Synthesis of 4-Substituted 2-(4-Methylpiperazino)pyrimidines and Quinazoline Analogs as Serotonin 5-HT2A Receptor Ligands
作者： Jaroslaw Saczewski , Aldona Paluchowska , Jeffrey Klenc , Elizabeth Raux , Samuel Barnes
DOI: 10.1002/JHET.236
关键词:
摘要: The addition reaction of lithium reagents to the 4 position 2-chloropyrimidine or 2-chloroquinazoline followed by oxidation resultant dihydro intermediate product is a powerful tool for synthesis 4-substituted 2-chloropyrimidines 2-chloroquinazolines. 4-Vinyl derivatives undergo conjugate nucleophilic across vinyl group. A displacement chloride in 4substituted 2-chloroquinazolines treatment with 4-methylpiperazine provides compounds that are antagonists serotonin 5-HT2A receptor.
sci-hub.se 参考文章(22)
Thomas Kauffmann, From the Principle of Areno-Analogy to Heterocyclopolyaromatic Compounds Angewandte Chemie International Edition in English. ,vol. 18, pp. 1- 19 ,(1979) , 10.1002/ANIE.197900013
Maria J. Mokrosz, Beata Duszyńska, Aleksandra Klodzińska, Anna Dereń-Wesolek, Ewa Chojnacka-Wójcik, Timothy C. Baranowski, Ibrahim M. Abdou, Naomi P. Redmore, Lucjan Strekowski, 4-(3-furyl)-2-(4-methylpiperazino)pyrimidines: Potent 5-HT2A receptor antagonists Bioorganic & Medicinal Chemistry Letters. ,vol. 7, pp. 1635- 1638 ,(1997) , 10.1016/S0960-894X(97)00291-6
Lucjan Strekowski, Jerzy L. Mokrosz, W. David Wilson, Maria J. Mokrosz, Alewtina Strekowski, Stereoelectronic factors in the interaction with DNA of small aromatic molecules substituted with a short cationic chain : importance of the polarity of the aromatic system of the molecule Biochemistry. ,vol. 31, pp. 10802- 10808 ,(1992) , 10.1021/BI00159A022
Jean-Paul Quintard, Bernard Elissondo, Michel Pereyre, New organotin synthons providing α-alkoxyorganolithium reagents Journal of Organometallic Chemistry. ,vol. 212, ,(1981) , 10.1016/S0022-328X(00)85670-3
Paul A. Bartlett, James D. Meadows, Eckhard Ottow, Enantiodivergent syntheses of (+)- and (−)-nonactic acid and the total synthesis of nonactin Journal of the American Chemical Society. ,vol. 106, pp. 5304- 5311 ,(1984) , 10.1021/JA00330A045
Lucjan Strekowski, W. David Wilson, Jerzy L. Mokrosz, Maria J. Mokrosz, Donald B. Harden, Farial A. Tanious, Roman L. Wydra, Sidney A. Crow, Quantitative structure-activity relationship analysis of cation-substituted polyaromatic compounds as potentiators (amplifiers) of bleomycin-mediated degradation of DNA. Journal of Medicinal Chemistry. ,vol. 34, pp. 580- 588 ,(1991) , 10.1021/JM00106A017
JL Mokrosz, B Duszyńska, S Charakchieva-Minol, AJ Bojarski, MJ Mokrosz, RL Wydra, L Janda, L Strekowski, Structure-activity relationship studies of CNS agents. Part 29. N-Methylpiperazino-substituted derivatives of quinazoline, phthalazine and quinoline as novel α1, 5-HT1A and 5-HT2A receptor ligands European Journal of Medicinal Chemistry. ,vol. 31, pp. 973- 980 ,(1996) , 10.1016/S0223-5234(97)86176-4
W. David Wilson, Farial A. Tanious, Shaikh Mizan, Shijie Yao, Alexander S. Kiselyov, Gerald Zon, Lucjan Strekowski, DNA triple-helix specific intercalators as antigene enhancers : unfused aromatic cations Biochemistry. ,vol. 32, pp. 10614- 10621 ,(1993) , 10.1021/BI00091A011
Maria J. Mokrosz, Lucjan Strekowski, Wei Xing Kozak, Beata Duszyńska, Andrzej J. Bojarski, Aleksandra Kłodzinska, Agnieszka Czarny, Marek T. Cegła, Anna Dereń-Wesołek, Ewa Chojnacka-Wójcik, Stefan Dove, Jerzy L. Mokrosz, Structure-Activity Relationship Studies of CNS Agents, Part 25: 4,6-Di(heteroaryl)-2-(N-methylpiperazino)pyrimidines as New, Potent 5-HT2A Receptor Ligands: A Verification of the Topographic Model Archiv der Pharmazie. ,vol. 328, pp. 659- 666 ,(1995) , 10.1002/ARDP.19953280906
W. David Wilson, Farial A. Tanious, Rebecca A. Watson, Henryk J. Barton, Alewtina Strekowska, Donald B. Harden, Lucjan Strekowski, Interaction of unfused tricyclic aromatic cations with DNA: a new class of intercalators. Biochemistry. ,vol. 28, pp. 1984- 1992 ,(1989) , 10.1021/BI00431A005