Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Straightforward Synthesis of K-7174, a GATA-Specific Inhibitor

  • Majik, Mahesh S. (Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University) ;
  • Yu, Jin-Ha (Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University) ;
  • Jeong, Lak-Shin (Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University)
  • Received : 2012.04.30
  • Accepted : 2012.05.29
  • Published : 2012.09.20
Download PDF
⟨ Previous Next ⟩

Abstract

K-7174, a GATA-specific inhibitor, is a putative anti-inflammatory agent that attenuates effects of inflammatory cytokines in certain cell types. An expeditious four-step synthesis of K-7174 is described in this paper. The route employs Wittig olefination and bis-alkylation of homopiperazine as the key reactions. The iodine-catalyzed isomerization of the Z-isomer results in complete conversion to the E-isomer is the highlight of our synthetic endeavors.

Keywords

References

  1. Maciag, A. E.; Nandurdikar, R. S.; Hong, S. Y.; Chakrapani, H.; Diwan, B.; Morris, N. L.; Shami, P. J.; Shiao, Y.-H.; Anderson, L. M.; Keefer, L. K.; Saavedra, J. E. J. Med. Chem. 2011, 54, 7751. https://doi.org/10.1021/jm2004128
  2. Bogatecheva, E.; Hanrahan, C.; Nikonenko, B.; Samala, R.; Chen, P.; Gearhart, J.; Barbosa, F.; Elinck, L.; Nacy, C. A.; Protopopova, M. J. Med. Chem. 2006, 49, 3045. https://doi.org/10.1021/jm050948+
  3. Coudert, P.; Rubat, C.; Bastide, M.; Malhuret, R.; Chopineau, J. J. Pharm. Belg. 1995, 50, 445.
  4. Brookes, P.; Terry, J.; Walker, J. J. Chem. Soc. 1957, 3165 https://doi.org/10.1039/jr9570003165
  5. Taillefumier, C.; Thielges, S.; Chapleur, Y. Tetrahedron 2004, 60, 2213. https://doi.org/10.1016/j.tet.2004.01.030
  6. Janin, Y.; Aubertin, A. M.; Chiaroni, A.; Riche, C.; Monneret, C.; Bisagani, E.; Grierson, D. S. Tetrahedron 1996, 52, 15157. https://doi.org/10.1016/S0040-4020(96)00952-0
  7. Lakatosh, S. A.; Luzikov, Y. N.; Preobrazhenskaya, M. N. Org. Biomol. Chem. 2003, 1, 826. https://doi.org/10.1039/b211163b
  8. Noriyuki, I. Jpn. Kokai Tokkyo Koho 2011, JP 2011001296 A 20110106.
  9. Spiegelman, B. M.; Flier, J. S. Cell 2001, 104, 531. https://doi.org/10.1016/S0092-8674(01)00240-9
  10. Charriere, G.; Cousin, B.; Arnaud, E.; Andre, M.; Bacou, F.; Penicaud, L.; Casteilla, L. J. Biol. Chem. 2003, 278, 9850 https://doi.org/10.1074/jbc.M210811200
  11. Hotamisligil, G. S.; Shargil, N. S.; Spiegelman, B. M. Science 1993, 259, 87. https://doi.org/10.1126/science.7678183
  12. Menghini, R.; Marchetti, V.; Cardellini, M.; Hribal, M. L.; Mauriello, A.; Lauro, D.; Sbraccia, P.; Lauro, R.; Federici, M. Circulation 2005, 111, 1946. https://doi.org/10.1161/01.CIR.0000161814.02942.B2
  13. Umetani, M.; Nakao, H.; Doi, T.; Iwasaki, A.; Ohtaka, M.; Nagoya, T.; Mataki, C.; Hamakubo, T.; Kodama, T. Biochem. Biophys. Res. Commun. 2000, 272, 370. https://doi.org/10.1006/bbrc.2000.2784
  14. Takano, Y.; Hiramatsu, N.; Okamura, M.; Hayakawa, K.; Shimada, T.; Kasai, A.; Yokouchi, M.; Shitamura, A.; Yao, J.; Paton, A. W.; Paton, J. C.; Kitamura, M. Biochem. Biophys. Res. Commun. 2007, 360, 470. https://doi.org/10.1016/j.bbrc.2007.06.082
  15. Imagawa, S.; Nakano, Y.; Obara, N.; Suzuki, N.; Doi, T.; Kodama, T.; Nagasawa, T.; Yamamoto, M. FASEB J. 2003, 17, 1742.
  16. Nakao, H.; Umetani, M.; Suda, M.; Nagoya, T. Cell Adhesion Inhibitor, EP 0774257
  17. Nakao, H.; Umetani, M.; Suda, M.; Nagoya, T. Cell Adhesion Inhibitor, JP 1997143075
  18. Nakao, H.; Umetani, M.; Suda, M.; Nagoya, T. Cell Adhesion Inhibitor, US 5723465.
  19. Wang, R.; Lu, S.-C.; Zhang, Y.-M.; Shi, Z.-J.; Zhang, W. Org. Biomol. Chem. 2011, 9, 5802. https://doi.org/10.1039/c1ob05082f
  20. Ding, M.-W.; Xiao, W.-J.; Lu, S.-M.; Huang, W.-F.; Shi, D.-Q. Heteroatom Chem. 1997, 8, 191. https://doi.org/10.1002/(SICI)1098-1071(1997)8:2<191::AID-HC12>3.0.CO;2-M
  21. Gosney, I.; Rowley, A. G. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: New York, 1997; pp 17-153.
  22. Vedajs, E.; Meier, G. P.; Snoble, K. A. J. Am. Chem. Soc. 1981, 103, 2823. https://doi.org/10.1021/ja00400a055
  23. Olah, G. A.; Krishnamurthy, V. V. J. Am. Chem. Soc. 1982, 104, 3987. https://doi.org/10.1021/ja00378a035
  24. Schlosser, M. Angew. Chem. Int. Ed. Engl. 1968, 7, 650.
  25. Schlosser, M.; Christmann, K. F.; Piskala, A.; Coffinet, D. Synthesis 1971, 29.
  26. Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 4245. https://doi.org/10.1021/ja00992a065
  27. Corey, E. J.; Yamamoto, H. J. Am. Chem. Soc. 1970, 92, 226, 6636. https://doi.org/10.1021/ja00704a052
  28. Noyes, R. M.; Dickinson, R. G.; Schomaker, V. J. Am. Chem. Soc. 1945, 67, 1319. https://doi.org/10.1021/ja01224a034
  29. Benson, S. W.; Egger, K. W.; Golden, D. M. J. Am. Chem. Soc. 1965, 87, 468. https://doi.org/10.1021/ja01081a013
  30. Yamashita, S. Bull. Chem. Soc. Jpn., 1961, 34, 972. https://doi.org/10.1246/bcsj.34.972
  31. Muizebelt, W. J.; Nivard, R. J. F. J. Chem. Soc., Chem. Commun. 1965, 8, 148.
  32. Muizebelt, W. J.; Nivard, R. J. F. J. Chem. Soc. B 1968, 8, 913.
  33. Gaukroger, K.; Hadfield, J. A.; Hepworth, L. A.; Lawrence, N. J.; McGown, A. T. J. Org. Chem. 2001, 66, 8135. https://doi.org/10.1021/jo015959z

Cited by

  1. Do reciprocal interactions between cell stress proteins and cytokines create a new intra-/extra-cellular signalling nexus? vol.18, pp.6, 2013, https://doi.org/10.1007/s12192-013-0444-9