219949-95-8

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry Research:
ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE is used as a precursor or intermediate for the synthesis of various drugs and pharmaceuticals, contributing to the development of new therapeutic agents.
Used in Anti-Inflammatory Applications:
In the pharmaceutical industry, ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE is used as an anti-inflammatory agent, potentially aiding in the treatment of various inflammatory conditions by reducing inflammation and associated symptoms.
Used in Anti-Cancer Applications:
ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE is used as an anti-cancer agent, playing a role in the development of chemotherapeutic drugs that target and combat cancer cells, potentially leading to improved treatment options for cancer patients.
Used in Antimicrobial Applications:
In the field of antimicrobial research, ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE is used as an antimicrobial agent, contributing to the development of new antibiotics and antifungal agents to combat resistant microbial strains.
Used in Organic Compound Development:
ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE is used in the development of various organic compounds, serving as a key component in the synthesis of a range of chemical products for diverse applications across different industries.

Upstream product

• 759-65-9 diethyl oxalpropionate 
• 408532-32-1 diethyl 2‐methyl-3‐(phenylimino)succinate 
• 62-53-3 aniline 
• 59946-31-5 C₁₅H₁₉NO₄ 
• 86119-84-8 phosphoric acid 

Downstream Products

• 858488-66-1 3-Methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid 
• 1379615-61-8 4‐chloro-3-methyl‐2‐(1‐(4‐(trifluoromethoxy)benzyl)-1H‐pyrazol‐4‐yl)quinoline 
• 1379615-35-6 3-methyl-2-(1-(4‐(trifluoromethoxy)benzyl)‐1H‐pyrazol‐4-yl)quinolin‐4(1H)‐one 
• 63136-60-7 4-chloro-3-methylquinoline 
• 1616959-50-2 2-(biphenyl-4-ylcarbamoyl)-3-methylquinoline-4-carboxylic acid 
• 1616959-72-8 N-biphenyl-4-yl-4-hydroxy-3-methylquinoline-2-carboxamide 
• 1616959-90-0 C₂₄H₁₇N₃O 
• 1616959-81-9 C₂₄H₁₇F₃N₂O₄S 
• 64965-46-4 3-methylquinolin-4-ol 
• 923585-65-3 (R)-4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]-3-methylquinoline-2-carboxylic acid ethyl ester 
• 24782-23-8 4-chloro-3-methylquinoline-2-carboxylic acid ethyl ester 
• 858488-66-1 4-hydroxy-3-methylquinoline-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Activity of Burkholderia-Related 4-Hydroxy-3-methyl-2-alkenylquinolines (HMAQs) and Their N-Oxide Counterparts

The Burkholderia genus offers a promising potential in medicine because of the diversity of biologically active natural products encoded in its genome. Some pathogenic Burkholderia spp. biosynthesize a specific class of antimicrobial 2-alkyl-4(1H)-quinolo

4-QUINOLINONE ANTIBACTERIAL COMPOUNDS

The present invention relates to the following compounds (I) wherein the integers are as defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of tuberculosis (e.g. in combination).

Potent Antimalarial 2-Pyrazolyl Quinolone bc1 (Qi) Inhibitors with Improved Drug-like Properties

A series of 2-pyrazolyl quinolones has been designed and synthesized in 5-7 steps to optimize for both in vitro antimalarial potency and various in vitro drug metabolism and pharmacokinetics (DMPK) features. The most potent compounds display no cross-resistance with multidrug resistant parasite strains (W2) compared to drug sensitive strains (3D7), with IC50 (concentration of drug required to achieve half maximal growth suppression) values in the range of 15-33 nM. Furthermore, members of the series retain moderate activity against the atovaquone-resistant parasite isolate (TM90C2B). The described 2-pyrazoyl series displays improved DMPK properties, including improved aqueous solubility compared to previously reported quinolone series and acceptable safety margin through in vitro cytotoxicity assessment. The 2-pyrazolyl quinolones are believed to bind to the ubiquinone-reducing Qi site of the parasite bc1 complex, which is supported by crystallographic studies of bovine cytochrome bc1 complex.

The synthesis of quinolone natural products from pseudonocardia sp.

The synthesis of four quinolone natural products from the actinomycete Pseudonocardia sp. is reported. The key step involved a sp2-sp3 Suzuki-Miyaura reaction between a common boronic ester lateral chain and various functionalised quinolone cores. The quinolones slowed growth of E. coli and S. aureus by inducing extended lag phases. The total synthesis of four quinolone natural products is reported. The quinolones were synthesised in a highly efficient and direct manner from various readily prepared quinolone cores and a common boronic ester lateral chain. The key step involved a challenging sp2-sp3 Suzuki-Miyaura reaction.

Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents

In continuation of our research for novel human dihydroorotate dehydrogenase (hDHODH) inhibitors, herein we reported design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives. Human DHODH enzyme inhibition a

New iodinated quinoline-2-carboxamides for SPECT imaging of the translocator protein

With the aim of developing new SPECT imaging agents for the translocator protein (TSPO), a small library of iodinated quinoline-2-carboxamides have been prepared and tested for binding affinity with TSPO. N,N-Diethyl-3-iodomethyl-4-phenylquinoline-2-carboxamide was found to have excellent affinity (Ki 12.0 nM), comparable to that of the widely used TSPO imaging agent PK11195.

Design and synthesis of 4-quinolinone 2-carboxamides as calpain inhibitors

Calpains are involved in a variety of calcium-regulated cellular processes, such as signal transduction, cell proliferation, differentiation, and apoptosis. Excessive calpain activation contributes to serious cellular damage and has been reported in many pathological conditions. 4-Quinolinone 2-carboxamide derivatives were prepared and evaluated for μ-calpain inhibitory activities. Of the compounds synthesized, 3a and 3k, which possess a primary amide and 4-methoxyphenethyl amide at P1′ region, were found to most potently inhibit μ-calpain with IC50 values of 0.71 ± 0.07 and 0.73 ± 0.23 μM, respectively. On the other hand, the incorporation of pyridine-containing amides decreased inhibitory activity.

Structure-activity relationship of quinoline derivatives as potent and selective α2c-adrenoceptor antagonists

Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human α2- adrenoceptor subtypes (α2A, α2B, and α2C). A number of compounds with good antagonist potencies against the α2C-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]quinolin-3-yl}methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the α2c-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the α2C- adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

Novel ester or amide derivatives

An ester or amide derivative represented by the general formula (I) or a pharmaceutically acceptable salt thereof. Particularly, an ester or amide derivative of 4-oxo-1,4-dihydroqunoline-2-carboxylic acid represented by the general formula (I′) or (I″), o

1-PROPANOL AND 1-PROPYLAMINE DERIVATIVES AND THEIR USE AS GLUCOCORTICOID LIGANDS

Compounds of Formula (I) wherein R1, R2 R3, R4, R5, R6, and X are as defiend herein for Formula (IA) and Formula (IB), or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocoricoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.