(2*4)+(1*5)=66
66 % 10 = 6
So 4053-45-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H8ClNO.ClH/c11-6-7-3-4-9(13)10-8(7)2-1-5-12-10;/h1-5,13H,6H2;1H

4053-45-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE

1.2 Other means of identification

Product number -
Other names 5-chloromethyl-8-hydroxyquinoline hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4053-45-6 SDS

4053-45-6Synthetic route

8-quinolinol
148-24-3

8-quinolinol

formaldehyd
50-00-0

formaldehyd

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 0 - 20℃; for 4h;99%
With hydrogenchloride In water at 0 - 20℃; for 8h;98%
With hydrogenchloride In water at 0 - 20℃; for 8h; Product distribution / selectivity;98%
hydrogenchloride
7647-01-0

hydrogenchloride

8-quinolinol
148-24-3

8-quinolinol

formaldehyd
50-00-0

formaldehyd

water
7732-18-5

water

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-(hydroxymethyl)-8-hydroxyquinoline
4053-44-5

5-(hydroxymethyl)-8-hydroxyquinoline

Conditions
ConditionsYield
With ammonium hydroxide In diethyl ether99.99%
With ammonium hydroxide In water at 20℃; for 0.25h; pH=9 - 10;99%
With ammonia In water86%
With ammonium hydroxide Substitution;
methanol
67-56-1

methanol

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-methoxymethyl-8-hydroxy-7-quinoline
7545-59-7

5-methoxymethyl-8-hydroxy-7-quinoline

Conditions
ConditionsYield
With sodium hydrogencarbonate Heating;99%
Stage #1: methanol; 5-chloromethyl-8-hydroxyquinoline hydrochloride for 2h; Inert atmosphere; Reflux;
Stage #2: With ammonium hydroxide In diethyl ether; water pH=8 - 10;
88%
Stage #1: methanol; 5-chloromethyl-8-hydroxyquinoline hydrochloride Reflux;
Stage #2: With ammonium hydroxide In diethyl ether
42%
With sodium hydrogencarbonate for 2h; Reflux;
piperazine-1-carbaldehyde
7755-92-2

piperazine-1-carbaldehyde

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-(4-formylpiperazinomethyl)-8-hydroxyquinoline

5-(4-formylpiperazinomethyl)-8-hydroxyquinoline

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform for 48h;95%
2-Aminomethylthiophene
27757-85-3

2-Aminomethylthiophene

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

JLK 1535
1215290-42-8

JLK 1535

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 24h;95%
4-aminomethyl-cyclohexanecarboxylic acid
1197-17-7, 1197-18-8, 701-54-2

4-aminomethyl-cyclohexanecarboxylic acid

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

4-((bis((8-hydroxyquinolin-5-yl)methyl)amino)methyl)-cyclohexanecarboxylic acid
1215290-47-3

4-((bis((8-hydroxyquinolin-5-yl)methyl)amino)methyl)-cyclohexanecarboxylic acid

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 24h;95%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-((aminooxy)methyl)quinolin-8-ol

5-((aminooxy)methyl)quinolin-8-ol

Conditions
ConditionsYield
With hydroxylamine; sodium hydrogencarbonate In tetrahydrofuran Reflux;94%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

di-n-propylamine
142-84-7

di-n-propylamine

5-dipropylaminomethyl-quinolin-8-ol
7545-63-3

5-dipropylaminomethyl-quinolin-8-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.416667h;93%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

diphenylamine
122-39-4

diphenylamine

5-((diphenylamino)methyl)-quinolin-8-ol
1065474-08-9

5-((diphenylamino)methyl)-quinolin-8-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.416667h;91%
With triethylamine In dichloromethane at 20℃;
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

5-(N'-boc-piperazinomethyl)-8-hydroxyquinoline

5-(N'-boc-piperazinomethyl)-8-hydroxyquinoline

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃;91%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

N-Benzoylpiperazine
13754-38-6

N-Benzoylpiperazine

5-(4-benzoylpiperazin-1-ylmethyl)-quinolin-8-ol
1103590-34-6

5-(4-benzoylpiperazin-1-ylmethyl)-quinolin-8-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.416667h;90%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-azidomethyl-8-hydroxyquinoline
1005143-73-6

5-azidomethyl-8-hydroxyquinoline

Conditions
ConditionsYield
With sodium azide In acetone for 20h; Heating;90%
With sodium azide In acetone for 24h; Reflux;85%
With sodium azide In acetone for 20h; Reflux; Inert atmosphere;77%
TETRAHYDROFURFURYLAMINE
4795-29-3

TETRAHYDROFURFURYLAMINE

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5,5'-((tetrahydrofuran-2-yl)methylazanediyl)bis(methylene)-diquinolin-8-ol
1215290-43-9

5,5'-((tetrahydrofuran-2-yl)methylazanediyl)bis(methylene)-diquinolin-8-ol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 24h;90%
p-Trifluoromethylbenzylamine
3300-51-4

p-Trifluoromethylbenzylamine

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5,5'-(4-(trifluoromethoxy)benzylazanediyl)bis(methylene)diquinolin-8-ol
1215290-40-6

5,5'-(4-(trifluoromethoxy)benzylazanediyl)bis(methylene)diquinolin-8-ol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 24h;90%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

benzyl alcohol
100-51-6

benzyl alcohol

5-benzyloxymethyl-8-hydroxy-quinoline hydrochloride
1052523-62-2

5-benzyloxymethyl-8-hydroxy-quinoline hydrochloride

Conditions
ConditionsYield
at 90℃; for 2h; Inert atmosphere;90%
at 110℃;
2-[(2,2-dichloroethyl)(4-(4-nitrophenoxy)benzyl)amino]ethanol
1327167-54-3

2-[(2,2-dichloroethyl)(4-(4-nitrophenoxy)benzyl)amino]ethanol

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-((2-((2,2-dichloroethyl)(4-(4-nitrophenoxy)benzyl)amino)ethoxy)methyl)quinolin-8-ol
1327167-53-2

5-((2-((2,2-dichloroethyl)(4-(4-nitrophenoxy)benzyl)amino)ethoxy)methyl)quinolin-8-ol

Conditions
ConditionsYield
With potassium carbonate In acetone for 8h; Reflux;90%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-(hydrazinylmethyl)quinolin-8-ol

5-(hydrazinylmethyl)quinolin-8-ol

Conditions
ConditionsYield
With sodium hydrogencarbonate; hydrazine In tetrahydrofuran Reflux;90%
morpholine
110-91-8

morpholine

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-(morpholin-4-ylmethyl)-quinolin-8-ol

5-(morpholin-4-ylmethyl)-quinolin-8-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.416667h;88%
In chloroform at 5 - 20℃;59%
potassium cyanide

potassium cyanide

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

2-(8-hydroxyquinolin-5-yl)acetonitrile
57434-83-0

2-(8-hydroxyquinolin-5-yl)acetonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere; Molecular sieve;88%
With molecular sieve 4Å In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere;88%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

sulfanilamide
63-74-1

sulfanilamide

4-{[(8-hydroxyquinolin-5-yl)methyl]amino}benzenesulfonamide
1259419-39-0

4-{[(8-hydroxyquinolin-5-yl)methyl]amino}benzenesulfonamide

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; Reflux;87.8%
With triethylamine In acetonitrile Activation energy; Heating;
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

1-prop-2-ynylpiperazine
52070-67-4

1-prop-2-ynylpiperazine

5-((4-propargylpiperazin-1-yl)methyl)-8-hydroxyquinol

5-((4-propargylpiperazin-1-yl)methyl)-8-hydroxyquinol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 0 - 20℃; for 24h;86%
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

2-aminomethyl-1-methyl-1H-pyrrole
69807-81-4

2-aminomethyl-1-methyl-1H-pyrrole

5,5'-((1-methyl-1H-pyrrol-2-yl)methylazanediyl)bis-(methylene)diquinolin-8-ol
1215290-44-0

5,5'-((1-methyl-1H-pyrrol-2-yl)methylazanediyl)bis-(methylene)diquinolin-8-ol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 24h;86%
ethanol
64-17-5

ethanol

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-Ethoxymethyl-8-hydroxyquinolin-1-ium chloride

5-Ethoxymethyl-8-hydroxyquinolin-1-ium chloride

Conditions
ConditionsYield
for 3h; Reflux;86%
at 90℃; for 2h;
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

4-(4-chloranylphenyl)-2,6-dimethyl-3,5-bis-(1-oxidanylideneethyl)-1,4-dihydropyridine
173171-93-2

4-(4-chloranylphenyl)-2,6-dimethyl-3,5-bis-(1-oxidanylideneethyl)-1,4-dihydropyridine

1,1'-(4-(4-chlorophenyl)-1-((8-hydroxyquinolin-5-yl)methyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-diyl)diethanone

1,1'-(4-(4-chlorophenyl)-1-((8-hydroxyquinolin-5-yl)methyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-diyl)diethanone

Conditions
ConditionsYield
With potassium carbonate; triethylamine In N,N-dimethyl-formamide at 80℃; for 12h;86%
diaminodecane
646-25-3

diaminodecane

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

C50H52N6O4
81409-97-4

C50H52N6O4

Conditions
ConditionsYield
With triethylamine In toluene for 2.5h; Heating;85%
Methyl 2,2-dimethyl-3-hydroxypropionate
14002-80-3

Methyl 2,2-dimethyl-3-hydroxypropionate

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-(2-carbomethoxy-2-methyl)propyloxymethyl-8-hydroxy-7-quinoline
1245934-94-4

5-(2-carbomethoxy-2-methyl)propyloxymethyl-8-hydroxy-7-quinoline

Conditions
ConditionsYield
Stage #1: Methyl 2,2-dimethyl-3-hydroxypropionate; 5-chloromethyl-8-hydroxyquinoline hydrochloride for 2h; Inert atmosphere; Reflux;
Stage #2: With ammonium hydroxide In diethyl ether; water pH=8 - 10;
85%
propan-1-ol
71-23-8

propan-1-ol

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-n-Propoxymethyl-8-hydroxyquinolin-1-ium chloride

5-n-Propoxymethyl-8-hydroxyquinolin-1-ium chloride

Conditions
ConditionsYield
for 3h; Reflux;85%
at 90℃; for 2h;
5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

5-{[(2-hydroxyethyl)sulflanyl]methyl}quinolin-8-ol

5-{[(2-hydroxyethyl)sulflanyl]methyl}quinolin-8-ol

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran for 8h; Reflux;85%
N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

5-dimethylaminomethyl-quinolin-8-ol
7545-62-2

5-dimethylaminomethyl-quinolin-8-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.416667h;84%
potassium cyanide
151-50-8

potassium cyanide

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

2-(8-hydroxyquinolin-5-yl)acetonitrile
57434-83-0

2-(8-hydroxyquinolin-5-yl)acetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 95℃; for 1h;84%

4053-45-6Relevant academic research and scientific papers

Facile route fabrication of nickel based mesoporous carbons with high catalytic performance towards 4-nitrophenol reduction

Yang, Ying,Ren, Yang,Sun, Chengjun,Hao, Shijie

, p. 2273 - 2280 (2014)

Novel nickel based mesoporous carbons are firstly in situ fabricated via pyrolysis of CTAB-chitosan-nickel supramolecular aggregates, which are pre-constructed by CTAB-directed self-assembly of 8-quinolinol modified chitosan and nickel acetate under basic conditions. This facile route fabrication method renders smart and homogeneously dispersed Ni nanoparticles (NPs) on the mesoporous carbonaceous framework without using any stabilizer and additional reductant, verified by high-energy X-ray diffraction, TEM, X-ray absorption fine structure, N2 adsorption/desorption and Raman spectroscopy. Moreover, it is found that the morphology of Ni NPs, the textural property of carbonaceous supports, and the corresponding catalytic performance towards 4-nitrophenol reduction vary with the pyrolysis temperature. It is suggested that the nickel based mesoporous carbon pyrolyzed at 750 °C (Ni/MC-750) simultaneously possessing uniform spherical Ni NPs (24.5 nm) and bottle-neck mesopores exhibits the largest activity factor of 20.9 s-1 g -1 of any nickel catalysts. the Partner Organisations 2014.

Rational design of 5-((1H-imidazol-1-yl)methyl)quinolin-8-ol derivatives as novel bromodomain-containing protein 4 inhibitors

Xing, Jing,Zhang, Rukang,Jiang, Xiangrui,Hu, Tianwen,Wang, Xinjun,Qiao, Gang,Wang, Junjian,Yang, Fengling,Luo, Xiaomin,Chen, Kaixian,Shen, Jingshan,Luo, Cheng,Jiang, Hualiang,Zheng, Mingyue

, p. 281 - 294 (2019)

Bromodomain-containing protein 4 (BRD4), an epigenetic reader of acetyl lysine, has emerged as a promising therapeutic target for many diseases including cancer, inflammation and heart failure. Our previous study reported that nitroxoline, an FDA approved antibiotic, showed potential BRD4 inhibitory activity and antiproliferation activity against leukemia cell lines. In this study, we further explored the structure-activity relationship (SAR) around nitroxoline and employed our previously developed machine learning based activity scoring function BRD4LGR for further analysis. To improve the cellular level activity, physico-chemical properties were optimized using computational approaches. Then the candidates were tested for their ADME/T profiles. Finally, based on this rational hit-to-lead optimization strategy, 3 drug-like BRD4 inhibitors were obtained, with different profiles on cell line selectivity for multiple myeloma, leukemia and triple negative breast cancer. Further mechanism study showed these compounds could down-regulate c-Myc to inhibit cancer cell growth. This work illustrates the application of multiple computer-aided drug design techniques in a hit-to-lead optimization scenario, and provides novel potent BRD4 inhibitors with different phenotype propensities for future cancer treatment.

Experimental investigation on the corrosion inhibition of carbon steel by 5-(chloromethyl)-8-quinolinol hydrochloride in hydrochloric acid solution

El Faydy,Galai,El Assyry,Tazouti,Touir,Lakhrissi,Ebn Touhami,Zarrouk

, p. 396 - 404 (2016)

5-(chloromethyl)-8-quinolinol hydrochloride (Cl-QH) was synthesized and characterized. Thus, its inhibition effect on XC38 steel corrosion in 1 M HCl medium was investigated using weight loss and electrochemical measurements. Polarization measurements indicated that, the studied compound acts as a mixed type inhibitor, the inhibition efficiency depends on its concentration and reaches 97% at 10- 3 M. Electrochemical impedance spectroscopy showed that the Cl-QH acts by the formation of a protective film at the metallic surface. The adsorption of the studied compound followed the Langmuir isotherm. So, scanning electronic microscopy (SEM) confirms the performance of Cl-QH against corrosion. In addition, quantum chemical calculations using DFT at the B3LYP/6-31G?level of theory was further used to calculate and discussed some electronic properties of the studied molecule. The theoretical and experimental results are in good agreement.

Synthesis and photophysics of novel 8-hydroxyquinoline aluminum metal dye with hole transfer groups

Wang, Xiaoju,Feng, Liheng,Chen, Zhaobin

, p. 1433 - 1437 (2008)

A novel luminescent dye metal complex, (CZHQ)3Al, with 8-hydroxyquinoline aluminum and hole-transporting carbazole units was designed and synthesized. The (CZHQ)3Al optical properties were carefully investigated by UV-vis absorption and fluorescence spectra in diluent solution. The results showed that the luminescent quantum yield of (CZHQ)3Al was 0.62 in DMSO and it emitted red-light with the band gap of 2.89 eV estimated from the onset absorption. In addition, the light-emission of (CZHQ)3Al can be quenched by electron acceptor (dimethylterephalate), where the process followed the Stern-Volmer equation. However, the fluorescent intensities of (CZHQ)3Al were slowly increased with the addition of electron donor (N,N-dimethylaniline). Furthermore, the molecular interactions of (CZHQ)3Al with fullerene (C60) and carbon nanotubes (CNTs) were also respectively investigated, which indicated the metal dye can be used as new fluorescent probe.

Coordination polymers of N, N'-di-(8-Hydroxyquinolinolyl- 5-methyl)-N, N-diethyl-1, 3-propane diamine (QEPD)

Patel, Asha D.,Patel, Rignesh S.,Patel, Ganpat R.

, p. 1023 - 1028 (2010)

Coordination polymers containing a novel bis(oxine) bidentate ligand, namely N,N'-di(8-hydroxyquinolinolyl-5-methyl)-N,N'-diethyl-1,3- propane diamine (QEPD) have been prepared with the metal ions Zn(II), Cu(II), Ni(II), Co(II) and Mn(II). The novel bis-(bidentate) ligand was synthesized by condensation of 5-chloromethyl-8-hydroxyquinoline hydrochloride with N,N'-diethyl-1,2- propane diamine in the presence of a base catalyses. All of these coordination polymers and the parent ligand were characterized by elemental analyses, IR spectral and diffuse reflectance spectral studies. The thermal stability and number- average molecular weights (Mn) of all of the coordination polymers were determined by thermogravimetric analyses and non-aqueous conductometric titrations, respectively. In addition, all of the coordination polymers have been characterized by their magnetic susceptibilities.

Design, Synthesis, and Evaluation of Orally Bioavailable Quinoline-Indole Derivatives as Innovative Multitarget-Directed Ligands: Promotion of Cell Proliferation in the Adult Murine Hippocampus for the Treatment of Alzheimer's Disease

Wang, Zhiren,Hu, Jinhui,Yang, Xiaoping,Feng, Xing,Li, Xingshu,Huang, Ling,Chan, Albert S. C.

, p. 1871 - 1894 (2018)

A novel series of quinoline-indole derivatives were synthesized and evaluated as multitarget-directed ligands for the treatment of Alzheimer's disease (AD). Biological evaluation revealed that the derivatives had multifunctional profiles including antioxidant effects, blood-brain barrier (BBB) penetration, biometal chelation, Aβ aggregation modulation, neurotrophic and neuroprotective properties. Moreover, several representative target derivatives demonstrated hippocampal cell proliferation in living adult mice by intracerebroventricular (icv) injection or oral administration. Further drug-like property analysis demonstrated that the optimized compound, 8d (WI-1758), had liver microsomal metabolic stability, was well tolerated (>2000 mg/kg), and had a rational pharmacokinetic profile, as well as an oral bioavailability of 14.1% and a positive log BB (-0.19) to cross the BBB in vivo. Pharmacodynamics studies demonstrated that chronic oral administration of 8d·HCl substantially ameliorated the cognitive and spatial memory deficits in APP/PS1 AD mice and noticeably reduced overall cerebral β-amyloid deposits.

Synthesis and characterization of novel Cu (II) and Zn (II) complexes of 5-{[(2-Hydroxyethyl) sulfanyl] methyl}-8-hydroxyquinoline as effective acid corrosion inhibitor by experimental and computational testings

Abousalem, Ashraf S.,Benhiba, F.,Ebn Touhami, M.,Galai, M.,Jama, C.,Lai, Chin-Hung,Lakhrissi, B.,Ouakki, M.,Rbaa, M.,Warad, I.,Zarrouk, A.

, (2020)

Two new complexes were synthesized, characterized and tested as inhibitors for mild steel corrosion in 1.0 M HCl. The anticorrosive effect has been studied using the potentiodynamic polarization (PDP) and impedance spectroscopy (EIS). The inhibitory efficiency increases with increasing concentration to reach 96.0percent for Q-Cu and 94.6percent for Q-Zn at 10?3 M. The two inhibitors are mixed type and follows the Langmuir isotherm adsorption. The surface of the mild steel has been examined by SEM/EDS and the corrosive solution by ICP-OES. DFT calculations and molecular dynamic simulation (MD) show a good correlation with the experimental results for both complexes.

Spectroscopic, photophysical, solution thermodynamics and computational study of europium and terbium complexes with a flexible quinolinol-based symmetric tripodal chelator

Akbar, Rifat,Baral, Minati,Kanungo, B. K.

, (2021)

Coordination behaviour and photonic properties of a flexible tripodal multidentate ligand, 5,5′,5′'-(Cyclohexane-1,3,5-triyltris(oxy))tris(methylene)triquinolin-8-ol (CYTOM5OX), with Eu and Tb ions were explored through potentiometric, UV-visible and fluorescence spectrophotometric methods. The interaction of tripod towards the lanthanides has been examined for thermodynamic equilibrium, photophysical behavior, and time-resolved luminescence measurements. Besides, a theoretically empirical method followed by quantum mechanical treatment of these chelates has also been summarized. A noticeable change in the electronic spectra of these complexes disclose CYTOM5OX as a pH-sensitive optical sensor for lanthanides detection; also, a strong green fluorescence allows simultaneous sensing in the visible region in a competitive medium. The intense fluorescence intermittently gets quenched under acidic and basic conditions due to photoinduced intramolecular electron transfer from the excited 8-hydroxyquinoline (8-HQ) moiety to the metal ion. The thermodynamically stable Ln3+ complexes in aqueous solution show stability constants in the range log β110 = 33–35 and pLn3+ in the range of 21–22. The hydration number that was predicted by the coordination scan was substantiated by lifetime measurements reveal presence of coordinated water molecules in Eu(CYTOM5OX) and Tb(CYTOM5OX) complexes. Theoretical spectra were also calculated by ZINDO/s methodology at single excitations (CIS) level on PM7 as sparkle energy-minimized geometries.

Design and Synthesis of Nanosensor Based on CdSe Quantum Dots Functionalized with 8-Hydroxyquinoline: a Fluorescent Sensor for Detection of Al3+ in Aqueous Solution

Eftekhari-Sis, Bagher,Samadneshan, Khadijeh,Vahdati-Khajeh, Saleh

, p. 767 - 774 (2018)

A novel nanosensor based on CdSe quantum dots (QDs) capped with 8-hydroxyqunoline (HQ) was developed for Al3+ ions determination in aqueous solutions. The method is based on the fluorescence enhancement of the HQ functionalized QDs in the presence of Al3+ ions, due to the strong interaction between Al3+ and HQ. Prepared nanosensor exhibited an acceptable selectivity and sensitivity for Al3+ ions in the presence of other metal ions. Plot of Log(I/I0) against Log[Al3+] shows a good linearity in the range of 0.02–3.0?mM, and the method could be used for detection of Al3+ ions concentration in aqueous solutions.

Sample synthesis, characterization, experimental and theoretical study of the inhibitory power of new 8-hydroxyquinoline derivatives for mild steel in 1.0 M HCl

Abousalem, Ashraf S.,Benhiba, F.,Galai, M.,Lakhrissi, B.,Oudda, H.,Rbaa, M.,Rouifi, Z.,Warad, I.,Zarrouk, A.

, (2020)

Some new compounds which are derived from 8-hydroxyquinoline were both prepared and characterized by IR, NMR spectroscopy and elemental analysis. After the successful synthesis, we tested these products as corrosion inhibitors of mild steel (MS) in 1.0 M HCl at 298 K ± 1. The anticorrosive property was achieved by electrochemical and theoretical methods such as potentiodynamic polarization (PDP), the spectroscopy impedance (EIS), density functional theory (DFT) calculations and the Monte Carlo simulation (MC). The experimental and theoretical results obtained show that these products have an excellent anticorrosive property for the MS. The thermodynamic parameters show that all the compounds adsorb to the metal surface by chemical bonds according to the Langmuir adsorption isotherm. The surface morphology was investigated using scanning electron spectroscopy (SEM) coupled with energy dispersive spectroscopy (EDS) and the FT-IR analysis. The gravimetric solutions after 6 h of immersion were analyzed by the UV–Visible spectrometry.

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