Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Synthesis of New Aminopyrimidinylmethanone Derivatives

새로운 Aminopyrimidinylmethanone 유도체의 합성

  • Yoo, Kyung-Ho (Life Sciences Research Division, Korea Institute of Science and Technology) ;
  • Ahn, Hye-Mi (Life Sciences Research Division, Korea Institute of Science and Technology)
  • 유경호 (한국과학기술연구원 생체과학연구본부) ;
  • 안혜미 (한국과학기술연구원 생체과학연구본부)
  • Published : 2009.03.30
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Abstract

In this work, the synthetic approaches for a series of aminopyrimiclinylmethanone derivatives 1a-i, which versatile biological activities such as antibacterial and anticancer activities are expected from a structural point of view, were described. Nicotinic acid was converted to (2-methylsulfonylpyrimidin-4-yl) (pyridin-3-yl)methanone, a key intermediate, which was reacted with nucleophiles to yield the desired aminopyrimidinylmethanone derivatives 1a-i bearing various substituents.

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References

  1. R. Paul, W. A. Hallett, ]. W. Hanifin, M.F. Reich, B. D. Johnson, R. H. Lenhard, ].P. Dusza, S. S. Kerwar, Y-i Lin, W. C.Pickett, C. M. Seifert, L. W. Torley, M.E. Tarrant, and S. Wrenn, Preparation ofSubstituted N-Phenyl-4-aryl-2-pyrimidinaminesas Mediator Release Inhibitors, JMed Chem, 36, 2716 (1993) https://doi.org/10.1021/jm00071a002
  2. P. J. Barnes, New Drugs for Asthma,Nat. Rev. Drug Discov., 3, 831 (2004) https://doi.org/10.1038/nrd1524
  3. N. Sirisoma, S. Kasibhatla, B. Nguyen, A.Pervin, Y. Wang, G. Claassen, B. Tseng,]. Crewe, and S. X. Cai, Discovery ofSubstituted 4-Anilino-2-(2-pyridyJ)-pyrimidines as a New Series of ApoptosisInducers Using a Cell- and CaspasebasedHigh Throughput Screening Assay.Part 1: Structure-activity Relationships ofthe 4-Anilino Group. Bioorg. Med Chem,14, 7761 (2006) https://doi.org/10.1016/j.bmc.2006.08.002
  4. S. K. Kelley and A. Ashkenazi, TargetingDeath Receptors in Cancer withApo2L1TRAIL, Curro Opin Pharmacol., 4,333 (2004) https://doi.org/10.1016/j.coph.2004.02.006
  5. D. R. Batt, G. Bold, S. Kim, T. M.Ramsey, and M. L. Sabio. Preparation ofN-Aryl(heteroarylalkyI)isoquinolineaminesas a Inhibitors of Mutant and Wild-typeMAP Kinases for the Treatment ofCancer. WO 2004080464
  6. S. Kumar, ]. Boehm, and J. c. Lee, p38MAP Kinases: Key Signalling Moleculesas Therapeutic Targets for InflammatoryDiseases, Nat. Rev. Drug Discov., 2, 717(2003) https://doi.org/10.1038/nrd1177
  7. J. Dixon, J. Dumas, C. Brennan, H,Hatoum-Mokdad, W. Lee, R. Sibley, andB. Bear, Preparation of 2-Phenylarnino-4-(5-pyrazolylamino)-pyrimidines as KinaseInhibitors, In Particular, SRC KinaseInhibitors. WO 2003026664
  8. X. Cao., Q.-D. You, Z.i-Y. Li, X.-].Wang, X.-Y. Lu, x.o-R. Liu, D. Xu, andB. Liu, Recent Progress of Src FamilyKinase Inhibitors as Anticancer Agents,Mini Rev. Med Chem 8, 1053 (2008)
  9. J.-M. Jimenez, G. Bemis, F. Maltais, T.Wang, R. Knegtel, C. Davis, D. Fraysse,D. Boyall, L. Settimo, S. Young, and M.Mortimore, 2-Aminopyridine DerivativesUseful as Kinase Inhibitors, WO2008094992
  10. M. E. M. Noble, ]. A. Endicott, and L. N.Johnson, The Akt/PKB Family of ProteinKinases: A Review of Small MoleculeInhibitors and Progress towards TargetValidation, Science, 303, 1800 (2004) https://doi.org/10.1126/science.1095920
  11. P. Kirkpatrick, Kinases: New Route toKinase Inhibition, Nat. Rev. Drug Discov.,5, 104 (2006)
  12. M. Remuinan, J. J. Gonzalez, C. Del Pozo,A. Francesch, C. Cuevas, S. Munt, and I.Manzanares, Variolin Derivatives andTheir Use as Antitumor Agents, WO2003006457
  13. B. A. Johns, K. S. Gudmundsson, E. M.Turner, S. H. Allen, V. A. Samano, ]. A.Ray, G. A. Freeman, F. L. Boyd Jr., c. ].Sexton, W. Selleseth, K. L. Creech, andK. R. Moniri, PyrazolopyridineAntiherpetics: SAR of C2' and C7Amine Substituents, Bioorg. Med Chem,13, 2397 (2005) https://doi.org/10.1016/j.bmc.2005.01.044
  14. M. Hosseini-Sarvari and H. Sharghi, ZnOas a New Catalyst for N-Formylation ofAmines under Solvent-Free Conditions, J.Org. Chern., 71, 6652 (2006) https://doi.org/10.1021/jo060847z
  15. A. Gopalsamy, H. Yang, ]. W. Ellingboe,]. C. McKew, S. Tam, D.Joseph-McCarthy, W. Zhang, M. Shen,and ]. D. Clark 1,2,4-0xadiazolidin-3,5-diones and 1,3,5-Triazin-2,4,6-triones asCytosolic Phospholipase A2U Inhibitors,Bioorg. Med Chem Lett., 16, 2978(2006) https://doi.org/10.1016/j.bmcl.2006.02.067