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제113회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthetic approach towards new bioactive piperidine alkaloids

2014년 2월 13일 15시 54분 39초
ORGN.P-766 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
4월 16일 (수요일) 16:00~19:00
저자 및
KONGARADAMODAR, 문인수1, 전종갑1,*
한림대학교 응용화학연구소, Korea
1한림대학교 화학과, Korea
Nitrogen containing compounds are very widely distributed in nature and are essential to life. They play a vital role in the metabolism of all living cells. At present, greater than 75% drugs and drug candidates incorporate amine functionality.1 Among the numerous naturally occurring nitrogen containing compounds, piperidine skeleton is an important structural feature found in various secondary metabolites and biologically active compounds.2 In particular, simple 2-alkyl-piperidines3 [e.g.; coniine 1 and pipecolic acid 2] have become important targets for the synthesis over the past few decades due to their scarcity in natural sources, wide array of structural diversity and notable physiological effects. Herein, we wish to present the synthetic approach towards new bioactive piperidines of this class using N-tert-butanesulfinyl imines which can be prepared from readily available chiral N-tert-butanesulfinamide and aldehyde (or ketone), exhibit unique reactivity, hydrolytic stability and stereoselectivity in various reactions have been proven to be extremely versatile chiral reagents.4 References: 1. MDL. MDL Drug Data Report. MDL Information System Inc. San Leandro CA; G. Liu, O. A. Cogan, J. A. Ellman. J. Am. Chem. Soc. 1997, 119, 9913. 2. (a) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1986; Vol. 26, p 89; (b) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Properties; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 3, p 1. 3. For reviews on piperidine alkaloids, see: (a) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581. (b) Hammann, P. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim; 1995; pp 323. (c) Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1996; Vol. 10, pp 155. (d) O’Hagan, D. Nat. Prod. Rep. 2000, 17, 435. (e) Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Comm. 1998, 633. 4. Robak, M. T.; Herbage, M. A., Ellman, J. A. Chem. Rev. 2010, 110, 3600.