Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy

doi:10.1007/s13659-014-0049-8

Natural Products and Bioprospecting ›› 2015, Vol. 5 ›› Issue (1): 37-45.DOI: 10.1007/s13659-014-0049-8

• Original article • Previous Articles Next Articles

Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy

Pei Cao¹, Zhen-Jie Li¹, Wen-Wu Sun^1,2, Shashwat Malhotra^3,4, Yuan-Liang Ma¹, Bin Wu¹, Virinder S. Parmar³

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India;
4. Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany

Received:2014-11-03 Revised:2014-11-27 Online:2018-02-11 Published:2015-02-24
Supported by:
This research was supported by grants from the "Hundred Talents Project" of Chinese Academy of Science and "High-end Science and Technology Talents Program" of Yunnan Province(2011HA008).

Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy

Pei Cao¹, Zhen-Jie Li¹, Wen-Wu Sun^1,2, Shashwat Malhotra^3,4, Yuan-Liang Ma¹, Bin Wu¹, Virinder S. Parmar³

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India;
4. Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany

通讯作者: Bin Wu,e-mail:wubin@mail.kib.ac.cn;Virinder S.Parmar,e-mail:virparmar@gmail.com
基金资助:
This research was supported by grants from the "Hundred Talents Project" of Chinese Academy of Science and "High-end Science and Technology Talents Program" of Yunnan Province(2011HA008).

Abstract

Abstract: The concise building of the spiroketal core of acortatarin-type alkaloids as potential therapeutic agents in diabetic nephropathy was established in four steps, through a tandem N-alkylation/hemiacetalization between pyrrole units and the corresponding halo alcohols generated by convenient halomethylation of chiral lactones from natural aldoses.

Key words: Acortatarin alkaloids, Diabetic nephropathy, N-alkylation/hemiacetalization, Halomethylation, Chiral lactones

摘要： The concise building of the spiroketal core of acortatarin-type alkaloids as potential therapeutic agents in diabetic nephropathy was established in four steps, through a tandem N-alkylation/hemiacetalization between pyrrole units and the corresponding halo alcohols generated by convenient halomethylation of chiral lactones from natural aldoses.

关键词: Acortatarin alkaloids, Diabetic nephropathy, N-alkylation/hemiacetalization, Halomethylation, Chiral lactones

Pei Cao, Zhen-Jie Li, Wen-Wu Sun, Shashwat Malhotra, Yuan-Liang Ma, Bin Wu, Virinder S. Parmar. Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy[J]. Natural Products and Bioprospecting, 2015, 5(1): 37-45.

References

1. X.G. Tong, L.L. Zhou, Y.H. Wang, C. Xia, Y. Wang, M. Liang, F.F. Hou, Y.X. Cheng, Org. Lett. 12, 1844 (2010)
2. J.L. Guo, Z.M. Feng, Y.J. Yang, Z.W. Zhang, P.C. Zhang, Chem. Pharm. Bull. 58, 983 (2010)
3. T. Yang, C.H. Wang, G.X. Chou, T. Wu, X.M. Cheng, Z.T. Wang, Food Chem. 123, 705 (2010)
4. G. Sudhakar, V.D. Kadam, S. Bayya, G. Pranitha, B. Jagadeesh, Org. Lett. 13, 5452 (2011)
5. H.M. Geng, J.L.Y. Chen, D.P. Furkert, S. Jiang, M.A. Brimble, Synlett 23, 855 (2012)
6. N.V. Borrero, A. Aponick, J. Org. Chem. 77, 8410 (2012)
7. J.M. Wurst, A.L. Verano, D.S. Tan, Org. Lett. 14, 4442 (2012)
8. T. Teranishi, M. Kageyama, S. Kuwahara, Biosci. Biotechnol. Biochem. 77, 676 (2013)
9. B. Bessières, C. Morin, J. Org. Chem. 68, 4100 (2003)
10. T. Tite, L. Tomas, T. Docsa, P. Gergely, J. Kovensky, D. Gueyrard, A. Wadouachi, Tetrahedron Lett. 53, 959 (2012)
11. S. Oscarson, F.W. Sehgelmeble, J. Org. Chem. 67, 8457 (2002)
12. A.C. Araújo, A.P. Rauter, F. Nicotra, C. Airoldi, B. Costa, L. Cipolla, J. Med. Chem. 54, 1266 (2011)
13. U. Wichai, S.A. Woski, Org. Lett. 1, 1173 (1999)
14. E. Block, E.V. Dikarev, R.S. Glass, J. Jin, B. Li, X. Li, S.Z. Zhang, J. Am. Chem. Soc. 128, 14949 (2006)
15. Y. Cen, A.A. Sauve, J. Org. Chem. 74, 5779 (2009)
16. D. Hou, H.A. Taha, T.L. Lowary, J. Am. Chem. Soc. 131, 12937 (2009)
17. A.K. Ghosh, S. Leshchenko, M. Noetzel, J. Org. Chem. 69, 7822 (2004)
18. V.A. Knizhnikov, N.E. Borisova, N.Y. Yurashevich, L.A. Popova, A.Y. Chernyad'ev, A.Y. Chernyad'ev, M.D. Reshetova, Russ. J. Org. Chem. 43, 855 (2007)
19. J.T. Gupton, E.J. Banner, M.D. Sartin, M.B. Coppock, J.E. Hempel, A. Kharlamova, D.C. Fisher, B.C. Giglio, K.L. Smith, M.J. Keough, T.M. Smith, R.P.F. Kanters, R.N. Dominey, J.A. Sikorski, Tetrahedron 64, 5246 (2008)
20. H.S. Jensen, G. Limberg, C. Pedersen, Carbohydr. Res. 302, 109 (1997)
21. K. Yamada, H. Fujita, M. Kunishima, Org. Lett. 14, 5026 (2012)
22. P. Setzer, A. Beauseigneur, M.S.M. Pearson-Long, P. Bertus, Angew. Chem. Int. Ed. Engl. 49, 8691 (2010)
23. V.J. Bulbule, P.S. Koranne, V.H. Deshpande, H.B. Borate, Tetrahedron 63, 166 (2007)
24. C.D. Donner, A.N. Cuzzupe, C.L. Falzon, M. Gill, Tetrahedron 68, 2799 (2012)

[1]	Hai-Hui Guo, Lei Wu, Dan Mi, Xing-Yu Zhang, Fu-Mei He, Ting Lei, Fu-Sheng Wang. Polysaccharide fraction from Triplostegia glandulifera Wall and its renoprotective effect in streptozotocin-induced diabetic mice by attenuating oxidative stress [J]. Natural Products and Bioprospecting, 2024, 14(5): 47-47.
[2]	Bangrui Huang, Rui Han, Hong Tan, Wenzhuo Zhu, Yang Li, Fakun Jiang, Chun Xie, Zundan Ren, Rou Shi. Scutellarin ameliorates diabetic nephropathy via TGF-β1 signaling pathway [J]. Natural Products and Bioprospecting, 2024, 14(3): 25-25.

Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy

Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments