Synthesis, analgesic and anti-inflammatory evaluation of some new 3H-quinazolin-4-one derivatives

被引:50
作者
Alafeefy, Ahmed M. [1 ]
Kadi, Adnan A. [1 ]
El-Azab, Adel S. [1 ]
Abdel-Hamide, Sami G. [1 ,2 ]
Daba, Mohamad-Hesham Y. [2 ]
机构
[1] King Saud Univ, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
[2] King Saud Univ, Coll Pharm, Dept Clin Pharm, Riyadh 11451, Saudi Arabia
关键词
analgesic; anti-inflammatory; COX-inhibitors; oxadiazole; 3H-quinazolin-4-one;
D O I
10.1002/ardp.200700271
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In this study, we have synthesized a series of 3H-quinazolin-4-ones in order to obtain new compounds with potential analgesic and anti-inflammatory activity. The structures of the newly synthesized compounds were confirmed by means of infrared, nuclear magnetic resonance and mass spectroscopy. Some compounds were evaluated for their analgesic and anti-inflammatory activities by writhing and carrageenan-induced rat paw edema tests, respectively. In comparison to the standard drug indomethacine, compounds 4, 6c, 12-14, 16, 18, 19, and 22 induced significant reduction in the writhing response while compounds 6c, 12, 14, 16, 18, and 22 produced a good dose-dependent anti-inflammatory activity. The best dual analgesic / anti-inflammatory relative activity was observed with compounds 6c,14,16, 18, and 22.
引用
收藏
页码:377 / 385
页数:9
相关论文
共 21 条
[1]  
ADEEB OA, 2006, ARZNEIMFORSCHUNG DRU, V56, P40
[2]   1,3,4-thiadiazoles.: Regioselective O-demethylation on dehydrative cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides with sulphuric acid [J].
Al-Omar, M ;
Al-Deeb, OA ;
Al-Khamees, HA ;
El-Emam, AA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (12) :2509-2517
[3]   Synthesis and pharmacological evaluation of some 3-(4-methoxyphenyl)-2-substitutedamino-quinazolin-4(3H)-ones as analgesic and anti-inflammatory agents [J].
Alagarsamy, Veerachamy ;
Murugesan, Sankaranarayanan .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2007, 55 (01) :76-80
[4]  
Bekhit AA, 1998, PHARMAZIE, V53, P539
[5]   Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(I-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones [J].
El-Emam, AA ;
Al-Deeb, OA ;
Al-Omar, M ;
Lehmann, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (19) :5107-5113
[6]  
ELEMAM AA, 1991, ARZNEIMITTELFORSCH, V41-2, P1260
[7]   Prostaglandins and the mechanism of analgesia produced by aspirin-like drugs (Reprinted from Brit J Pharmacol, vol 49, pg 86-97, 1973) [J].
Ferreira, SH ;
Moncada, S ;
Vane, JR .
BRITISH JOURNAL OF PHARMACOLOGY, 1997, 120 (04) :401-412
[8]  
Georgiev V. S., 1985, US Patent, Patent No. [4,549,014, 4549014]
[9]   Signaling events involved in cytokine and chemokine production induced by secretory phospholipase A2 in human lung macrophages [J].
Granata, Francescopaolo ;
Frattini, Annunziata ;
Loffredo, Stefania ;
Del Prete, Annalisa ;
Sozzani, Silvano ;
Marone, Gianni ;
Triggiani, Massimo .
EUROPEAN JOURNAL OF IMMUNOLOGY, 2006, 36 (07) :1938-1950
[10]   SYNTHESIS AND BIOLOGICAL EVALUATION OF 2-STYRYLQUINAZOLIN-4(3H)-ONES, A NEW CLASS OF ANTIMITOTIC ANTICANCER AGENTS WHICH INHIBIT TUBULIN POLYMERIZATION [J].
JIANG, JB ;
HESSON, DP ;
DUSAK, BA ;
DEXTER, DL ;
KANG, GJ ;
HAMEL, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1721-1728