607-66-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-4-methylquinoline could be used as an intermediate in the synthesis of various pharmaceutical compounds for [application reason, e.g., treating bacterial infections or as a building block for developing new drugs].
Used in Chemical Research:
In the field of chemical research, 2-Hydroxy-4-methylquinoline might be utilized as a research compound for studying the properties and reactions of quinolone derivatives, potentially leading to the discovery of new chemical reactions or applications.
Used in Material Science:
2-Hydroxy-4-methylquinoline could be employed in material science as a component in the development of new materials with specific properties, such as luminescent materials or as part of sensor technologies.
[Please replace the placeholders [application reason] and the hypothetical uses with actual applications if they are provided in the source materials or known from other reliable sources.]

InChI:InChI=1/C10H9NO/c1-7-6-10(12)11-9-5-3-2-4-8(7)9/h2-6H,1H3,(H,11,12)

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 4437-65-4 2-mercapto-4-methylquinoline 
• 634-47-9 2-chloro-4-methylquinoline 
• 4053-40-1 4-methylquinoline 1-oxide 
• 108-24-7 acetic anhydride 
• 103264-22-8 4-methyl-quinoline-2-sulfonic acid 
• 587-96-2 3-difluoroboranyloxy-crotonic acid anilide 
• 101877-37-6 (E)-3-methyl-3-(benzylsulfanyl)-N-phenylpropenamide 
• 102-01-2 N-phenylacetoacetamide 
• 5234-26-4 N-(2-acetylphenyl)acetamide 
• 67-66-3 chloroform 
• 7732-18-5 water 
• 98-59-9 p-toluenesulfonyl chloride 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 634-47-9 2-chloro-4-methylquinoline 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 64658-04-4 2-bromo-4-methyl-quinoline 
• 90771-17-8 4-methyl-6-nitro-quinolin-2-ol 
• 15113-00-5 2-methoxy-4-methyl quinoline 
• 59-49-4 2-Benzoxazolinone 
• 19343-78-3 4-methyl-1,2,3,4-tetrahydroquinoline 
• 340296-87-9 (4-methyl-quinolin-2-yl)-o-tolyl-amine 
• 331711-88-7 4-methyl-N-(p-tolyl)quinolin-2-amine 
• 10562-04-6 4-methyl-N-phenylquinolin-2-amine 
• 125157-98-4 5,9,11-trimethyl-5H-indolo<2,3-b>quinoline 
• 40105-30-4 4-methylquinoline-2-carbaldehyde 
• 54965-59-2 2-chloro-4-methyl-6-nitroquinoline 
• 31128-02-6 phenyl-(4-methyl-6-nitro-quinolin-2-yl)amine 

Relevant academic research and scientific papers

A facile synthesis of novel 9-methyl[1,2,3]selenadiazoles[4,5-b]quinoline and 9-methyl[1,2,3]thiadiazole[4,5-b]quinoline as a new class of antimicrobial agents

2-chloro-4-methyl quinoline 2 on condensation with semicarbazide hydrochloride gave its semicarbazone. This on reaction with SeO2 and SOCl2 yielded a new class of novel selenadiazoles 4 and thiadiazoles 5, respectively. The structure of all the compounds were elucidated on the basis of elemental analysis, IR, 1H NMR, and the mass spectral data. Some derivatives of 9-methyl[1,2,3]selenadiazole[4,5-b] quinoline and 9-methyl[1,2,3]thiadiazole [4,5-b]quinoline have been screened for antimicrobial activities. Copyright Taylor & Francis Group, LLC.

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Computational and Synthetic approach with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S triple mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)

New substituted quinoline derivatives were designed and synthesized via a five-step modified Suzuki coupling reaction. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. All docking studies confirmed high potency and flexibility towards wild type as well as a mutated enzyme. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M/C797S and L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Most of the quinoline derivatives revealed a significant cytotoxic effect. The IC50 values of 4-(4-methylquinolin-2-yl)phenyl 4-(chloromethyl)benzoate (5j) were found to be 0.0042 μM, 0.02 μM, 1.91 μM, 3.82 μM and 3.67 μM while IC50 values of osimertinib were 0.0040 μM, 0.02 μM, ND, 0.99 μM and 1.22 μM, respectively. Compound 5j has shown excellent inhibitory activities against EGFR kinases triple mutant with IC 50 value 1.91 μM. It was observed that, compared to H1975, A549 and A431 cell lines, synthesized compounds significantly inhibited proliferation of the HCC827 cell line. These data suggested that synthesized compounds showed promising selective anticancer activity against tumor cells harboring EGFR Del E746-A750. The potency of compound 5j was compared through molecular dynamic simulations and an insilico ADMET study. QSAR models were generated and the best model was correctly compared with respect to predicted and observed activity of compounds. The built model will assist to design, refine and construct novel substituted quinoline derivatives as potent EGFR inhibitors in near future.

Free energy perturbation guided Synthesis with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)

Two different schemes of novel substituted quinoline derivatives were designed and synthesized via simple reaction steps and conditions. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. Free energy perturbations were carried out to determine the absolute binding free energy of a protein–ligand complex in the form of ΔGbinding, which in turn provided 4ab and 5ad as the most potential contenders through the structural enhancement in the determined initial scaffolds. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Compound 4ad (6-chloro-2-(isoindolin-2-yl)-4-methylquinoline) has shown excellent inhibitory activities against mutant EGFR kinase with IC50 value 0.91 μM. The potency of compounds 4ab, 4ad and 5ad was compared through an insilico ADMET study.

Metal-Free C-H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents

A novel metal-free C-H [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones has been established for the assembly of the privileged quinolinones and pyrrolyl-fused quinoxalinones. Entirely differing from the existing reports, the dioxazolones herein behave with an innovative chemistry and first emerge as carbonylating reagents to participate in annulation reactions. Moreover, this process features exceedingly simple operation (only solvent) and tolerates both vinyl and aryl substrates. Comprehensive mechanistic studies indicate that the formed isocyanate intermediate plays a crucial role in enabling the carbonylation annulation.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Synthesis and antileishmanial evaluation of thiazole orange analogs

Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.

HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst

A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.

Lactamization of alkenyl C-H bonds to generate 2-quinolinones with triphosgene

A simple and easy-going method is developed to synthesize the analogues of 2-quinolinones by using triphosgene (BTC) as the carbonyl source. In these reactions, both the toxic carbon monoxide (CO) and phosgene are avoided and the 2-quinolinones are obtained in moderate to good yields under mild conditions, all of which are anticipated to be meaningful in both industry and laboratory.