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DOI: 10.1055/s-0034-1380415
Bis(indolyl)methane Alkaloids: Isolation, Bioactivity, and Syntheses
Publikationsverlauf
Received: 30. Januar 2015
Accepted after revision: 16. April 2015
Publikationsdatum:
19. Mai 2015 (online)
Abstract
Bis(indolyl)methane (BIM) alkaloids are an important group of bioactive natural products predominantly found in marine organisms. Thus, compounds like arsindoline A and B, vibrindole A, arundine, and trisindoline are found in marine bacteria, while the related compound, streptindole is obtained from Streptococcus faecium IB 37, found in human feces. In recent years, these molecules, which display a wide range of biological properties (antibacterial, antiviral, anti-oxidant, neurotoxic activity etc.), have attracted the attention of several synthetic and natural product chemists. This review lists selected bis(indolyl)methane analogues reported from different natural sources to date, together with their biological properties and synthesis.
1 Introduction
2 Occurrence, Isolation, Structure Elucidation, and Biological Activity
3 Synthetic Approaches towards Bis(indolyl)methanes
4 Conclusions
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References
- 1 Kochanowska-Karamyan AJ, Hamann MT. Chem. Rev. 2010; 110: 4489
- 2 Bifulco G, Bruno I, Minale L, Riccio R, Calignano A. J. Nat. Prod. 1994; 57: 1294
- 3 Fattorusso E, Taglialatela-Scafati O. Modern Alkaloids . Wiley-VCH; Weinheim: 2008
- 4 Haiwei G, Zhengfeng X. Chin. J. Org. Chem. 2012; 32: 1195
- 5 Kaishap PP, Dohutia C. Int. J. Pharm. Sci. Rev. Res. 2013; 4: 1312 ; http://ijpsr.com/
- 6 Osawa T, Namiki M. Tetrahedron Lett. 1983; 24: 4719
- 7 Bell R, Carmeli S, Sar N. J. Nat. Prod. 1994; 57: 1587
- 8 Kamal A, Ali Qureshi A. Tetrahedron 1963; 19: 513
- 9 Zee SH, Chen CS. J. Chin. Chem. Soc. 1974; 21: 229
- 10 Singh H, Singh K. Tetrahedron 1988; 44: 5897
- 11 Kobayashi M, Aoki S, Gato K, Matsunami K, Kurosu M, Kitagawa I. Chem. Pharm. Bull. 1994; 42: 2449
- 12 Veluri R, Oka I, Wagner-Döbler I, Laatsch H. J. Nat. Prod. 2003; 66: 1520
- 13 Fatima I, Ahmad I, Anis I, Malik A, Afza NI. Molecules 2007; 12: 155 ; http://www.mdpi.com/journal/molecules
- 14 Khuzhaev BU, Aripova SF, Shakirov RS. Chem. Nat. Compd. 1994; 30: 635
- 15 Cai S.-X, Li D.-H, Zhu T.-J, Wang F.-P, Xiao X, Gu Q.-Q. Helv. Chim. Acta 2010; 93: 791
- 16 Hogan IT, Sainsbury M. Synthesis 1984; 872
- 17 Julia M, Tilly G. Bull. Soc. Chim. Fr. 1965; 2175
- 18 Meyers AI, Nabeya A, Adickes HW, Politzer IR, Malone GR, Kovelesky AC, Nolen RC, Portnoy RC. J. Org. Chem. 1973; 38: 36
- 19 Denis JN, Mauger H, Vallée Y. Tetrahedron Lett. 1997; 38: 8515
- 20 Mauger HC, Denis JN, Pouchot MT. A, Vallée Y. Tetrahedron 2000; 56: 791
- 21 Bartoli G, Bosco M, Foglia G, Giuliani A, Marcantoni E, Sambri L. Synthesis 2004; 895
- 22 Sato S, Sato T. Carbohydr. Res. 2005; 340: 2251
- 23 Chakrabarty M, Ghosh N, Basak R, Harigaya Y. Synth. Commun. 2004; 34: 421
- 24 Azizi N, Torkian L, Saidi MR. J. Mol. Catal. A: Chem. 2007; 275: 109
- 25 Chakrabarty M, Ghosh N, Basak R, Harigaya Y. Tetrahedron Lett. 2002; 43: 4075
- 26 Karthik M, Magesh CJ, Perumal PT, Palanichamy M, Arabindoo B, Murugesan V. Appl. Catal., A 2005; 286: 137
- 27 Banerjee B, Mandal SK, Roy SC. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2007; 46: 669
- 28 Kumar S, Grover IS, Sandhu JS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2009; 48: 585
- 29 Guo X, Pan S, Liu J, Li Z. J. Org. Chem. 2009; 74: 8848
- 30 Surasani R, Kalita D, Chandrasekhar KB. Green Chem. Lett. Rev. 2013; 6: 113
- 31 Jella RR, Nagarajan R. Tetrahedron 2013; 69: 10249
- 32 Abe T, Nakamura S, Yanada R, Choshi T, Hibino S, Ishikura M. Org. Lett. 2013; 15: 3622
- 33 Beltra J, Gimeno MC, Herrera RP. Beilstein J. Org. Chem. 2014; 10: 2206
- 34 Xiang J, Wang J, Wang M, Meng X, Wu A. Org. Biomol. Chem. 2015; 13: 4240