67984-95-6Relevant academic research and scientific papers
4-hydroxy-2-quinolones. 178*. irreversible chemical modification of chinoxicaine at the position 4 of the quinolone ring
Ukrainets,Tkach,Kravtsova,Mamchur,Kovalenko
, p. 850 - 855 (2010)
While continuing our investigation in improving the pharmaceutical activities of the local anesthetic Chinoxicaine we have studied the irreversible replacement of its 4-OH group for bioisosteric fragments. For this purpose the synthesis of a series of 4-R-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-(diethylamino)ethylamide hydrochlorides has been carried out. The experimental data of the local anesthetic properties of the compounds obtained are given and discussed.
Synthesis and evaluation of novel 2-oxo-1,2-dihydro-3-quinolinecarboxamide derivatives as serotonin 5-HT4 receptor agonists
Suzuki,Ohuchi,Asanuma,Kaneko,Yokomori,Ito,Isobe,Muramatsu
, p. 2003 - 2008 (2007/10/03)
A series of N-azabicycloalkyl-1-alkyl-2-oxo-1,2-dihydro-3-quinolinecarboxamides were synthesized and tested for serotonin 5-HT4 receptor-stimulating effects in the regulation of electrically-evoked contraction in guinea pig muscle. Among them, N-azabicycloalkyl-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide (8c, 9c, 10c, 11c, 12c) exhibited potent serotonin 5-HT4 receptor-stimulating activity. The most potent compound, N-(endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3 -quinolinecarboxamide (8c, ED50= 36.3 nM), was seven times as active as cisapride, while 8c had no affinity for 5-HT,1A, 5-HT1D, D2, muscarinic M2 or muscarinic M3 receptors even at 10 μM. Compound 8c stimulated digestive tract motility in conscious fed dogs (1.0 mg/kg p.o.).
Disproportionation in Hydrolysis of Pyrimidoquinoline-2(3H),4(10H)-diones (5-Deazaflavins)
Yoneda, Fumio,Sakuma, Yoshiharu,Koshiro, Akira
, p. 293 - 296 (2007/10/02)
Treatment of 5-deazaflavins with concentrated aqueous potassium hydroxide led to the exclusive formation of 1,5-dihydro-5-deazaflavins and 1,5-dihydro-5-deazaflavin-5-ones via intermolecular oxidation-reduction between initially formed 5-hydroxy-1,5-dihydro-5-deazaflavins and unchanged 5-deazaflavins; under dilute alkaline conditions the reverse oxidation-reduction between 1,5-dihydro-5-deazaflavins and 1,5-dihydro-5-deazaflavin-5-ones occurred to form the original 5-deazaflavins and 5-hydroxy-1,5-dihydro-5-deazaflavins, which were oxidized to 1,5-dihydro-5-deazaflavin-5-ones by air.When hydrolysis was carried out with dilute alkaline solution, the corresponding 2-oxoquinoline-3-carboxylic acids were obtained besides the disproportionation products 1,5-dihydro-5-deazaflavins and 1,5-dihydro-5-deazaflavin-5-ones.This disproportionation and hydrolytic scission at the 2-position complete with each other.Higher concentrations of hydroxide ion favoured the formation of the reduced 5-deazaflavins and 5-ketones by disproportionation and reduced the proportion of 2-quinolones formed by hydrolytic scission.
