Synthesis of selective SRPK-1 inhibitors: novel tricyclic quinoxaline derivatives.
作者： Zsolt Székelyhidi , János Pató , Frigyes Wáczek , Péter Bánhegyi , Bálint Hegymegi-Barakonyi
DOI: 10.1016/J.BMCL.2005.04.064
关键词: Tricyclic 、 Chemistry 、 Hepatitis B virus 、 Quinoxaline 、 Stereochemistry 、 Kinase
摘要: SR protein-specific kinase-1 (SRPK-1) has been identified as a validated target for hepatitis B virus (HBV). A series of novel tricyclic quinoxaline derivatives was designed and synthesised potential kinase inhibitory antiviral agents found to be active selective SRPK-1 kinase. Most these compounds have drug-like properties according experimentally determined LogP LogS values.
elsevier.com
sci-hub.se 参考文章(10)
Klára Valkó, Chris Bevan, Derek Reynolds, Chromatographic Hydrophobicity Index by Fast-Gradient RP-HPLC: A High-Throughput Alternative to log P/log D. Analytical Chemistry. ,vol. 69, pp. 2022- 2029 ,(1997) , 10.1021/AC961242D
Antonio Carta, Mario Loriga, Stefania Zanetti, Leonardo A Sechi, Quinoxalin-2-ones: Part 5. Synthesis and antimicrobial evaluation of 3-alkyl-, 3-halomethyl- and 3-carboxyethylquinoxaline-2-ones variously substituted on the benzo-moiety Farmaco. ,vol. 58, pp. 1251- 1255 ,(2003) , 10.1016/S0014-827X(03)00198-8
Stuart T. Hazeldine, Lisa Polin, Juiwanna Kushner, Jennifer Paluch, Kathryn White, Matthew Edelstein, Eduardo Palomino, Thomas H. Corbett, Jerome P. Horwitz, Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-(4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy)propionic acid (XK469). Journal of Medicinal Chemistry. ,vol. 44, pp. 1758- 1776 ,(2001) , 10.1021/JM0005149
D Eros, I Kovesdi, L Orfi, K Takacs-Novak, Gy Acsády, Gy Kéri, None, Reliability of logP predictions based on calculated molecular descriptors: a critical review. Current Medicinal Chemistry. ,vol. 9, pp. 1819- 1829 ,(2002) , 10.2174/0929867023369042
Aviv Gazit, Harald App, Gerald McMahon, Jefferey Chen, Alexander Levitzki, Frank D. Bohmer, Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins. Journal of Medicinal Chemistry. ,vol. 39, pp. 2170- 2177 ,(1996) , 10.1021/JM950727B
Matthew F Brown, Mike Avery, William H Brissette, J.H Chang, Kevin Colizza, Maryrose Conklyn, Amy P DiRico, Ronald P Gladue, John C Kath, Suzanne S Krueger, Paul D Lira, Brett M Lillie, Greg D Lundquist, Erin N Mairs, Eric B McElroy, Molly A McGlynn, Timothy J Paradis, Christopher S Poss, Michelle I Rossulek, Richard M Shepard, Jeff Sims, Timothy J Strelevitz, Susan Truesdell, Laurie A Tylaska, Kwansik Yoon, Deye Zheng, Novel CCR1 antagonists with improved metabolic stability Bioorganic & Medicinal Chemistry Letters. ,vol. 14, pp. 2175- 2179 ,(2004) , 10.1016/J.BMCL.2004.02.022
Daniel Eros, Gyorgy Keri, Istvan Kovesdi, Csaba Szantai-Kis, Gyorgy Meszaros, Laszlo Orfi, Comparison of predictive ability of water solubility QSPR models generated by MLR, PLS and ANN methods Mini-reviews in Medicinal Chemistry. ,vol. 4, pp. 167- 177 ,(2004) , 10.2174/1389557043487466
Henrik Daub, Stephanie Blencke, Peter Habenberger, Alexander Kurtenbach, Julia Dennenmoser, Josef Wissing, Axel Ullrich, Matt Cotten, Identification of SRPK1 and SRPK2 as the Major Cellular Protein Kinases Phosphorylating Hepatitis B Virus Core Protein Journal of Virology. ,vol. 76, pp. 8124- 8137 ,(2002) , 10.1128/JVI.76.16.8124-8137.2002
Wei He, Michael R. Myers, Barbara Hanney, Alfred P. Spada, Glenda Bilder, Helen Galzcinski, Dilip Amin, Saul Needle, Ken Page, Zaid Jayyosi, Mark H. Perrone, Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 2: the synthesis and biological activities of RPR127963 an orally bioavailable inhibitor. Bioorganic & Medicinal Chemistry Letters. ,vol. 13, pp. 3097- 3100 ,(2003) , 10.1016/S0960-894X(03)00655-3
Michael R. Myers, Wei He, Barbara Hanney, Natalie Setzer, Martin P. Maguire, Allison Zulli, Glenda Bilder, Helen Galzcinski, Dilip Amin, Saul Needle, Alfred P. Spada, Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 1: SAR exploration and effective bioisosteric replacement of a phenyl substituent. Bioorganic & Medicinal Chemistry Letters. ,vol. 13, pp. 3091- 3095 ,(2003) , 10.1016/S0960-894X(03)00654-1