Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Protein Tyrosine Phosphatase 1B Inhibitors: Heterocyclic Carboxylic Acids

  • Cho, Sung-Yun (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Ahn, Jin-Hee (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Ha, Jae-Du (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Kang, Seung-Kyu (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Baek, Ji-Yoen (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Han, Sang-Sub (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Shin, Eun-Young (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Kim, Sung-Soo (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Kim, Kwang-Rok (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Cheon, Hyae-Gyeong (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Choi, Joong-Kwon (Medicinal Science Division, Korea Research Institute of Chemical Technology)
  • Published : 2003.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Several series of compounds (benzoic acids, pyrazolecarboxylic acids, phenoxyacetic acids, and quinolinoxyacetic acids) were prepared and evaluated for their inhibitory activity against PTP-1B. Several compounds showed submicromolar inhibitory activity.

Keywords

References

  1. Kennedy, B. P.; Ramachandran, C. Biochem. Pharmacol. 2000,60, 877. https://doi.org/10.1016/S0006-2952(00)00305-1
  2. Moller, N.; Iversen, L.; Andersen, H.; McCormack, J.Curr. Opin. Drug Discov. Dev. 2000, 3, 527.
  3. 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
  4. Evans, J. L.; Jallal, B. Exp. Opin. Invest. Drugs 1999, 8, 139. https://doi.org/10.1517/13543784.8.2.139
  5. Johnson, T. O.; Ermolieff, J.; Jirousek, M. R. Nature Reviews/Drug Discovery 2002, 1, 696 https://doi.org/10.1038/nrd895
  6. Van Huijsduijnen, R. H.; Bombrun,A.; Swinnen, D. Drug Discovery Today 2002, 7, 1013. https://doi.org/10.1016/S1359-6446(02)02438-8
  7. Larsen, S. D.; Barf, T.; Liljebris, C.; May, P. D.; Ogg, D.; O'Sullivan,T. J.; Palazuk, B. J.; Schostarez, H. J.; Stevens, F. C.; Bleasdale, J.E. J. Med. Chem. 2002, 45, 598 and references cited therein. https://doi.org/10.1021/jm010393s
  8. Ahn, J. H.; Cho, S. Y.; Ha, J. D.; Chu, S. Y.; Jung, S. H.; Jung,Y. S.; Baek, J. Y.; Choi, I. K.; Shin, E. Y.; Kang, S. K.; Kim, S. S.;Cheon, H. G.; Yang, S. D.; Choi J.-K. Bioorg. Med. Chem. Lett.2002, 12, 1941. https://doi.org/10.1016/S0960-894X(02)00331-1
  9. Ahn, J. H.; Cho, S. Y.; Ha, J. D.; Kang, S. K.;Jung, S. H.; Kim, H.-M.; Baek, J. Y.; Han, S. S.; Shin, E. Y.; Kim,S. S.; Kim, K. R.; Cheon, H. G.; Yang, S. D.; Choi, J.-K. Bull.Korean Chem. Soc. 2003, in press.
  10. Satoh, T.; Itaya, T.; Miura, M.; Nomura, M. Chem. Lett. 1996, 823.
  11. Saunders, J. C.; Williamson, W. R. N. J. Med. Chem. 1979, 22, 1554. https://doi.org/10.1021/jm00198a026
  12. Yum, E. K.; Kang, S. K.; Choi, J.-K. Bull. Korean Chem. Soc.2001, 22, 644.
  13. Miyaura, M.; Suzuki, A. Chem. Rev. 1995, 95, 2457. https://doi.org/10.1021/cr00039a007

Cited by

  1. Discovery of Orally Active, Potent, and Selective Benzotriazole-Based PTP1B Inhibitors vol.6, pp.6, 2011, https://doi.org/10.1002/cmdc.201100077
  2. Synthesis, Structural Study and Spectroscopic Characterization of a Quinolin-8-Yloxy Derivative with Potential Biological Properties vol.02, pp.01, 2013, https://doi.org/10.4236/ojsta.2013.21002
  3. Regio- and stereoselective (3 + 2)-cycloaddition of nitrile oxides and nitrones to N-vinylindole vol.53, pp.2, 2017, https://doi.org/10.1134/S107042801702018X
  4. Study of Hybrid Heterocyclic's as Potential Nematicidal Agents pp.0022152X, 2017, https://doi.org/10.1002/jhet.2943
  5. Protein Tyrosine Phosphatase 1B Inhibitors: Heterocyclic Carboxylic Acids. vol.35, pp.7, 2004, https://doi.org/10.1002/chin.200407105
  6. Ruthenium-Catalyzed Synthesis of 3-Substituted Quinolines from 2-Aminobenzyl Alcohol and Aldehydes vol.26, pp.12, 2003, https://doi.org/10.5012/bkcs.2005.26.12.2038
  7. Unexpected Behavior of 5-Phenoxypyrazole Derivatives vol.26, pp.4, 2003, https://doi.org/10.5012/bkcs.2005.26.4.668
  8. Synthesis of Quinolines via Pd/C-Catalyzed Cyclization of 2-Aminobenzyl Alcohol with Ketones vol.26, pp.8, 2005, https://doi.org/10.5012/bkcs.2005.26.8.1286
  9. A Facile Synthesis of Cyclopenta[d][1,2]oxazines through [6+4] Cycloaddition Reaction vol.27, pp.9, 2003, https://doi.org/10.5012/bkcs.2006.27.9.1481
  10. Synthesis andin vitrostudy of a new class of methylene-bis-4,6-diarylbenzo[d]isoxazoles as potential antifungal agents vol.46, pp.3, 2003, https://doi.org/10.1002/jhet.100
  11. Inhibition of Protein Tyrosine Phosphatase 1β by Hispidin Derivatives Isolated from the Fruiting Body of Phellinus linteus vol.5, pp.12, 2003, https://doi.org/10.1177/1934578x1000501218
  12. Synthesis and structural and vibrational analysis of (5,7-dichloro-quinolin-8-yloxy) acetic acid vol.1018, pp.None, 2003, https://doi.org/10.1016/j.molstruc.2012.03.013