Neocryptolepine (Cryprotackieine), A Unique Bioactive Natural Product: Isolation, Synthesis, and Profile of Its Biological Activity

作者: Andrea B. J. Bracca , Daniel A. Heredia , Enrique L. Larghi , Teodoro S. Kaufman

DOI: 10.1002/EJOC.201402910

关键词: Biological activityTotal synthesisNatural productChemistryIsolation (microbiology)Organic chemistryCryptolepis sanguinolentaNeocryptolepine

摘要: The widely varying different approaches to the total synthesis of indoloquinoline alkaloid neocryptolepine are discussed. Aspects relating isolation natural product from Cryptolepis sanguinolenta, as well its performance in various biological tests and spectroscopic studies involving product, also reviewed.

参考文章(225)
E. Gellért, Raymond-Hamet, E. Schlittler, Die Konstitution des Alkaloids Cryptolepin Helvetica Chimica Acta. ,vol. 34, pp. 642- 651 ,(1951) , 10.1002/HLCA.19510340228
Shigeru Murata, Yasuhiro Tsubone, Reina Kawai, Daisuke Eguchi, Hideo Tomioka, Mechanistic studies of intramolecular CH insertion reaction of arylnitrenes: isotope effect, configurational purity and radical clock studies Journal of Physical Organic Chemistry. ,vol. 18, pp. 9- 20 ,(2005) , 10.1002/POC.837
Ning Wang, Kathryn Jean Wicht, Li Wang, Wen-Jie Lu, Ryuhei Misumi, Ming-qi Wang, Ahmed Abdel Aleem El Gokha, Marcel Kaiser, Ibrahim El Tantawy El Sayed, Timothy John Egan, Tsutomu Inokuchi, Synthesis and in vitro testing of antimalarial activity of non-natural-type neocryptolepines: structure–activity relationship study of 2,11- and 9,11-disubstituted 6-methylindolo[2,3-b]quinolines. Chemical & Pharmaceutical Bulletin. ,vol. 61, pp. 1282- 1290 ,(2013) , 10.1248/CPB.C13-00639
P. Vuorela, M. Leinonen, P. Saikku, P. Tammela, J.- Rauha, T. Wennberg, H. Vuorela, Natural Products in the Process of Finding New Drug Candidates Current Medicinal Chemistry. ,vol. 11, pp. 1375- 1389 ,(2004) , 10.2174/0929867043365116
K. Cimanga, T. De Bruyne, L. Pieters, J. Totte, L. Tona, K. Kambu, D. Vanden Berghe, A.J. Vlietinck, Antibacterial and antifungal activities of neocryptolepine, biscryptolepine and cryptoquindoline, alkaloids isolated from Cryptolepis sanguinolenta Phytomedicine. ,vol. 5, pp. 209- 214 ,(1998) , 10.1016/S0944-7113(98)80030-5
Colin W. Wright, Plant Derived Antimalarial Agents: New Leads and Challenges Phytochemistry Reviews. ,vol. 4, pp. 55- 61 ,(2005) , 10.1007/S11101-005-3261-7
Michael Schmittel, Jens-Peter Steffen, Miguel Á. Wencesla Ángel, Bernd Engels, Christian Lennartz, Michael Hanrath, Two Novel Thermal Biradical Cyclizations of Enyne-Ketenimines: Theory, Experiment, and Synthetic Potential Angewandte Chemie International Edition. ,vol. 37, pp. 1562- 1564 ,(1998) , 10.1002/(SICI)1521-3773(19980619)37:11<1562::AID-ANIE1562>3.0.CO;2-H
M. W. Partridge, J. M. Sprake, H. J. Vipond, Cyclic amidines. Part XX. Polyaza- and oxapolyaza-benzonaphthanthracenes Journal of The Chemical Society C: Organic. pp. 1245- 1249 ,(1966) , 10.1039/J39660001245
Mei‐Lin Go, None, Novel antiplasmodial agents. Medicinal Research Reviews. ,vol. 23, pp. 456- 487 ,(2003) , 10.1002/MED.10040
Lionel Guittat, Patrizia Alberti, Frédéric Rosu, Sabine Van Miert, Emilie Thetiot, Luc Pieters, Valérie Gabelica, Edwin De Pauw, Alexandre Ottaviani, Jean-François Riou, Jean-Louis Mergny, None, Interactions of cryptolepine and neocryptolepine with unusual DNA structures Biochimie. ,vol. 85, pp. 535- 547 ,(2003) , 10.1016/S0300-9084(03)00035-X