Design, synthesis and biological evaluation of novel indano- and thiaindano-pyrazoles with potential interest for Alzheimer's disease

被引:25
作者
Genest, David [1 ,2 ]
Rochais, Christophe [1 ,2 ]
Lecoutey, Cedric [1 ,2 ]
Santos, Jana Sopkova-de Oliveira [1 ,2 ]
Ballandonne, Celine [1 ,2 ]
Butt-Gueulle, Sabrina [1 ,2 ]
Legay, Remi [1 ,2 ]
Since, Marc [1 ,2 ]
Dallemagne, Patrick [1 ,2 ]
机构
[1] Normandie Univ, Caen, France
[2] Univ Caen Basse Normandie, Ctr Etud & Rech Med Normandie, EA FR CNRS SF ICORE INC3M 4258 3038 4206, UFR Sci Pharmaceut, F-14032 Caen, France
关键词
SITE ACETYLCHOLINESTERASE INHIBITORS; TARGET-DIRECTED LIGANDS; GENETIC ALGORITHM; MODIFYING AGENTS; ACHE INHIBITORS; DUAL INHIBITORS; PERIPHERAL SITE; AMMONIUM-SALTS; HIGHLY POTENT; DERIVATIVES;
D O I
10.1039/c3md00041a
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
The synthesis of eighteen novel (thia)indanopyrazole derivatives was achieved starting from amino(thia)indanones. Some of them displayed a dual binding site acetylcholinesterase inhibition which makes them potentially interesting for Alzheimer's disease treatment.
引用
收藏
页码:925 / 931
页数:7
相关论文
共 43 条
[1]   β-amyloid aggregation induced by human acetylcholinesterase:: inhibition studies [J].
Bartolini, M ;
Bertucci, C ;
Cavrini, V ;
Andrisano, V .
BIOCHEMICAL PHARMACOLOGY, 2003, 65 (03) :407-416
[2]   THE CHOLINERGIC HYPOTHESIS OF GERIATRIC MEMORY DYSFUNCTION [J].
BARTUS, RT ;
DEAN, RL ;
BEER, B ;
LIPPA, AS .
SCIENCE, 1982, 217 (4558) :408-417
[3]   Novel B-ring modified allocolchicinoids of the NCME series:: Design, synthesis, antimicrotubule activity and cytotoxicity [J].
Bergemann, S ;
Brecht, R ;
Büttner, F ;
Guénard, D ;
Gust, R ;
Seitz, G ;
Stubbs, MT ;
Thoret, S .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) :1269-1281
[4]   Identification of 4,5-Dihydro-1H-pyrazolo[4,3-h]quinazoline Derivatives as a New Class of Orally and Selective Polo-Like Kinase 1 Inhibitors [J].
Beria, Italo ;
Ballinari, Dario ;
Bertrand, Jay Aaron ;
Borghi, Daniela ;
Bossi, Roberto Tiberio ;
Brasca, Maria Gabriella ;
Cappella, Paolo ;
Caruso, Michele ;
Ceccarelli, Walter ;
Ciavolella, Antonella ;
Cristiani, Cinzia ;
Croci, Valter ;
De Ponti, Anna ;
Fachin, Gabriele ;
Ferguson, Ronald Dale ;
Lansen, Jacqueline ;
Moll, Jurgen Karl ;
Pesenti, Enrico ;
Posteri, Helena ;
Perego, Rita ;
Rocchetti, Maurizio ;
Storici, Paola ;
Volpi, Daniele ;
Valsasina, Barbara .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (09) :3532-3551
[5]   Multi-target-directed drug design strategy: From a dual binding site acetylcholinesterase inhibitor to a trifunctional compound against Alzheimer's disease [J].
Bolognesi, Maria Laura ;
Cavalli, Andrea ;
Valgimigli, Luca ;
Bartolini, Manuela ;
Rosini, Michela ;
Andrisano, Vincenza ;
Recanatini, Maurizio ;
Melchiorre, Carlo .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (26) :6446-6449
[6]   Novel class of quinone-bearing polyamines as multi-target-directed ligands to combat Alzheimer's disease [J].
Bolognesi, Maria Laura ;
Banzi, Rita ;
Bartolini, Manuela ;
Cavalli, Andrea ;
Tarozzi, Andrea ;
Andrisano, Vincenza ;
Minarini, Anna ;
Rosini, Michela ;
Tumiatti, Vincenzo ;
Bergamini, Christian ;
Fato, Romana ;
Lenaz, Giorgio ;
Hrelia, Patrizia ;
Cattaneo, Antonino ;
Recanatini, Maurizio ;
Melchiorre, Carlo .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (20) :4882-4897
[7]   Progress in acetylcholinesterase inhibitors for Alzheimer's disease [J].
Bolognesi, Maria Laura ;
Minarini, Anna ;
Tumiatti, Vincenzo ;
Melchiorre, Carlo .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2006, 16 (06) :811-823
[8]   Multitargeted drugs discovery: Balancing anti-amyloid and anticholinesterase capacity in a single chemical entity [J].
Bolognesi, Maria Laura ;
Bartolini, Manuela ;
Tarozzi, Andrea ;
Morroni, Fabiana ;
Lizzi, Federica ;
Milelli, Andrea ;
Minarini, Anna ;
Rosini, Michela ;
Hrelia, Patrizia ;
Andrisano, Vincenza ;
Melchiorre, Carlo .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (09) :2655-2658
[9]   Propidium-based polyamine ligands as potent inhibitors of acetylcholinesterase and acetylcholinesterase-induced amyloid-β aggregation [J].
Bolognesi, ML ;
Andrisano, V ;
Bartolini, M ;
Banzi, R ;
Melchiorre, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (01) :24-27
[10]   ACID AMIDE-REACTIONS L - ORTHO-AMIDES .I. SYNTHESIS AND PROPERTIES OF AMIDE ACETALES AND AMINALESTERS [J].
BREDERECK, H ;
SIMCHEN, G ;
REBSDAT, S ;
KANTLEHNER, W ;
HORN, P ;
WAHL, R ;
HOFFMANN, H ;
GRIESHABER, P .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (01) :41-+