Solution-phase parallel synthesis of a library of Δ2-pyrazolines

被引：21
作者：
Manyem, Shankar
Sibi, Mukund P. [1 ]
Lushington, Gerald H.
Neuenswander, Benjamin
Schoenen, Frank
Aube, Jeffrey
机构：
[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA
[2] Univ Kansas, Ctr Excellence Chem Methodol & Lib Dev, Lawrence, KS 66047 USA
来源：
JOURNAL OF COMBINATORIAL CHEMISTRY | 2007年 / 9卷 / 01期
关键词：
D O I：
10.1021/cc0601175
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A parallel synthesis of a library (80 members) of 2-pyrazolines in solution phase is described. The 2-pyrazoline core was accessed through the [3 + 2] cycloaddition of nitrilimines with enoyl oxazolidinones. The cycloaddition provided two regioisomers, the major product being the C regioisomer. The oxazolidinone moiety was further reduced to the primary alcohol, producing another library of 5-hydroxymethyl-2-pyrazolines. The Lipinski profiles and calculated ADME properties of the compounds are also reported.
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页码：20 / 28
页数：9
相关论文
共 37 条
[1]   Methodologies for generating solution-phase combinatorial libraries [J].
An, HY ;
Cook, PD .
CHEMICAL REVIEWS, 2000, 100 (09) :3311-3340
[2]   Parallel solution phase synthesis of N-substituted 2-pyrazoline libraries [J].
Bauer, U ;
Egner, BJ ;
Nilsson, I ;
Berghult, M .
TETRAHEDRON LETTERS, 2000, 41 (15) :2713-2717
[3]   Inhibition of nNOS activity in rat brain by synthetic kynurenines:: Structure-activity dependence [J].
Camacho, E ;
León, J ;
Carrión, A ;
Entrena, A ;
Escames, G ;
Khaldy, H ;
Acuña-Castroviejo, D ;
Gallo, MA ;
Espinosa, A .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (02) :263-274
[4]   4,5-Dihydro-1H-pyrazole derivatives with inhibitory nNOS activity in rat brain:: Synthesis and structure-activity relationships [J].
Camacho, ME ;
León, J ;
Entrena, A ;
Velasco, G ;
Carrión, MD ;
Escames, G ;
Vivó, A ;
Acuña-Castroviejo, D ;
Gallo, MA ;
Espinosa, A .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (23) :5641-5650
[5]   Synthesis and iNOS/nNOS inhibitory activities of new benzoylpyrazoline derivatives [J].
Carrión, MD ;
Camacho, ME ;
León, J ;
Escames, G ;
Tapias, V ;
Acuña-Castroviejo, D ;
Gallo, MA ;
Espinosa, A .
TETRAHEDRON, 2004, 60 (18) :4051-4069
[6]   Magnesium perchlorate as an efficient catalyst for the synthesis of imines and phenylhydrazones [J].
Chakraborti, AK ;
Bhagat, S ;
Rudrawar, S .
TETRAHEDRON LETTERS, 2004, 45 (41) :7641-7644
[7]   Synthesis and in vitro selective anti-Helicobacter pylori activity of pyrazoline derivatives [J].
Chimenti, F ;
Bizzarri, B ;
Manna, F ;
Bolasco, A ;
Secci, D ;
Chimenti, P ;
Granese, A ;
Rivanera, D ;
Lilli, D ;
Scaltrito, MM ;
Brenciaglia, MI .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :603-607
[8]   Synthesis and selective inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives against monoamine oxidase [J].
Chimenti, F ;
Bolasco, A ;
Manna, F ;
Secci, D ;
Chimenti, P ;
Befani, O ;
Turini, P ;
Giovannini, V ;
Mondovì, B ;
Cirilli, R ;
La Torre, F .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (08) :2071-2074
[9]   Kinesin spindle protein (KSP) inhibitors. Part 4: Structure-based design of 5-alkylamino-3,5-diaryl-4,5-dihydropyrazoles as potent, water-soluble inhibitors of the mitotic kinesin KSP [J].
Cox, CD ;
Torrent, M ;
Breslin, MJ ;
Mariano, BJ ;
Whitman, DB ;
Coleman, PJ ;
Buser, CA ;
Walsh, ES ;
Hamilton, K ;
Schaber, MD ;
Lobell, RB ;
Tao, WK ;
South, VJ ;
Kohl, NE ;
Yan, YW ;
Kuo, LC ;
Prueksaritanont, T ;
Slaughter, DE ;
Li, CZ ;
Mahan, E ;
Lu, B ;
Hartman, GD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (12) :3175-3179
[10]   Kinesin spindle protein (KSP) inhibitors. Part 1: The discovery of 3,5-diaryl-4,5-dihydropyrazoles as potent and selective inhibitors of the mitotic kinesin KSP [J].
Cox, CD ;
Breslin, MJ ;
Brenda, JM ;
Coleman, PJ ;
Buser, CA ;
Walsh, ES ;
Hamilton, K ;
Huber, HE ;
Kohl, NE ;
Torrent, M ;
Yan, YW ;
Kuo, LC ;
Hartman, GD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (08) :2041-2045
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