4005-05-4Relevant academic research and scientific papers
Synthesis and anticonvulsant activity of novel quinazolin-4(3H)-one derived pyrazole analogs
Alagarsamy, Veerachamy,Saravanan, Govindaraj
, p. 1711 - 1722 (2013/07/26)
Eighteen novel 6,8-(dibromo/unsubstituted)-2-(methyl/phenyl)-3-(4-(5- (substitutedphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carbonyl)phenyl) -quinazolin-4(3H)-ones 4a-4r were designed and synthesized in good yield. Antiepileptic screening of the title compounds was performed using MES and scPTZ seizures tests while the neurotoxicity was determined by rotorod test. In the preliminary screening, compounds 4d, 4e, 4p, 4q, and 4r were found active in MES model, while 4a, 4d, 4f, 4m, and 4p showed significant antiepileptic activity in scPTZ model. Further, all these eight compounds were administered to rats and compounds 4e, 4p, and 4q showed better activity than Phenytoin in oral route. Among these compounds 4p revealed protection in MES after i.p. administration at a dose of 30 mg/kg (0.5 h) and 100 mg/kg (4 h). The compound 4p also provided protection in the scPTZ at a dose of 100 mg/kg (0.5 h) and 300 mg/kg (4 h).
Quinazolin-4-one derivatives: A novel class of noncompetitive NR2C/D subunit-selective N-methyl-D-aspartate receptor antagonists
Mosley, Cara A.,Acker, Timothy M.,Hansen, Kasper B.,Mullasseril, Praseeda,Andersen, Karen T.,Le, Phuong,Vellano, Kimberly M.,Br?uner-Osborne, Hans,Liotta, Dennis C.,Traynelis, Stephen F.
supporting information; experimental part, p. 5476 - 5490 (2010/11/16)
We describe a new class of subunit-selective antagonists of N-methyl d-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family of compounds does not exert action on the agonist binding site of the receptor or block the channel pore. The compounds described here resemble CP-465,022 ((S)-3-(2-chlorophenyl)-2-[2-(6-diethylaminomethyl-pyridin-2-yl)-vinyl] -6-fluoro-3H-quinazolin-4-one), a noncompetitive antagonist of AMPA-selective glutamate receptors. However, modification of ring substituents resulted in analogues with greater than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors. Furthermore, within this series of compounds, analogues were identified with 50-fold selectivity for recombinant NR2C/D-containing receptors over NR2A/B containing receptors. These compounds represent a new class of noncompetitive subunit-selective NMDA receptor antagonists.
Efficient solid phase synthesis of diverse quinazolinones
Makino,Suzuki,Nakanishi,Tsuji
, p. 1670 - 1672 (2007/10/03)
Various quinazolinones were synthesized by cyclocondensation of anthranilamides with a variety of orthoformates on solid supports. Alkyl, aryl and alkoxy groups can substitute at 2 position of quinazolines with this method. The reactions proceeded smoothly under mild acidic conditions and the products exhibited excellent purity. Unlike previously reported solid phase quinazolinone syntheses, this synthetic strategy does not require an oxidation step. The approach is applicable to the synthesis of a wide range of quinazolinones, including molecules that are susceptible to oxidation.
Synthesis of Some New 2-Aryl-3-Hetaryl-4(3H) Quinazolones
Dash, B.,Dora, E. K.,Panda, C. S.
, p. 835 - 836 (2007/10/02)
2-Aryl (alkyl)-benzoxazin-4-ones (I, R = CH3, C6H5, C6H5CH2, p-NO2C6H4) are condensed with 2-amino hetaryls (pyridyl, pyrimidyl, thiazolyl), 1 and 2-amino anthraquinones, p-amino acetophenone and 1,2-diamines like ethylene diamine and o-phenylene diamine.The products are obtained in excellent yields and are characterised by infrared and elemental analysis.
