Structure-activity relationship studies of a new series of imidazo[2,1-f] purinones as potent and selective A3 adenosine receptor antagonists

被引：14

作者：

Baraldi, Pier Giovanni ^{[1
]}

Preti, Delia ^{[1
]}

Tabrizi, Mojgan Aghazadeh ^{[1
]}

Romagnoli, Romeo ^{[1
]}

Saponaro, Giulia ^{[1
]}

Baraldi, Stefania ^{[1
]}

Botta, Maurizio ^{[3
]}

Bernardini, Cesare ^{[3
]}

Tafi, Andrea ^{[3
]}

Tuccinardi, Tiziano ^{[4
]}

Martinelli, Adriano ^{[4
]}

Varani, Katia ^{[2
]}

Borea, Pier Andrea ^{[2
]}

机构：

[1] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy

[2] Univ Ferrara, Dipartimento Med Clin & Sperimentale, Sez Farmacol, I-44100 Ferrara, Italy

[3] Univ Siena, Dipartimento Farm Chim Tecnol, I-53100 Siena, Italy

[4] Univ Pisa, Dipartimento Sci Farmaceut, I-56126 Pisa, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2008年 / 16卷 / 24期

关键词：

Adenosine; Cancer; A(3) antagonists; Imidazo[2,1-f]purinones; Docking; 3D-QSAR;

D O I：

10.1016/j.bmc.2008.10.049

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We recently described the synthesis of 1-benzyl-3-propyl-1H,8H-imidazo[2,1-f]purine-2,4-diones, new potent and selective A(3) adenosine receptor antagonists containing a xanthine core. The present work can be considered an extension of our SAR studies on related structures in which the effect of different kind of substitutions at the 1-, 3- and 8-positions has been evaluated in order to improve both the potency and the hydrophilicity of the originally synthesised molecules. The A(3) binding disposition of these compounds was also investigated through docking and 3D-QSAR studies. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10281 / 10294

页数：14

共 66 条

[1]

Avila MY, 2002, INVEST OPHTH VIS SCI, V43, P3021

[2]

Baharav E, 2005, J RHEUMATOL, V32, P469

[3]

Baraldi PG, 2000, MED RES REV, V20, P103, DOI 10.1002/(SICI)1098-1128(200003)20:2<103::AID-MED1>3.0.CO

[4]

2-X

[5] New 2-arylpyrazolo[4,3-c]quinoline derivatives as potent and selective human A3 adenosine receptor antagonists [J].

Baraldi, PG ;

Tabrizi, MA ;

Preti, D ;

Bovero, A ;

Fruttarolo, F ;

Romagnoli, R ;

Zaid, NA ;

Moorman, AR ;

Varani, K ;

Borea, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :5001-5008

[6] New pyrrolo[2,1-f]purine-2,4-dione and imidazo[2,1-f]purine-2,4-dione derivatives as potent and selective human A3 adenosine receptor antagonists [J].

Baraldi, PG ;

Preti, D ;

Tabrizi, MA ;

Fruttarolo, F ;

Romagnoli, R ;

Zaid, NA ;

Moorman, AR ;

Merighi, S ;

Varani, K ;

Borea, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (14) :4697-4701

[7] Recent developments in the field of A3 adenosine receptor antagonists [J].

Baraldi, PG ;

Tabrizi, MA ;

Fruttarolo, F ;

Bovero, A ;

Avitabile, B ;

Preti, D ;

Romagnoli, R ;

Merighi, S ;

Gessi, S ;

Varani, K ;

Borea, PA .

DRUG DEVELOPMENT RESEARCH, 2003, 58 (04) :315-329

[8]

Baraldi PG, 2001, SYNTHESIS-STUTTGART, P773

[9] New potent and selective human adenosine A3 receptor antagonists [J].

Baraldi, PG ;

Borea, PA .

TRENDS IN PHARMACOLOGICAL SCIENCES, 2000, 21 (12) :456-459

[10] Binding thermodynamics at A(1) and A(2A) adenosine receptors [J].

Borea, PA ;

Dalpiaz, A ;

Varani, K ;

Gessi, S ;

Gilli, G .

LIFE SCIENCES, 1996, 59 (17) :1373-1388

← 1 2 3 4 5 6 7 →