Convenient and efficient microwave-assisted synthesis of a methyl derivative of the fused indoloquinoline alkaloid cryptosanguinolentine

Molecules

Volumn 15, Issue 5, 2010, Pages 3171-3178

  Gengan, Robert M ^a   Pandian, Pitchai ^a,b   Kumarsamy, Chandraprakash ^b   Mohan, Palathurai S ^b  

^a DURBAN UNIVERSITY OF TECHNOLOGY   (South Africa)

^b BHARATHIAR UNIVERSITY   (India)

Author keywords

Cryptosanguinolentine; Microwave; Phase transfer catalysis

Indexed keywords

2-METHYLQUINOLINE; ALKALOID; CRYPTOSANGUINOLENTINE; INDOLE ALKALOID; INDOLE DERIVATIVE; QUINALDINE; QUINALDINE DERIVATIVE; QUINOLINOL DERIVATIVE;

ARTICLE; METHYLATION; MICROWAVE RADIATION; SYNTHESIS;

ALKALOIDS; HYDROXYQUINOLINES; INDOLE ALKALOIDS; INDOLEQUINONES; METHYLATION; MICROWAVES; QUINALDINES;

EID: 77952822942     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15053171     Document Type: Article

References (19)

1. Sharaf, M.H.M.; Schiff, P.L.; Tackie, A.N.; Phoebe, C.H.; Martin, G.E. Two new indoloquinoline alkaloids from Cryptolepis sanguinolenta: cryptosanguinolentine and cryptotackieine. J. Heterocycl. Chem. 1996, 33, 239-243.
2. Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinick, A. New alkaloids from Cryptolepis sanguinolenta. Tetrahedron Lett. 1996, 37, 1703-1706.
3. Karou, D.; Savadogo, A.; Canini, A.; Yameogo, S.; Montesano, C.; Simpore, J.; Colizzi, V.; Traore, A.S. Antibacterial activity of alkaloids from Sida acuta. Afr. J. Biotechnol. 2006, 5, 195-200.
4. Ansah. C.; Gooderham, N.J. The popular herbal antimalarial, extract of Cryptolepis sanguinolenta, is potently cytotoxic. Toxicol. Sci. 2002, 70, 45-251; and the references cited therein.
5. Bierer, D.E.; Fort, D.M.; Mendez, C.D.; Luo, J.; Imbach, P.A.; Dubenko, L.G.; Jolad, S.D.; Gerber, R.E.; Litvak, J.; Lu, Q.; Zhang, P.; Reed, M.J.; Waldeck, N.; Bruening, R.C.; Noamesi, B.K.; Hector, R.F.; Carlson, T.J.; King, S.R. Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities. J. Med. Chem. 1998, 41, 894-901.
6. Blinov, K.; Elyashberg, M.; Martirosian, E.R.; Molodtsov, S.G.; Williams, A.J.; Tackie, A.N.; Sharaf, M.M.H.; Schiff, P.L.; Crouch, R.C.; Martin, G.E.; Hadden, C.E.; Guido, J.E.; Mills, K.A. Quindolinocryptotackieine: the elucidation of a novel indoloquinoline alkaloid structure through the use of computer-assisted structure elucidation and 2D NMR. Magn. Reson. Chem. 2003, 41, 577-584; and the references sited therein.
7. Peczyriskc-Czoch,W.; Pognan, F.; Kaczmarck, L.; Boratyriski, J. Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b] quinolines: Novel cytotoxic, DNA topoisomerase II inhibitors. J. Med. Chem. 1994, 37, 3503-3510.
8. Sundaram, G.S.M.; Venkatesh, C.; Kumar, U.K.S.; Ila, H.; Junjappa, H. A concise formal synthesis of alkaloid cryptotackiene and substituted 6H-indolo[2,3-b]quinolines, J. Org. Chem. 2004, 69, 5760-5762.
9. Jaromin, A.; Kozubek, A. Liposomal formulation of DIMIQ, potential antitumor indolo[2,3- b]quinoline agent and its cytotoxicity on hepatoma morris 5123 cells. Drug Delivery 2008, 15, 49-56; and the references cited therein.
10. Kaczmarek, L.; Peczynska-Czoch, W.; Opolski, A.; Wietrzyk, J.; Marcinkowska, E.; Boratynski, J.; Osiadacz, J. Methoxy- and methyl-, methoxy- 5,6,11-trimethyl-6H-indolo[2,3-b]quinolinium derivatives as novel cytotoxic agents and DNA topoisomerase II inhibitors. Anticancer Res. 1998, 18, 3133-3138.
11. Molina, P.; Fresneda, P.M.; Delgado, S. Iminophosphorane-mediated synthesis of the alkaloid cryptotackieine. Synthesis 1999, 2, 326-329.
12. Molina, P.; Alajarin, M.; Vidal, A. New methodology for the preparation of pyrrole and indole derivatives via iminophosphoranes: synthesis of pyrrolo[1,2-a]quinoxalines, indolo[3,2- c]quinolines and indolo[1,2-c] quinazolines. Tetrahedron 1990, 46, 1063-1078.
13. Fresneda, M.; Molina, P.; Delgado, S. A divergent approach to cryptotackieine and cryptosanguinolentine alkaloids. Tetrahedron Lett. 1999, 40, 7275-7278.
14. Trecourt, F.; Mongin, F.; Mallet, M.; Queguiner, G. Substituted 8-methoxyquinolines: regioselective bromination, coupling reactions and cyclization to an 11 H-indolo[3,2-C]quinoline. Synth. Commun. 1995, 25, 4011-4024.
15. Timari, G.; Soos, T.; Hajos, G. A Convenient synthesis of two new indoloquinoline alkaloids. Synlett 1997, 1067-1068.
16. Kumar, R.N.; Suresh, T.; Mohan, P.S. A photochemical route to synthesize cryptosanguinolentine. Tetrahedron Lett. 2002, 43, 3327-3328.
17. Dhanabal, T.; Sangeetha, R.; Mohan, P.S. Fischer indole synthesis of the indoloquinoline alkaloid: cryptosanguinolentine. Tetrahedron Lett. 2005, 46, 4509-4510.
18. Dhanabal, T.; Sangeetha, R.; Mohan, P.S. Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives. Tetrahedron 2006, 62, 6258-6263.
19. Pitchai, P.; Mohan, P.S.; Gengan, R.M. Photo induced synthesis of methyl derivative of cryptosanguinolenine. Indian J. Chem. Sec.B. Org. Chem. Incl. Med. Chem. 2009, 48B, 692-696.