Alabaster, Colin T. published the artcile2(1H)-Quinolinones with cardiac stimulant activity. 1. Synthesis and biological activities of (six-membered heteroaryl)-substituted derivatives, Recommanded Product: (2-Amino-5-iodophenyl)methanol, the publication is Journal of Medicinal Chemistry (1988), 31(10), 2048-56, database is CAplus and MEDLINE.
A series of (six-membered heteroaryl)-substituted 2(1H)-quinolinones, e.g., I (R = H, R1 = pyridin-2-yl), were synthesized, and structure-activity relationships for cardiac stimulant activity were determined Most compounds were prepared by acidic hydrolysis of a heteroaryl-2-methoxyquinoline obtained by palladium-catalyzed cross-coupling methodol. Direct reaction of a pyridinylzinc reagent with a 6-haloquinolinone also proved successful. In anesthetized dogs, I (R = H, R1 = pyridin-3-yl)(II) (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-Me group into II reduced inotropic activity, whereas the 8-isomer I (R = Me, R1 = pyridin-3-yl)(III) proved to be the most potent member of the series. III and the 2,6-dimethylpyridinyl analog I (R = Me, R1 = 2,6-dimethylpyridin-3-yl)(IV) were approx. 6 and 3 times, resp., more potent than milrinone. Several quinolinones displayed pos. inotropic activity (decrease in QA interval) in conscious dogs after oral administration (1 mg/kg), and III and IV were again the most potent members of the series. IV (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 II, III, IV, and I (R = H, R1 = pyridin-4-yl) 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 IV, heart rate changed by less than 10 beats/min. In norepinephrine contracted rabbit femoral artery and saphenous vein, IV produced dose related (5 × 10-7 to 5 × 10-4 M) vasorelaxant activity. The combined cardiac stimulant and vasodilator properties displayed by IV, coupled with a lack of effect on heart rate, should be beneficial for the treatment of congestive heart failure.
Journal of Medicinal Chemistry published new progress about 53279-83-7. 53279-83-7 belongs to iodides-buliding-blocks, auxiliary class Iodide,Amine,Benzene,Alcohol, name is (2-Amino-5-iodophenyl)methanol, and the molecular formula is C7H8INO, Recommanded Product: (2-Amino-5-iodophenyl)methanol.
Referemce:
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