28448-12-6

Basic information

• Product Name: 3-quinolinecarbonitrile, 1,2-dihydro-4-methyl-2-oxo-
• Synonyms: 3-quinolinecarbonitrile, 1,2-dihydro-4-methyl-2-oxo-;4-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile
• CAS NO: 28448-12-6
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.19402
• Mol File: 28448-12-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 399.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• PKA: 9.76±0.70(Predicted)
• CAS DataBase Reference: 3-quinolinecarbonitrile, 1,2-dihydro-4-methyl-2-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-quinolinecarbonitrile, 1,2-dihydro-4-methyl-2-oxo-(28448-12-6)
• EPA Substance Registry System: 3-quinolinecarbonitrile, 1,2-dihydro-4-methyl-2-oxo-(28448-12-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 28448-12-6(Hazardous Substances Data)

Usage

General Description

3-quinolinecarbonitrile, 1,2-dihydro-4-methyl-2-oxo- is a chemical compound with the molecular formula C10H8N2O. It is a derivative of quinoline and is commonly used in the pharmaceutical industry for the synthesis of various pharmaceuticals and agrochemicals. This chemical has also been studied for its potential biological and pharmacological activities, such as antimicrobial and anticancer properties. Its structure and properties make it a valuable intermediate in the production of a wide range of organic compounds, making it an important building block in chemical synthesis.

Upstream product

• 551-93-9 2-aminoacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 
• 613-89-8 2-Aminoacetophenone 
• 1016641-95-4 C₁₁H₁₀N₂O₂ 

Downstream Products

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 101617-94-1 2?chloro?3?cyano?4?methylquinoline 

Relevant articles and documents

Enantioselective Direct Vinylogous Allylic Alkylation of 4-Methylquinolones under Iridium Catalysis

The first enantioselective vinylogous allylic alkylation of 4-methylquinolones has been developed. This iridium-catalyzed reaction introduces an allyl group at the γ-position of 4-methyl-2-quinolones with exclusive branched selectivity and an excellent level of enantioselectivity. This in turn allows for the enantioselective synthesis of γ-allylquinolines and related nitrogenous heterocycles. This is the first application of 4-methylquinolones in an enantioselective transformation.

Polycyclic Aromatic Alkaloids, III: Synthesis of Perlolidine

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Discovery of quinolone derivatives as antimycobacterial agents

Tuberculosis (TB), an infectious disease caused byMycobacterium tuberculosis(M. tuberculosis), is an important public health issue. Current first-line drugs administered to TB patients have been in use for over 40 years, whereas second-line drugs display strong side effects and poor compliance. Additionally, designing effective regimens to treat patients infected with multi- and extremely-drug-resistant (MDR and XDR) strains of TB is challenging. In this report, we screened our compound library and identified compound1with antituberculosis activity and a minimal inhibitory concentration (MIC) againstM. tuberculosisof 20 μg mL?1. Structure optimization and the structure-activity relationship of1as the lead compound enabled the design and synthesis of a series of quinolone derivatives,6a1-6a2,6b1-6b36,6c1,6d1-6d14,7a1-7a2,7b1-7b2,7c1,8a1-8a5,9a1-9a4and10a1-10a6. These compounds were evaluatedin vitrofor anti-tubercular activity against theM. tuberculosisH37Rv strain. Among them, compounds6b6,6b12and6b21exhibited MIC values in the range of 1.2-3 μg mL?1and showed excellent activity against the tested MDR-TB strain (MIC: 3, 2.9 and 0.9 μg mL?1, respectively). All three compounds were non-toxic toward A549 and Vero cells (>100 and >50 μg mL?1, respectively). In addition, an antibacterial spectrum test carried out using compound6b21showed that this compound specifically inhibitsM. tuberculosis. These can serve as a new starting point for the development of anti-TB agents with therapeutic potential.

QUINOLINONE DERIVATIVES

HIV inhibitory compounds of formula (I) including the stereoisomeric forms thereof, the pharmaceutically acceptable salts, and pharmaceutically acceptable solvates thereof; wherein R1 is cyano; R2 is H, C1-6alkyl, trifluoromethyl, amino, mono- or di-C1-6alkylamino, C1-6alkylamino wherein the C1-6alkyl group can be substituted; X1 is CH or N; R3 is phenyl or pyridyl, each unsubstituted or substituted; R4 is H, C1-6alkyl, (C1-6alkylcarbonyla mino)C1-6alkyl-, Ar, potionally substituted thienyl, furanyl, pyridyl, pyrimidyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazo lyl, oxazolyl, thiazolyl, halo, trifluoromethyl, hydroxy, C1-6alkyloxy, -OPO(OH)2, amino, aminocarbonyl, cyano, -Y1-R6, -Y1-Alk-R6, or -Y1-Alk-Y2-R7; R5 is H, halo, hydroxy or C1-6alkyloxy; or R4 and R5 form -O-CH2-O-; Y1 is O or NR8; Y2 is O or NR9; Alk is bivalent C1-6alkyl; R6 is pyrrolidinyl, piperidinyl, morpho linyl, piperazinyl, 4-C1 -6alkylpiperazinyl, 4-(C1-6alkylcarbonyl)piperazinyl, pyridyl, or imidazolyl; R7 is H, C1-6alkyl, hydroxyC1 -6alkyl, C1-6alkylcarbonyl; R8 and R9 are H or C1-6alkyl; Ar is optionally substituted phenyl; pharmaceut ical compositions comprising the above compounds (I) as active ingredient.