16062-69-4Relevant academic research and scientific papers
Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones
Zhou, Zebiao,Huang, Bin,Cai, Mingzhong
, p. 3150 - 3163 (2021/08/30)
A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance and good to excellent yields. This supported palladium complex can be readily separated from the product and recovered by a simple filtration of the reaction solution and reused up to seven times with almost consistent catalytic efficiency.
Microwave assisted synthesis and molecular docking studies of some 4 (3H)-quinazolinone derivatives as inhibitors of human gammaaminobutyric acid receptor, the GABA (A)R-BETA3 homopentamer
Amrutkar, Rakesh Devidas,Ranawat, Mahendra Sing
, p. 453 - 461 (2021/03/26)
Background: Quinazolines and quinazolinones constitute a major class of biologically active molecules, both from natural and synthetic sources. The quinazolinone moiety is an important pharmacophore showing many types of pharmacological activities as show
A general palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones from 2-bromoanilines and acid anhydrides
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
supporting information, p. 12599 - 12602 (2012/11/07)
(C), its (O)K! An efficient palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones has been developed (see scheme). By starting from 2-bromoanilines and acid anhydrides, the corresponding products were isolated in good yields. Copyright
Synthesis of a novel series of 2,3-disubstituted quinazolin-4(3H)-ones as a product of a nucleophilic attack at C(2) of the corresponding 4H-3,1-benzoxazin-4-one
El-Hashash, Mahr A.,El-Badry, Yaser A.
experimental part, p. 389 - 396 (2011/04/25)
A new series of 2,3-disubstituted quinazolin-4(3H)-one derivatives was synthesized by nucleophilic attack at C(2) of the corresponding key starting material 2-propyl-4H-3,1-benzoxazin-4-one (Scheme 2). The reaction proceeded via amidinium salt formation (Scheme 3) rather than via an N-acylanthranilimide. The structure of the prepared compounds were elucidated by physical and spectral data like FTIR, 1H-NMR, and mass spectroscopy.
Design, synthesis and potential 6 Hz psychomotor seizure test activity of some novel 2-(substituted)-3-{[substituted]amino}quinazolin-4(3H)-one
Kumar, Praveen,Shrivastava, Birendra,Pandeya, Surendra N.,Stables, James P.
experimental part, p. 1006 - 1018 (2011/04/24)
Thirty new 2-(substituted)-3-{[substituted]amino}quinazolin-4(3H)-one were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity of the titled compounds was assessed using the 6 Hz psychomotor seizure test. The most active compound of the series was 3-({(E)-[3-(4-chloro-3-methylphenoxy)phenyl]methylidene}amino) -2-phenylquinazolin-4(3H)-one PhQZ 7, which showed 100% protection (4/4, 0.5 h) and 75% protection (3/4, 0.25 h) at a dose of 100 mg/kg in mice. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties. Titled compounds have also exhibited good binding properties with epilepsy molecular targets such as glutamate, GABA (A) delta and GABA (A) alpha-1 receptors, in Lamarckian genetic algorithm based flexible docking studies.
Synthesis and biological evaluation of some new 4(3H)-quinazolinone derivatives as non-classical antifolate
El-Hashash,El-Metwally,Eissa,El-Gohary
, p. 777 - 790 (2013/05/21)
LL living cell need tetrahydrofolate cofactor for the synthesis of purines, some amino acid and thymidine. Most bacteria and plant produce this folate cofactor by de novo biosynthesis. Compounds that interfere with this pathway, antifolate agents have found use as anticancer. Thus, the 2-propyl-4H-3,1- benzoxazin-4-one (2) was synthesized and allowed to interaction with Ammonium acetate or formamide afforded-2-propylquinazolin-4(3H)-one (3). Behaviour of quinazolinone towards carbon electrophiles namely, aromatic aldehyde, chloroacetylchloride, and ethylchloroacetate has been investigated and all the synthesized compounds were tested as anti-cancer in National Cancer Institute (NCI) in USA.
Silica-bound benzoyl chloride mediated the solid-phase synthesis of 4H-3, 1-benzoxazin-4-ones
Rad-Moghadam, Kurosh,Rouhi, Somayeh
experimental part, (2010/04/22)
The solid-phase synthesis of 4H-3, 1-benzoxazin-4-ones was achieved using silica-bound benzoyl chloride (SBBC) as dehydrating agent in reaction with 2-acylaminobenzoic acids. The silica-grafted reagent (SBBC) was simply recovered after reaction and reused several times.
Synthesis, structure-activity relationships, and biological profiles of a quinazolinone class of histamine H3 receptor inverse agonists
Nagase, Tsuyoshi,Mizutani, Takashi,Ishikawa, Shiho,Sekino, Etsuko,Sasaki, Takahide,Fujimura, Takashi,Ito, Sayaka,Mitobe, Yuko,Miyamoto, Yasuhisa,Yoshimoto, Ryo,Tanaka, Takeshi,Ishihara, Akane,Takenaga, Norihiro,Tokita, Shigeru,Fukami, Takehiro,Sato, Nagaaki
supporting information; experimental part, p. 4780 - 4789 (2009/07/25)
A new series of quinazolinone derivatives was synthesized and evaluated as nonimidazole H3 receptor inverse agonists. 2-Methyl-3-(4-{[3-(1- pyrrolidinyl)propyl]oxy}phenyl)-5-(trifluoromethyl)-4(3H)-quinazolinone (1) was identified as a promising derivative for further evaluation following optimization of key parameters. Compound 1 has potent H3 inverse agonist activity and excellent selectivity over other histamine receptor subtypes and a panel of 115 unrelated diverse binding sites. Compound 1 also shows satisfactory pharmacokinetic profiles and brain penetrability in laboratory animals. Two hours after oral administration of 30 mg/kg of 1 to SD rats, significant elevation of brain histamine levels was observed where the brain H3 receptor was highly occupied (>90%). On the basis of species differences in P-glycoprotein (P-gp) susceptibility of 1 between human and rodent P-gps, the observed rodent brain permeability of 1 is significantly limited by P-gp mediated efflux in rodents, whereas the extent of P-gp mediated efflux in humans should be very small or negligible. The potential of 1 to be an efficacious drug was demonstrated by its excellent brain penetrability and receptor occupancy in P-gp-deficient CF-1 mice.
Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents
Mahindroo, Neeraj,Ahmed, Zabeer,Bhagat, Asha,Bedi, Kasturi Lal,Khajuria, Ravi Kant,Kapoor, Vijay Kumar,Dhar, Kanaya Lal
, p. 347 - 368 (2007/10/03)
The series of vasicine (1) analogues, an alkaloid from Adhatoda vasica Nees., were synthesized with changes in A, B or C rings. Compounds 3-19 were evaluated for in vitro bronchodilatory activity using isolated guinea pig tracheal chain. Compounds 3-8 were also synthesized in good yields using microwave-mediated synthesis under solvent free conditions. Compounds 5 and 8 with seven-member C ring were more active than etofylline and caused 100% relaxation of both the histamine and acetylcholine pre-contracted guinea pig tracheal chain. The structure-activity relationship studies showed that the quinazoline and oxo functionalities were essential for activity. The compounds without C ring and instead having aliphatic and phenyl substitutions in B ring showed relaxation against histamine pre-contracted tracheal chain only, 2-methyl substituted analogues, 12 and 13, being most active with 100% relaxation effect. Birkhaeuser Boston 2006.
