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4053-45-6 Usage

General Description

5-(Chloromethyl)-8-quinolinol hydrochloride is a chemical compound that consists of a quinoline ring with a chloromethyl group attached at the 5th position. It is commonly used as an intermediate in the synthesis of various pharmaceuticals and other organic compounds. 5-(CHLOROMETHYL)-8-QUINOLINOL HYDROCHLORIDE has antimicrobial properties and is often used in the production of antiseptics and disinfectants. Additionally, it has been studied for its potential anti-tumor and anti-inflammatory properties. 5-(Chloromethyl)-8-quinolinol hydrochloride is also used as a chelating agent in various chemical processes, as it can form complexes with metal ions. However, it is important to handle this chemical with care, as it is a potential irritant to the skin, eyes, and respiratory system.

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 articles and documents

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.

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.

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.

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.

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.

Comparative studies of the electronic, binding and photophysical properties of a new nona-dentate hemi-cage tripodal HQ pendant trizaza-macrocycle with unfilled, half-filled and completely filled lanthanide ions

Baral, Minati,Kanungo, B. K.,Rohini

, p. 16040 - 16059 (2018)

The present paper describes the comparative studies of the electronic, photophysical and binding properties of a new C3-symmetric polydentate ligand, 1,4,7-tris-{(5-methylene-8-hydroxyquinoline)-1,4,7-triazacyclononane} (9N3Me5Ox), and its complexes with 4f0, 4f7, and 4f14 metal ions (La3+, Gd3+, and Lu3+) by experimental and theoretical methods using DFT, TDDFT, TDDFTB, ETS-NOCV, NBO and Ligand Field DFT (LFDFT). The ligand and the complexes were synthesized and characterized through elemental analysis, molar conductance, TGA, FT-IR, FT-NMR, 1H-1H COSY and ESI-mass spectrometry techniques. The spectral data and structural studies revealed the formation of nine-coordinate compounds with the general formula [Ln(9N3Me5Ox)(H2O)3], in which the nonadentate chelator acted as a trinegative hexadentate ligand coordinating to the metal ions through three sets of O,N-donors of 8-hydroxyquinoline groups and three coordinated water molecules. The molecular modeling studies suggest that the metal ion can be easily encapsulated in its central cavity forming hemi-cage complexes without altering the basic metal-ligand coordination sphere. The nature of the bonding between the lanthanide ions and 9N3Me5Ox3?, elucidated by means of the natural bond orbital (NBO), Morokuma-Ziegler energy decomposition analysis (ETS-NOCV) scheme, suggests that the Ln-L bonds are more electrostatic (~82percent) than covalent (~18percent). The covalent character of the complexes increases in the order Lu > La > Gd. The photoluminescence spectral studies of the metal complexes revealed that the observed luminescence of the compounds in the solid state and solution is of different origin. The vibrational, 1H and 13C NMR spectral data obtained from the DFT optimized structures showed good agreement with the experimental results. The excitation and emission behaviours of the ligand and the complexes were established by molecular orbital analysis of the ground state DFT geometry as well as of the excited state optimized geometry using TD-DFT and TD-DFTB orbital analysis, excitation and emission properties.

Enhanced photoluminescence and the self-assembled fibrillar nanostructure of 5-(cholesteryloxy)methyl-8-hydroxyquinoline lithium in a gel state

Kong, Sheng,Xiao, Lixin,Chen, Zhijian,Yan, Xingzhong,Qu, Bo,Wang, Shufeng,Gong, Qihuang

, p. 325 - 330 (2010)

Soluble 5-(cholesteryloxy)methyl-8-hydroxyquinoline lithium(i) (LiChQ) was synthesized through the modification of 8-hydroxyquinoline lithium (LiQ) with cholesterol, and showed about 3 times more enhanced luminescence than pristine LiQ. When increasing the concentration of LiChQ up to 1 wt% in non-protic solvents, nanoscale fibers of 30-100 nm diameter were formed through self-assembly in a super-gel state. There was a red shift in the absorption of the gel in comparison to the solution, which indicates that LiChQ tends to form a J-aggregate in the gel state. We also investigated the gelation process of LiChQ using the Lippert-Mataga equation. We suggest that LiChQ has potential applications in luminescent devices and/or as a template for nanostructured optoelectronic materials.

Synthesis and biological evaluation of selective survivin inhibitors derived from the MX-106 hydroxyquinoline scaffold

Albadari, Najah,Chen, Hao,Deng, Shanshan,Li, Wei,Miller, Duane D.,Wu, Zhongzhi,Yue, Junming,Zhang, Sicheng,Zhao, Guannan

, (2021/08/09)

The survivin (BIRC5) expression is very low in normal differentiated adult tissues, but it is one of the most widely upregulated genes in tumor cells. The overexpression of survivin in many cancer types has been positively correlated with resistance to chemotherapy, tumor metastasis, and poor patient survival. Survivin is considered to be a cancer specific biomarker and serves as a potential cancer drug target. In this report, we describe the design and syntheses of a series of novel selective survivin inhibitors based on the hydroxyquinoline scaffold from our previously reported lead compound MX-106. The best compound identified in this study is compound 12b. In vitro, 12b inhibited cancer cell proliferation with an average IC50 value of 1.4 μM, using a panel of melanoma, breast, and ovarian cancer cell lines. The metabolic stability of 12b improved over MX-106 by 1.7-fold (88 vs 51 min in human microsomes). Western blot analyses demonstrated that treatments with 12b selectively decreased survivin protein levels, but negligibly affected other closely related members in the IAP family proteins, and strongly induced cancer cell apoptosis. In vivo, compound 12b effectively inhibited melanoma tumor growth when tested using a human A375 melanoma xenograft model. Further evaluation using an aggressive, orthotopic ovarian cancer mouse model showed that 12b was highly efficacious in suppressing both primary tumor growth in ovaries and tumor metastasis to multiple peritoneal organs. Collectively, results in this study strongly suggest that the hydroxyquinoline scaffold, represented by 12b and our earlier lead compound MX-106, has abilities to selectively target survivin and is promising for further preclinical development.

Quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating Alzheimer's disease

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Paragraph 0085-0088, (2020/10/04)

The invention belongs to the technical field of medicines, and particularly relates to a quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating and/or preventing Alzheimer's disease. Specifically disclosed are a compound represented by formula (I) and a pharmaceutically acceptable salt thereof. The quinoline tryptamine heterozygote disclosed by the invention has excellent oxygen free radical scavenging capacity, a protective effect on hydrogen peroxide induced SH-SY5Y cell oxidative damage, good blood-brain barrier passive dialysis capacity, an A[beta] self-aggregation inhibiting effect and metal ion chelating capacity, and is a multi-target anti-Alzheimer disease active molecule. The compound is expected to be used as a clinical medicine for treating and/or preventing Alzheimer's disease.

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