Pharmacological Importance of Optically Active Tetrahydro-β-carbolines and Synthetic Approaches to Create the C1 Stereocenter

作者: Aino Laine , Christopher Lood , Ari Koskinen

DOI: 10.3390/MOLECULES19021544

关键词:

摘要: 1,2,3,4-Tetrahydro-β-carbolines (THβCs) are a pharmacologically important group of compounds belonging to the indole alkaloids. C1-Substituted optically active THβCs have been target extensive synthetic efforts due presence scaffold in numerous natural products and targets. This review briefly summarizes methods obtain C1 stereocenter concentrates on evaluating pharmacological importance C1-substituted THβCs, including their PDE5-inhibitory, antimalarial, antiviral antitumor activities.

参考文章(94)
John Franklin Miller, Ronald George Sherrill, Elizabeth Madalena Turner, Kristjan Gudmundsson, Useful compounds for hpv infection ,(2005)
Yun-Ping Zhou, Jin Shang, Nancy A. Thornberry, John R. Thompson, Jing Li, Weizhen Wu, Diagnosis and treatment of type 2 diabetes and other disorders ,(2006)
Manfred Hesse, Alkaloids: nature's curse or blessing? Alkaloids: nature's curse or blessing?. pp. 413- ,(2002)
Sarvajit Chakravarty, Rajendra Parasmal Jain, Pyrido[3,4-b]indoles and methods of use ,(2010)
Wei Bi, Jianhui Cai, Sanguang Liu, Michèle Baudy-Floc’h, Lanrong Bi, Design, synthesis and cardioprotective effect of a new class of dual-acting agents: Phenolic tetrahydro-β-carboline RGD peptidomimetic conjugates Bioorganic & Medicinal Chemistry. ,vol. 15, pp. 6909- 6919 ,(2007) , 10.1016/J.BMC.2007.08.022
Joachim Stöckigt, Andrey P. Antonchick, Fangrui Wu, Herbert Waldmann, The Pictet–Spengler Reaction in Nature and in Organic Chemistry Angewandte Chemie. ,vol. 50, pp. 8538- 8564 ,(2011) , 10.1002/ANIE.201008071
Daniel L. Priebbenow, Luke C. Henderson, Frederick M. Pfeffer, Scott G. Stewart, Domino heck-aza-michael reactions: efficient access to 1-substituted tetrahydro-β-carbolines Journal of Organic Chemistry. ,vol. 75, pp. 1787- 1790 ,(2010) , 10.1021/JO902652H
Oliver Rath, Frank Kozielski, Kinesins and cancer Nature Reviews Cancer. ,vol. 12, pp. 527- 539 ,(2012) , 10.1038/NRC3310
Nermin S. Ahmed, Bernard D. Gary, Hethar N. Tinsley, Gary A. Piazza, Stefan Laufer, Ashraf H. Abadi, Design, Synthesis and Structure–Activity Relationship of Functionalized Tetrahydro‐β‐carboline Derivatives as Novel PDE5 Inhibitors Archiv Der Pharmazie. ,vol. 344, pp. 149- 157 ,(2011) , 10.1002/ARDP.201000236
Jin Li, Tao Wang, Peng Yu, A. Peterson, R. Weber, D. Soerens, D. Grubisha, D. Bennett, J. M. Cook, General Approach for the Synthesis of Ajmaline/Sarpagine Indole Alkaloids: Enantiospecific Total Synthesis of (+)-Ajmaline, Alkaloid G, and Norsuaveoline via the Asymmetric Pictet−Spengler Reaction Journal of the American Chemical Society. ,vol. 121, pp. 6998- 7010 ,(1999) , 10.1021/JA990184L