Synthesis and bioactivity of 4-alkyl(aryl)thioquinazoline derivatives

被引：45

作者：

Yang, Song ^{[1
]}

Li, Zhi ^{[1
]}

Jin, Linhong ^{[1
]}

Song, Baoan ^{[1
]}

Liu, Gang ^{[1
]}

Chen, Jiang ^{[1
]}

Chen, Zhuo ^{[1
]}

Hu, Deyu ^{[1
]}

Xue, Wei ^{[1
]}

Xu, Ruiqing ^{[1
]}

机构：

[1] Guizhou Univ, Minist Educ, Ctr Res & Dev Fine Chem, Key Lab Green Pesticide & Bioengn, Guiyang 550025, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 08期

基金：

中国国家自然科学基金;

关键词：

quinazoline; thioether; synthesis; anti-cancer activity; against ERK phosphorylation;

D O I：

10.1016/j.bmcl.2007.01.101

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Some S'-substituted 4-alkyl(aryl)thioquinazoline derivatives were synthesized through thioetherification reaction of 4-chloroquinazolines 2 and thiol compounds 1 refluxed in acetone in the presence of K2CO3. Their structures were verified by elemental analysis, IR, H-1 NMR, and C-13 NMR. The compounds were evaluated for their anti-proliferative activities against some cancer cells in vitro by MTT method. Among them, 3c, 3a, 3d, 3f, and 31 were highly effective against PC3 cells and 3a-3m showed weak activities against Bcap37 and BGC823 cells. The IC50 value of 3c, 3a, 3d, 3f, and 31 against PC3 cell was 1.8, 5.6, 8.1, 8.7, and 8.9 mu M, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2193 / 2196

页数：4

共 15 条

[1]

Abdel Hamid S.G., 2001, SCI PHARM, V69, P351

[2]

Egger Denise, 1994, Molecular Biotechnology, V1, P289, DOI 10.1007/BF02921696

[3] Synthesis, structure, and bioactivity of N′-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives [J].

Jin, Linhong ;

Chen, Jiang ;

Song, Baoan ;

Chen, Zhuo ;

Yang, Song ;

Li, Qianzhu ;

Hu, Deyu ;

Xu, Ruiqing .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) :5036-5040

[4]

Kersemaekers AMF, 1999, CLIN CANCER RES, V5, P577

[5]

Klohs Wayne D., 1997, Current Opinion in Oncology, V9, P562, DOI 10.1097/00001622-199711000-00012

[6] Prognostic significance of epidermal growth factor receptor in laryngeal squamous cell carcinoma [J].

Maurizi, M ;

Almadori, G ;

Ferrandina, G ;

Distefano, M ;

Romanini, ME ;

Cadoni, G ;

BenedettiPanici, P ;

Paludetti, G ;

Scambia, G ;

Mancuso, S .

BRITISH JOURNAL OF CANCER, 1996, 74 (08) :1253-1257

[7]

Rádl S, 2000, ARCH PHARM, V333, P381, DOI 10.1002/1521-4184(200011)333:11<381::AID-ARDP381>3.0.CO

[8]

2-A

[9] NEW COLORIMETRIC CYTOTOXICITY ASSAY FOR ANTICANCER-DRUG SCREENING [J].

SKEHAN, P ;

STORENG, R ;

SCUDIERO, D ;

MONKS, A ;

MCMAHON, J ;

VISTICA, D ;

WARREN, JT ;

BOKESCH, H ;

KENNEY, S ;

BOYD, MR .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1990, 82 (13) :1107-1112

[10] Tyrosine kinase inhibitors.: 15.: 4-(phenylamino)quinazoline and 4-(phenylamino)pyrido[d] pyrimidine acrylamides as irreversible inhibitors of the ATP binding site of the epidermal growth factor receptor [J].

Smaill, JB ;

Palmer, BD ;

Rewcastle, GW ;

Denny, WA ;

McNamara, DJ ;

Dobrusin, EM ;

Bridges, AJ ;

Zhou, HR ;

Showalter, HDH ;

Winters, RT ;

Leopold, WR ;

Fry, DW ;

Nelson, JM ;

Slintak, V ;

Elliot, WL ;

Roberts, BJ ;

Vincent, PW ;

Patmore, SJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (10) :1803-1815

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