Efficient Multicomponent Reaction Synthesis of the Schistosomiasis Drug Praziquantel

被引:84
作者
Cao, Haiping [1 ]
Liu, Haixia [1 ]
Doemling, Alexander [1 ]
机构
[1] Univ Pittsburgh, Dept Pharmaceut Sci & Chem, Pittsburgh, PA 15261 USA
关键词
drug discovery; isocyanides; multicomponent reactions; Pictet-Spengler reaction; Ugi reaction; GENITAL SCHISTOSOMIASIS; ASSOCIATION; HIV;
D O I
10.1002/chem.201002046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Shorter than ever: A convergent, efficient, and scalable access based on a key Ugi four-component reaction (4CR) followed by a Pictet-Spengler reaction comprises the shortest known synthesis to the schistosomiasis drug praziquantel (see scheme). © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12296 / 12298
页数:3
相关论文
共 31 条
[1]   An unusual association: vulval schistosomiasis, microinvasive vulval squamous cell carcinoma and high-grade vulval intraepithelial neoplasia in HIV patient [J].
Alalade, A. O. ;
Leeson, S. C. ;
Andrady, U. .
GYNECOLOGICAL SURGERY, 2009, 6 (02) :177-179
[2]  
[Anonymous], ANGEW CHEM
[3]   AN INTERNAL IMINO-DIELS-ALDER ROUTE TO A TETRAHYDROISOQUINOLINE [J].
BERKOWITZ, WF ;
JOHN, TV .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5269-5271
[4]  
Bilharz T, 1856, WIEN MED WOCHENSCHR, V6, P49
[5]  
Bilharz T. M., 1856, WIEN MED WOCHENSCHR, V6, P65
[6]  
BILHARZ TM, 1858, Z KAIS KGL GES ARZTE, V14, P447
[7]   Chemotherapy of schistosomiasis: present and future [J].
Caffrey, Conor R. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2007, 11 (04) :433-439
[8]   Acute Schistosoma mansoni Infection Increases Susceptibility to Systemic SHIV Clade C Infection in Rhesus Macaques after Mucosal Virus Exposure [J].
Chenine, Agnes-Laurence ;
Shai-Kobiler, Ela ;
Steele, Lisa N. ;
Ong, Helena ;
Augostini, Peter ;
Song, Ruijiang ;
Lee, Sandra J. ;
Autissier, Patrick ;
Ruprecht, Ruth M. ;
Secor, W. Evan .
PLOS NEGLECTED TROPICAL DISEASES, 2008, 2 (07)
[9]   FEMALE GENITAL SCHISTOSOMIASIS AS A RISK-FACTOR FOR THE TRANSMISSION OF HIV [J].
FELDMEIER, H ;
KRANTZ, I ;
POGGENSEE, G .
INTERNATIONAL JOURNAL OF STD & AIDS, 1994, 5 (05) :368-372
[10]   Synthesis, Biological Evaluation, and Molecular Docking of Ugi Products Containing a Zinc-Chelating Moiety as Novel Inhibitors of Histone Deacetylases [J].
Grolla, Ambra A. ;
Podesta, Valeria ;
Chini, Maria Giovanna ;
Di Micco, Simone ;
Vallario, Antonella ;
Genazzani, Armando A. ;
Canonico, Pier Luigi ;
Bifulco, Giuseppe ;
Tron, Gian Cesare ;
Sorba, Giovanni ;
Pirali, Tracey .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) :2776-2785