99465-03-9

Usage

Uses

Used in Pharmaceutical Research:
6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile is used as a key intermediate in the synthesis of diverse pharmaceuticals and bioactive molecules. Its unique structure and reactivity enable the creation of a wide range of chemical compounds with potential biological and medicinal applications.
Used in Organic Synthesis:
In the field of organic synthesis, 6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile serves as a valuable building block for the preparation of various chemical compounds. Its functional groups allow for further modification and functionalization, making it a useful component in the synthesis of complex organic molecules.
Used in Antimicrobial Agents Development:
6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile has been reported to exhibit antibacterial and antifungal activities. Its potential use in the development of new antimicrobial agents makes it a promising candidate for addressing the growing issue of antibiotic resistance and the need for novel antifungal treatments.
Used in Antitumor and Antiviral Research:
6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile has also been studied for its potential antitumor and antiviral properties. Its ability to target and inhibit the growth of cancer cells and viral replication makes it a valuable tool in the search for new therapeutic agents to combat cancer and viral infections.

InChI:InChI=1/C10H5BrN2O/c11-8-1-2-9-6(4-8)3-7(5-12)10(14)13-9/h1-4H,(H,13,14)

Upstream product

• 36926-82-6 2-oxo-1,2-dihydroquinoline-3-carbonitrile 

Downstream Products

• 99465-04-0 6-bromo-2-chloro-3-cyanoquinoline 

Relevant academic research and scientific papers

2(1H)-Quinolinones with cardiac stimulant activity. 1. Synthesis and biological activities of (six-membered heteroaryl)-substituted derivatives

A series of (six-membered heteroaryl)-substituted 2(1H)-quinolinones was synthesized, and structure-activity relationships for cardiac stimulant activity were determined. Most compounds were prepared by acidic hydrolyisis of a heteroaryl-2-methoxyquinoline obtained by palladium-catalyzed cross-coupling methodology. Direct reaction of a pyridinylzinc reagent with a 6-haloquinolinone also proved successful. In anesthetized dogs, 6-pyridin-3-yl-2(1H)-quinolinone (3; 50 μg/kg) displayed greater inotropic activity (percentage increase in dP/dt max) than positional isomers, and potency was maintained with either mono- or di- alkylpyridinyl substituents. Introduction of a 4- or 7- methyl group into 3 reduced inotropic activity, whereas the 8-isomer proved to be the most potent member of the series. Compound 26 and the 2,6-dimethylpyridinyl analogue (27 were approximately 6 and 3 times more potent than milrinone. Several quinolinones displayed positive inotropic activity (decrease in QA interval) in conscious dogs after oral administration (1 mg/kg), and 26, 27 were again the most potent members of the series. Compound 27 (0.25, 0.5, 1.0 mg/kg po) demonstrated dose-related cardiac stimulant activity, which was maintained for at least 4 h. No changes in heart rate were observed. Compounds 3, 4, 26, and 27 also selectively stimulated the force of contraction, rather than heart rate, in the dog heart-lung preparation. For a 50% increase in dP/dt max with 27, heart rate changed by less than 10 beats/min. In norepinephrine contracted rabbit femoral artery and saphenous vein, 27 produced dose related (5 x 10-7 to 5 x 10-4 M) vasorelaxant activity. The combined cardiac stimulant and vasodilator properties displayed by 27, coupled with a lack of effect on heart rate, should be beneficial for the treatment of congestive heart failure.

Quinolone inotropic agents

A heterocyclic-substituted 2-quinolone compound of the formula: STR1 or a pharmaceutically-acceptable salt thereof, wherein "Het" is an optionally substituted 5-or 6-membered monocyclid aromatic heterocyclic group attached by a carbon atom to the 5-, 6-, 7- or 8- position of the quinolone nucleus; R, which is attached to the 5-, 6-, 7- or 8- position, is hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulphinyl, C1 -C4 alkylsulphonyl, halo, CF3, hydroxy, hydroxymethyl, or cyano; R1 is hydrogen, cyano (C1 -C4 alkoxy)carbonyl, C1 -C4 alkyl, nitro, halo, --NR3 R4 or --CONR3 R4 where each of R3 and R4 is hydrogen or C1 -C4 alkyl or R3 and R4 together with the nitrogen atom to which they are attached form a saturated 5- or 6-membered heterocyclic group optionally containing a further heteroatom or group selected from O, S and N--R5 where R5 is hydrogen or C 1 -C4 alkyl; R2 is hydrogen, C1 -C4 alkyl, or 2-hydroxyethyl; Y is hydrogen or C1 -C4 alkyl; and the dotted line between the 3- and 4- positions represents an optional bond. The compounds are inotropic agents useful as cardiac stimulants in the treatment of congestive heart failure.