DOI QR코드

DOI QR Code

Solid-phase Parallel Synthesis of a Novel N-[Alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted Amide and Amine Drug-like Libraries

  • Kim, Ji-Hye (Center for Innovative Drug Library Research, Department of Chemistry, Dongguk University) ;
  • Gong, Young-Dae (Center for Innovative Drug Library Research, Department of Chemistry, Dongguk University) ;
  • Lee, Gee-Hyung (Center for Innovative Drug Library Research, Department of Chemistry, Dongguk University) ;
  • Seo, Jin-Soo (Center for Drug Discovery Platform Technology, Korea Research Institute of Chemical Technology)
  • 투고 : 2011.11.01
  • 심사 : 2011.11.11
  • 발행 : 2012.01.20

초록

We report the solid-phase library construction of 222 number of a novel N-[alkyl sulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B derivatives. The polymer-bound N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 9 and amine 10 derivatives were obtained by first diversity generation with various acid chlorides and alkyl halides. Further reactions on the resins 9 and 10 with substituted sulfonyl chlorides produced the desired N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B analogues.

키워드

참고문헌

  1. Krchnak, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61. https://doi.org/10.1021/cr010123h
  2. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. https://doi.org/10.1021/cr9402081
  3. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. https://doi.org/10.1016/0040-4020(95)00467-M
  4. Yoo, S.-E.; Seo, J.-S.; Yi, K. Y.; Gong, Y.-D. Tetrahedron Lett. 1997, 38, 1203. https://doi.org/10.1016/S0040-4039(97)00017-8
  5. Yoo, S.-E.; Gong, Y.-D.; Seo, J.-S.; Sung, M. - M.; Lee, S.; Kim, Y. J. Comb. Chem. 1999, 1, 177. https://doi.org/10.1021/cc980029n
  6. Gong, Y.- D.; Yoo, S.-E. Bull. Kor. Chem. Soc. 2001, 21, 941.
  7. Gong. Y.- D.; Seo, J.-S.; Chon, Y.-S.; Hwang, J.-Y.; Park, J.-Y.; Yoo, S.-E. J. Comb. Chem. 2003, 5, 577. https://doi.org/10.1021/cc030014b
  8. Lee, I. Y.; Kim. S. Y.; Lee, J. Y.; Yu, C.-M.; Lee, D. H.; Gong, Y.-D. Tetrahedron Lett. 2004, 45, 9319. (f) Hwang, J. Y.; Choi, H.-S.; Lee, D.-H.; Yoo, S.-E.; Gong, Y.-D. J. Comb. Chem. 2005, 1, 136.
  9. Hwang, J. Y.; Choi, H.-S.; Seo, J.-S.; La, H. J.; Kim, D.-S.; Jeon, H. S.; Jeon, M.-K.; Lee, D.- H.; Gong, Y.-D. J. Org. Chem. 2005, 70, 10151. https://doi.org/10.1021/jo051740z
  10. Ashwood, V. A.; Buckingham, R. E.; Cassidy, F.; Evans, J. M.; Faruk, E. A.; Hamilton, T. C.; Nash, D. J.; Stemp, G.; Willcocks, K. J. Med. Chem. 1986, 29, 2194. https://doi.org/10.1021/jm00161a011
  11. Bergmann, R.; Eierman, V.; Gericke, R. J. Med. Chem. 1990, 33, 2759. https://doi.org/10.1021/jm00172a013
  12. Hiessbock, R.; Wolf, C.; Richter, E.; Hitzler, M.; Chiba, P.; Kratzel, M.; Ecker, G. J. Med. Chem. 1999, 42, 1921. https://doi.org/10.1021/jm980517+
  13. Lee, T. T.-Y.; Kashiwada, Y.; Huang, I.; Snider, J.; Cosentino, M.; Lee, K.-H. Bioorg. Med. Chem. 1994, 2, 1051. https://doi.org/10.1016/S0968-0896(00)82054-4
  14. Cho, Y. S.; Song, J. S.; Huh, J. Y.; Kim, C. H.; Gong, Y.-D.; Cheon, H. G. Pharmacology, 2011, 87, 49. https://doi.org/10.1159/000322642
  15. Gong, Y.-D.; Cheom, H. G.; Lee, T. H.; Bae, M. S.; Kang, N. S. Bull. Kor. Chem. Soc. 2011, 32, 3752. https://doi.org/10.5012/bkcs.2011.32.10.3752
  16. Fernandez-Forner, D.; Huerta, J. M.; Ferrer, M.; Casals, G.; Ryder, H.; Giralt, E.; Albericio, F. Tetrahedron Lett. 2002, 43, 3543. https://doi.org/10.1016/S0040-4039(02)00564-6
  17. Alsina, J.; Yokum, T. S.; Albericio, F.; Barany, G. Tetrahedron Lett. 2000, 41, 7277. https://doi.org/10.1016/S0040-4039(00)01255-7
  18. Jensen, K. J.; Alsina, J.; Songster, M. F.; Vagner, J.; Albericio, F.; Barany, G. J. Am. Chem. Soc. 1998, 120, 5441. https://doi.org/10.1021/ja974116f
  19. Fivush, A. M.; Willson, T. M. Tetrahedron Lett. 1997, 38, 7151. https://doi.org/10.1016/S0040-4039(97)01771-1
  20. Ouyang, X.; Tamayo, N.; Kiselyov, A. S. Tetrahedron 1999, 55, 2827. https://doi.org/10.1016/S0040-4020(99)00061-7
  21. AMEBA resin was prepared from Merrifield resin by known method; Katritzky, A. R.; Toader, D.; Watson, K.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 7849. https://doi.org/10.1016/S0040-4039(97)10132-0
  22. Boojamra, C. G.; Burow, K. M.; Thompson, L. A.; Ellman, J. A. J. Org. Chem. 1997, 62, 1240. https://doi.org/10.1021/jo9622845
  23. Gong, Y.-D.; Cheon, H. G.; Jeon, M. K.; Cho, Y. S.; Seo, J. S.; Yoo, S.-E. Korea Patent No. 10-0746939.
  24. Lipinski, C. A.; Lombardo, F.; Doming, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3. https://doi.org/10.1016/S0169-409X(96)00423-1
  25. Oprea, T. I. Property Distribution of Drug-Related Chemical Databases. J. Comput. Aided Mol. Des. 2000, 14, 251. https://doi.org/10.1023/A:1008130001697
  26. Veber, D. F.; Johnson, S. R.; Cheng, H.-J.; Smith, B. R.; Ward, K. W.; Kopple, K. D. J. Med. Chem. 2002, 45, 2615. https://doi.org/10.1021/jm020017n
  27. Accord for Excel, Version 6.1, Synopsys Scientific Systems, Ltd., 5 North Hill Road, Headingley, Leeds, U.K.

피인용 문헌

  1. Solid-Phase Parallel Synthesis of Drug-Like Artificial 2H-Benzopyran Libraries vol.17, pp.5, 2012, https://doi.org/10.3390/molecules17055467
  2. Discovery of a Novel 2,6-Difunctionalized 2H-Benzopyran Inhibitors Toward Sphingosylphosphorylcholine Synthetic Pathway as New Anti-inflammatory Target vol.35, pp.8, 2012, https://doi.org/10.5012/bkcs.2014.35.8.2385