73568-44-2

Usage

Structure

Derivative of 8-hydroxyquinoline
Chloro substituent at the 6-position
Formyl group at the 3-position

Usage

Synthesis of pharmaceuticals and agrochemicals

Properties

Potential antioxidant
Potential anti-inflammatory agent
Potential antimicrobial agent

Applications

Research and development in pharmaceuticals
Investigation for disease treatment
Functional material in organic electronics

InChI:InChI=1/C10H6ClNO2/c11-8-1-2-9-6(4-8)3-7(5-13)10(14)12-9/h1-5H,(H,12,14)

Upstream product

• 78708-19-7 (E)-N-(4-Chloro-phenyl)-2-formyl-3-hydroxy-acrylamide 
• 106-47-8 4-chloro-aniline 
• 78708-06-2 (E)-N-(4-Chloro-phenyl)-3-dimethylamino-2-formyl-acrylamide 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 73568-41-9 2,6-dichloroquinoline-3-carbaldehyde 

Downstream Products

• 1420065-43-5 C₂₆H₂₂ClN₃O₂S 

Relevant academic research and scientific papers

Synthesis, photophysical properties and theoretical studies of new bis-quinolin curcuminoid BF2-complexes and their decomplexed derivatives

This paper presents the synthesis and characterization of two series of new bis-quinolin curcuminoid BF2-complexes 11 and their respective decomplexed bis-quinolin curcuminoid derivatives 12, in an attempt to understand their optical properties. The synthesized compounds showed interesting fluorescent characteristics in both solution and in solid-state. The characteristic of the electronic transitions involved in these systems were measured via Uv-vis spectroscopy and fluorescence spectroscopy. Results revealed that the absorption and emission bands are dependent of the structure of compounds 11 and 12 but also of the type of substituent, even showing a push-pull behavior in those derivatives substituted with methyl group. These findings were also confirmed through computational calculations at DFT level via simulations of the Uv-vis spectra and determining the topology of the border orbitals responsible for light absorption.

Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH(Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.

Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones

Fifteen 2-quinolone thiosemicarbazone derivatives of which eleven were new, were synthesized at room temperature. The key intermediate was the quinolone carbaldehyde, from which thiosemicarbazones were formed by the reaction of thiosemicarbazides with the aldehyde moiety. The structures of the synthesized compounds were elucidated by 1D and 2D-NMR spectroscopy and mass spectrometry. The synthesized compounds showed antibacterial activity with MBCs in the range 0.80 to 36.49 mM against Staphylococcus aureus, Staphylococcus aureus Rosenbach (MRSA), Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli and Salmonella typhimurium. The best activity was seen when a larger halogen such as chlorine and bromine were substituted at C-6 on the quinolone scaffold and when a planar phenyl group was present on the thiosemicarbazone moiety. Activity was reduced when a smaller fluorine atom was present at C-6 or when a methyl group was attached to the thiosemicarbazone. This group of compounds showed a high negative binding affinity, which suggested promising antimcrobial activity. The 6-chloro derivative with a phenyl group on the thiosemicarbazone had the greatest negative binding affinity.

Microwave-assisted synthesis of diversely substituted quinoline-based dihydropyridopyrimidine and dihydropyrazolopyridine hybrids

An efficient, catalyst-free, and one-pot three-component procedure for the synthesis of novel and nitrogen rich dihydropyrido[2, 3-d]pyrimidines and dihydro-1H-pyrazolo[3, 4-b]pyridines bearing a quinoline pharmacophore fragment is provided. Reactions proceeded in DMF under microwave irradiation of three-component mixtures of formyl-quinoline derivatives, primary heterocyclic amines and cyclic 1, 3-diketones. Interestingly, when conventional heating at reflux was used for the starting 5-amino-1-phenylpyrazole, the corresponding aromatized pyrazolopyridines were obtained as the main products. Single crystal X-ray analysis confirmed unequivocally the structure of both the dihydro- and aromatized products.

A Schmidt rearrangement-mediated synthesis of novel tetrahydro-benzo[1,4]diazepin-5-ones as potential anticancer and antiprotozoal agents

Novel tetrahydro-5H-benzo[e][1,4]diazepin-5-ones, several of them, containing the quinoline pharmacophore, were synthesized via a Schmidt rearrangement from their corresponding 1,2,3,4-tetrahydro-4-quinolones mediated by the NaN3/H2SO4 reaction conditions. Twelve of the obtained compounds were in vitro screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where compound 24a presented a remarkable activity against 58 of the 60 cancer cell lines, with the most important GI50 values ranging from 0.047 to 8.16 μM and LC50 values ranging from 9.4 to > 100 μM. Additionally, some of them were evaluated as antimalarial, antitrypanosomal and antileishmanial agents. The best antimalarial response was observed for compound 22g with an EC50 = 13.61 μg/mL for Plasmodium falciparum, while compound 24d exhibited high activity against Trypanosoma cruzi. and Leishmania (V) panamensis with EC50 = 2.78 μg/mL and 3.35 μg/mL respectively.

Synthesis and anticancer activity of novel curcumin-quinolone hybrids

A number of new curcumin-quinolone hybrids were synthesised from differently substituted 3-formyl-2-quinolones and vanillin and their in vitro cytotoxicity was determined on a panel of representative cell lines (A549, MCF7, SKOV3 and H460) using MTT assay. The most potent compound 14, was analysed for its mode of action using various cell biology experiments. SKOV3 cells treated with compound 14 showed distorted cell morphology under phase contrast imaging and induction of apoptosis was confirmed by Annexin V/PE assay. Further experiments on generation of reactive oxygen species (ROS) and cell cycle analysis revealed that these hybrids induce apoptosis by ROS generation and arrest cell cycle progression in S and G2/M phase.

Zn(OTf)2-catalyzed three component, one-pot cyclocondensation reaction of some new octahydroquinazolinone derivatives and access their bio-potential

An efficient synthesis of some new octahydroquinazolinone derivatives 4a-x by the cyclocondensation reaction of corresponding 2-thi(oxo)-1,2- dihydroquinoline-3-carbaldehyde 1a-e, 1,3-dicarbonyl compounds 2a-b, and substituted urea 3a-c using zinc triflat

A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 9. Synthetic Application of the 2-Chloroquinoline-3-carbaldehydes

The 2-chloro-groups of the title compounds have been replaced by H, I, OH, SR, Li, CO2H, CHO, Ph, piperidine, and N3 (giving a tetrazole).The aldehyde group has also been converted into oxime, hydrazone, and acrylic acid derivatives.From these and related

A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 5. The Synthesis of 2-Chloroquinoline-3-carbaldehydes

Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution.The reaction is shown to involve successive conversion of the acetanilide into an imidoyl chloride and then an N-(α-chlorovinyl)aniline.The latter enamine is diformylated at its β-position and subsequently cyclised to the chloroquinolinecarbaldehyde.The diformylated intermediates may be isolated in several cases and separately cyclised with polyphosphoric acid.