An Efficient One-Pot Access to Quinazolinone Derivatives Using TiO2 Nanoparticles as Catalyst: Synthesis and Vasorelaxant Activity Evaluation

被引:22
作者
Khalafi-Nezhad, Ali [1 ]
Haghighi, Saghar Mowlazadeh [1 ]
Purkhosrow, Azar [2 ]
Panahi, Farhad [1 ]
机构
[1] Shiraz Univ, Shiraz 71454, Iran
[2] Shiraz Univ Med Sci, Sch Med, Dept Pharmacol, Cardiovasc Pharmacol Res Lab, Shiraz 71454, Iran
关键词
quinazolinone; multicomponent reaction; TiO2; nanoparticles; heterogeneous catalyst; vasorelaxant activity; SOLVENT-FREE CONDITIONS; 4(3H)-QUINAZOLINONE DERIVATIVES; HYDROGEN-PEROXIDE; HETEROCYCLIC SYNTHESIS; MICROWAVE IRRADIATION; DEPRESSANT ACTIVITY; CASCADE SYNTHESIS; RECEPTOR; DESIGN; NUCLEOSIDE;
D O I
10.1055/s-0031-1290610
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of quinazolinone derivatives were successfully synthesized, via a three-component condensation reaction between anthranilic acid, acetic anhydride, and amines. This process was accomplished in the presence of catalytic amount of titanium dioxide nanoparticles (nano-TiO2), under solvent-free conditions. The synthesized compounds were evaluated for their vasorelaxant activity as they revealed a range of activities on the isolated thoracic rat aorta.
引用
收藏
页码:920 / 924
页数:5
相关论文
共 59 条
[1]   A novel, one-pot, solvent-, and catalyst-free synthesis of 2-aryl/alkyl-4(3H)-quinazolinones [J].
Adib, Mehdi ;
Ansari, Samira ;
Mohammadi, Ali ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2010, 51 (01) :30-32
[2]   A modified synthesis of iodoazidoaryl prazosin [J].
Andrus, MB ;
Mettath, SN ;
Song, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (23) :8284-8286
[3]   Antimicrobial Activity of Tryptanthrins in Escherichia coli [J].
Bandekar, Pooja P. ;
Roopnarine, Keir Alekseii ;
Parekh, Virali J. ;
Mitchell, Thomas R. ;
Novak, Mark J. ;
Sinden, Richard R. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (09) :3558-3565
[4]   STUDIES OF RUTAECARPINE AND RELATED QUINAZOLINOCARBOLINE ALKALOIDS [J].
BERGMAN, J ;
BERGMAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1246-1255
[5]   1-AMINOACYL-2,3-DIHYDRO-4(1H)-QUINAZOLINONE DERIVATIVES WITH CHOLERETIC AND ANTIFIBRILLATORY ACTIVITY [J].
BONOLA, G ;
DARE, P ;
MAGISTRE.MJ ;
MASSARAN.E ;
SETNIKAR, I .
JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (06) :1136-&
[6]   METAL CATALYSIS IN OXIDATION BY PEROXIDES .21. SULFIDE OXIDATION AND OLEFIN EPOXIDATION BY DILUTE HYDROGEN-PEROXIDE CATALYZED BY MOLYBDENUM AND TUNGSTEN DERIVATIVES UNDER PHASE-TRANSFER CONDITIONS [J].
BORTOLINI, O ;
DIFURIA, F ;
MODENA, G ;
SERAGLIA, R .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) :2688-2690
[7]   Molecular-docking-guided design, synthesis, and biologic evaluation of radioiodinated quinazolinone prodrugs [J].
Chen, Kai ;
Al Aowad, Ayman F. ;
Adelstein, S. James ;
Kassis, Amin I. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (04) :663-673
[8]   A microwave improvement in the synthesis of the quinazoline scaffold [J].
Chilin, Adriana ;
Marzaro, Giovanni ;
Zanatta, Samuele ;
Guiotto, Adriano .
TETRAHEDRON LETTERS, 2007, 48 (18) :3229-3231
[9]   One-pot neat reactions of carboxylic esters and alkylenediamines for efficient preparation of N-acylalkylenediamines [J].
Chou, WC ;
Tan, CW ;
Chen, SF ;
Ku, H .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :10015-10017
[10]   Synthesis of 2-aryl-1,2,3,4-tetrahydroquinazolin-1-ols and their conversion to 7-aryl-9H-6-oxa-5,8-diaza-benzocycloheptenes [J].
Coskun, N ;
Çetin, M .
TETRAHEDRON LETTERS, 2004, 45 (49) :8973-8975