Synthesis of isoquinolinone-based tricycles as novel poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors

被引:32
作者
Chen, Jianyang [1 ]
Peng, Haixia [1 ]
He, Jinxue [2 ]
Huan, Xiajuan [2 ]
Miao, Zehong [2 ]
Yang, Chunhao [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Dept Med Chem, Shanghai 201203, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Div Antitumor Pharmacol, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
Isoquinolinone-based tricycles; PARP-1; inhibitors; Antitumor; CANCER; REPAIR; CELLS; THERAPY; DESIGN;
D O I
10.1016/j.bmcl.2014.04.061
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The isoquinolinone-based tricyclic compounds were designed and synthesized. Preliminary biological study of these compounds provided potent compounds 17a, 33b, 33c, 33d, and 33g with low nanomolar IC(50)s against PARP-1 enzyme. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2669 / 2673
页数:5
相关论文
共 17 条
[1]   INHIBITORS AND ACTIVATORS OF ADP-RIBOSYLATION REACTIONS [J].
BANASIK, M ;
UEDA, K .
MOLECULAR AND CELLULAR BIOCHEMISTRY, 1994, 138 (1-2) :185-197
[2]   Base excision repair is impaired in mammalian cells lacking poly(ADP-ribose) polymerase-1 [J].
Dantzer, F ;
de la Rubia, G ;
Murcia, JMD ;
Hostomsky, Z ;
de Murcia, G ;
Schreiber, V .
BIOCHEMISTRY, 2000, 39 (25) :7559-7569
[3]   Requirement of poly(ADP-ribose) polymerase in recovery from DNA damage in mice and in cells [J].
deMurcia, JM ;
Niedergang, C ;
Trucco, C ;
Ricoul, M ;
Dutrillaux, B ;
Mark, M ;
Oliver, FJ ;
Masson, M ;
Dierich, A ;
LeMeur, M ;
Walztinger, C ;
Chambon, P ;
deMurcia, G .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (14) :7303-7307
[4]   Evolution of Poly(ADP-ribose) Polymerase-1 (PARP-1) Inhibitors. From Concept to Clinic [J].
Ferraris, Dana V. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (12) :4561-4584
[5]   DNA repair pathways as targets for cancer therapy [J].
Helleday, Thomas ;
Petermann, Eva ;
Lundin, Cecilia ;
Hodgson, Ben ;
Sharma, Ricky A. .
NATURE REVIEWS CANCER, 2008, 8 (03) :193-204
[6]   Poly(ADP-ribose) polymerase as a drug target for cardiovascular disease and cancer:: An update [J].
Horvath, Eszter M. ;
Szabo, Csaba .
DRUG NEWS & PERSPECTIVES, 2007, 20 (03) :171-181
[7]   Discovery of 2-{4-[(3S)-Piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827): A Novel Oral Poly(ADP-ribose)polymerase (PARP) Inhibitor Efficacious in BRCA-1 and-2 Mutant Tumors [J].
Jones, Philip ;
Altamura, Sergio ;
Boueres, Julia ;
Ferrigno, Federica ;
Fonsi, Massimiliano ;
Giomini, Claudia ;
Lamartina, Stefania ;
Monteagudo, Edith ;
Ontoria, Jesus M. ;
Orsale, Maria Vittoria ;
Palumbi, Maria Cecilia ;
Pesci, Silvia ;
Roscilli, Giuseppe ;
Scarpelli, Rita ;
Schultz-Fademrecht, Carsten ;
Toniatti, Carlo ;
Rowley, Michael .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (22) :7170-7185
[8]   Novel tricyclic poly(ADP-ribose) polymerase-1 inhibitors with potent anticancer chemopotentiating activity: Design, synthesis, and X-ray cocrystal structure [J].
Koch, SSC ;
Thoresen, LH ;
Tikhe, JG ;
Maegley, KA ;
Almassy, RJ ;
Li, JK ;
Yu, XH ;
Zook, SE ;
Kumpf, RA ;
Zhang, C ;
Boritzki, TJ ;
Mansour, RN ;
Zhang, KE ;
Ekker, A ;
Calabrese, CR ;
Curtin, NJ ;
Kyle, S ;
Thomas, HD ;
Wang, LZ ;
Calvert, AH ;
Golding, BT ;
Griffin, RJ ;
Newell, DR ;
Webber, SE ;
Hostomsky, Z .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (23) :4961-4974
[9]   Synthesis of substituted 5[H]phenanthridin-6-ones as potent poly(ADP-ribose)polymerase-1 (PARP1) inhibitors [J].
Li, JH ;
Serdyuk, L ;
Ferraris, DV ;
Xiao, G ;
Tays, KL ;
Kletzly, PW ;
Li, WX ;
Lautar, S ;
Zhang, J ;
Kalish, VJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1687-1690
[10]   Targeted therapy for cancer using PARP inhibitors [J].
Lord, Christopher J. ;
Ashworth, Alan .
CURRENT OPINION IN PHARMACOLOGY, 2008, 8 (04) :363-369