1186230-86-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Oxo-1,4-dihydroquinoline-7-carbonitrile is used as a key intermediate in the synthesis of bioactive molecules for the development of new pharmaceuticals. Its unique structure and properties make it a promising candidate for the design and development of drugs targeting various diseases.
Used in Medicinal Chemistry Research:
4-Oxo-1,4-dihydroquinoline-7-carbonitrile is utilized as a starting material in medicinal chemistry research to explore its anti-cancer and anti-inflammatory activities. Its potential to modulate biological pathways and target specific enzymes or receptors makes it a valuable compound for the development of novel therapeutic agents.
Used in Drug Design:
4-Oxo-1,4-dihydroquinoline-7-carbonitrile is employed as a structural motif in drug design to enhance the potency and selectivity of pharmaceutical compounds. Its incorporation into drug molecules can improve their pharmacokinetic and pharmacodynamic properties, leading to more effective treatments for various diseases.
Used in Chemical Synthesis:
4-Oxo-1,4-dihydroquinoline-7-carbonitrile serves as a versatile building block in chemical synthesis, enabling the preparation of a wide range of organic compounds with diverse applications. Its reactivity and functional groups allow for various synthetic transformations, facilitating the development of new chemical entities with potential applications in various industries.

Upstream product

• 1186230-83-0 3-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile 
• 118078-26-5 7-cyano-4-hydroxyquinoline-3-carboxylic acid 
• 63463-18-3 ethyl 7-cyano-4-hydroxyquinoline-3-carboxylate 
• 59551-10-9 diethyl 2-[((3-cyanophenyl)amino)methylene]malonate 
• 2237-30-1 m-cyanoaniline 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 927829-33-2 1-(4-cyanophenyl)-3-dimethylamino-2-propen-1-one 

Downstream Products

• 181950-55-0 4-chloroquinoline-7-carbonitrile 
• 1253790-96-3 4-aminoquinoline-7-carbonitrile 

Relevant academic research and scientific papers

Co(III)-Catalyzed Enaminone-Directed C-H Amidation for Quinolone Synthesis

We report herein the development of a Co(III)-catalyzed enaminone-directed C-H amidation method for synthetic access to quinolones, an important heterocyclic scaffold for diverse pharmaceutically active structures. The C-H coupling with dioxazolones and subsequent deacylation of an installed amide group allow consecutive C-N coupling generation of quinolones with wide-ranging compatible substituent patterns.

HETEROCYCLIC COMPOUNDS

The present invention relates to compounds of the general formula (1) wherein the variables are defined as given in the description and claims. The invention further relates to uses of and to, processes and intermediates related to compounds of the general formula (I), wherein Q is wherein the substituents of I, Ia and Ib are as defined in description and claims.

Structure-activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (log K) and inhibition of β-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, log K values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (π) of the group X. The log K values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% β-hematin inhibitory activity (log BHIA50) was found to correlate with log K and either meta (σm) or para (σp) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that log K values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of β-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible.

Regioselective synthesis of quinolin-4-ones by pyrolysis of anilinomethylene derivatives of Meldrum's acid

Electron-rich and electron-deficient anilinomethylene derivatives of Meldrum's acid cyclize equally efficiently to quinolin-4-ones via imidoylketene intermediates under flash vacuum pyrolysis (FVP) conditions. Georg Thieme Verlag Stuttgart.