DOI QR코드

DOI QR Code

Synthesis of Formylchromone Derivatives; Inactivators of Protein Tyrosine Phosphatase 1B

  • Shrestha, Suja (Department of Chemistry and Institute of Molecular Cell Biology, Inha University) ;
  • Hwang, Su-Yeon (Department of Chemistry and Institute of Molecular Cell Biology, Inha University) ;
  • Lee, Keun-Hyeung (Department of Chemistry and Institute of Molecular Cell Biology, Inha University) ;
  • Cho, Hyeong-Jin (Department of Chemistry and Institute of Molecular Cell Biology, Inha University)
  • Published : 2005.07.20

Abstract

Keywords

References

  1. Zhang, Z.-Y. Annu. Rev. Pharmacol. Toxicol. 2002, 42, 209 https://doi.org/10.1146/annurev.pharmtox.42.083001.144616
  2. Cohen, P. Trends Biochem. Sci. 2000, 25, 596 https://doi.org/10.1016/S0968-0004(00)01712-6
  3. Neel, B. G.; Tonks, N. K. Curr. Opin. Cell Biol. 1997, 9, 193 https://doi.org/10.1016/S0955-0674(97)80063-4
  4. Van Huijsduijnen, R. H.; Bombrun, A.; Swinnen, D. Drug Discov. Today 2002, 7, 1013 https://doi.org/10.1016/S1359-6446(02)02438-8
  5. Zhang, Z.-Y. Curr. Opin. Chem. Biol. 2001, 5, 416 https://doi.org/10.1016/S1367-5931(00)00223-4
  6. Li, L.; Dixon, J. E. Semin. Immunol. 2000, 12, 75 https://doi.org/10.1006/smim.2000.0209
  7. Elchebly, M.; Payette, P.; Michaliszyn, E.; Cromlish, W.; Collins, S.; Loy, A. L.; Normandin, D.; Cheng, A.; Himms-Hagen, J.; Chan, C. C.; Ramachandran, C.; Gresser, M. J.; Tremblay, M. L.; Kennedy, B. P. Science 1999, 283, 1544 https://doi.org/10.1126/science.283.5407.1544
  8. Zinker, B. A.; Rondinone, C. M.; Trevillyan, J. M.; Gum, R. J.; Clampit, J. E.; Waring, J. F.; Xie, N.; Wilcox, D.; Jacobson, P.; Frost, L.; Kroeger, P. E.; Reilly, R. M.; Koterski, S.; Opgenorth, T. J.; Ulrich, R. G.; Crosby, S.; Butler, M.; Murray, S. F.; McKay, R. A.; Bhanot, S.; Monia, B. P.; Jirousek, M. R. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 11357
  9. Shim, Y. S.; Kim, K. C.; Lee, K. A.; Shrestha, S.; Lee, K.-H.; Kim, C. K.; Cho, H. Bioorg. Med. Chem. 2005, 13, 1325 https://doi.org/10.1016/j.bmc.2004.11.006
  10. Shim, Y. A.; Kim, K. C.; Chi, D. Y.; Lee, K.-H.; Cho, H. Bioorg. Med. Chem. Lett. 2003, 13, 2561 https://doi.org/10.1016/S0960-894X(03)00479-7
  11. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron 1974, 30, 3553 https://doi.org/10.1016/S0040-4020(01)97034-6
  12. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron Lett. 1973, 22, 1995
  13. Reynolds, G. A.; Van Allan, J. A. J. Heterocyclic Chem. 1969, 6, 375 https://doi.org/10.1002/jhet.5570060316
  14. Sabitha, G. Aldrichim. Acta 1996, 29, 15
  15. Schiessler, R. W.; Rytina, A. W.; Whitmore, F. C. J. Am. Chem. Soc. 1948, 70, 529 https://doi.org/10.1021/ja01182a029
  16. Gribble, G. W.; Leese, R. M. Synthesis 1977, 172
  17. Nutaitis, C. F.; Patragnoni, R.; Goodkin, G.; Neighbour, B.; Obaza-Nutaitis, J. Org. Prep. Proced. Int. 1991, 23, 403 https://doi.org/10.1080/00304949109458225
  18. Wrobel, J.; Sredy, J.; Moxham, C.; Dietrich, A.; Li, Z.; Sawicki, D. R.; Seestaller, L.; Wu, L.; Katz, A.; Sullivan, D.; Tio, C.; Zhang, Z.-Y. J. Med. Chem. 1999, 42, 3199 https://doi.org/10.1021/jm990260v
  19. Suzuki, A. J. Organomet. Chem. 1999, 576, 147 https://doi.org/10.1016/S0022-328X(98)01055-9
  20. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457 https://doi.org/10.1021/cr00039a007
  21. Nakano, K.; Nakayachi, T.; Yasumoto, E.; Morshed, S. R. M. D.; Hashimoto, K.; Kikuchi, H.; Nishikawa, H.; Sugiyama, K.; Amano, O.; Kawase, M.; Sakagami, H. Anticancer Res. 2004, 24, 711
  22. Foltnova, P.; Lacova, M.; Loos, D. Il Farmaco 2000, 55, 21 https://doi.org/10.1016/S0014-827X(99)00114-7
  23. Hafez, M. E.-S.; Pavlina, F.; Margita, L.; Jarmila, C.; Henrieta, S. Il Farmaco 1998, 53, 224 https://doi.org/10.1016/S0014-827X(98)00015-9

Cited by

  1. Synthesis, characterization, NLO study, and antimicrobial activities of metal complexes derived from 3-(3-(2-hydroxyphenyl)-3-oxoprop-1-enyl)-4H-chromen-4-one and sulfanilamide vol.64, pp.10, 2011, https://doi.org/10.1080/00958972.2011.579116
  2. 3-Formylchromones as diverse building blocks in heterocycles synthesis vol.4, pp.3, 2013, https://doi.org/10.5155/eurjchem.4.3.311-328.815
  3. Efficient Catalytic Activity of Transition Metal Ions in Vilsmeier-Haack Reactions with Acetophenones pp.05388066, 2013, https://doi.org/10.1002/kin.20807
  4. Chromone: A Valid Scaffold in Medicinal Chemistry vol.114, pp.9, 2014, https://doi.org/10.1021/cr400265z
  5. -1-benzopyran-3-carboxaldehyde vol.51, pp.S1, 2014, https://doi.org/10.1002/jhet.2001
  6. ]thiophenes via Cu-Catalyzed α-C–H Functionalization of 2-Halochalcones Using Xanthate vol.19, pp.7, 2017, https://doi.org/10.1021/acs.orglett.7b00462
  7. Design, synthesis, characterization and antibacterial properties of copper(II) complexes with chromone-derived compounds pp.10990739, 2010, https://doi.org/10.1002/aoc.1587
  8. Vilsmeier-Haack reaction pp.19435193, 2010, https://doi.org/10.1002/jhet.338
  9. Synthesis of Formylchromone Derivatives; Inactivators of Protein Tyrosine Phosphatase 1B. vol.36, pp.49, 2005, https://doi.org/10.1002/chin.200549126
  10. A Facile Synthesis of Cyclopenta[d][1,2]oxazines through [6+4] Cycloaddition Reaction vol.27, pp.9, 2005, https://doi.org/10.5012/bkcs.2006.27.9.1481
  11. First Concise Total Synthesis of Biologically Interesting Natural Licoagrochalcone B and Its Unnatural Derivatives vol.28, pp.12, 2007, https://doi.org/10.5012/bkcs.2007.28.12.2523
  12. Mono- and disalicylic acid derivatives: PTP1B inhibitors as potential anti-obesity drugs vol.15, pp.20, 2007, https://doi.org/10.1016/j.bmc.2007.07.010
  13. The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C–H/Aromatic C–H Cross-Coupling vol.138, pp.27, 2005, https://doi.org/10.1021/jacs.6b05273
  14. Detection of HSO 3 : A Rapid Colorimetric and Fluorimetric Selective Sensor for Detecting Biological SO 2 in Food and Living Cells vol.2, pp.12, 2005, https://doi.org/10.1021/acsomega.7b01218