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Chemical Compound Review

Pyrimidinamine     pyrimidin-2-amine

Synonyms: PubChem4106, CHEMBL88580, SureCN27136, AGN-PC-0D4UNI, SureCN726882, ...
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Disease relevance of Pyrimidinamine


High impact information on Pyrimidinamine

  • The mechanistic implications of the active site arrangement are discussed, including the potential role of the aminopyrimidine ring of the ThP2 [4].
  • In the present investigation, we describe novel substituted aminopyrimidine derivatives that inhibit human GSK-3 potently (K(i) < 10 nmol/l) with at least 500-fold selectivity against 20 other protein kinases [5].
  • An aminopyrimidine, PNU 112455A, was identified in a screen for inhibitors of cdk2 [6].
  • The new synthetic strategy is based on an electrophilic cyclization reaction involving an iminium intermediate formed by the corresponding aminopyrimidine with a carbonyl compound to give the desired heterocycles in high yields [7].
  • In this paper, we describe the synthesis, structure-activity relationships, and pharmacological characterization of 2-aminopyrimidine carbamates, a new class of compounds with potent and selective inhibition of Lck [8].

Biological context of Pyrimidinamine


Anatomical context of Pyrimidinamine


Associations of Pyrimidinamine with other chemical compounds


Gene context of Pyrimidinamine

  • For the wild-type transketolase complex with the 4'-methylamino analogue, no electron density was found for the methyl group in the X-ray structure, whereas in the complex with the N1'-methylated coenzyme the entire aminopyrimidine ring was disordered [17].
  • Two novel hypolipidaemic agents, both members of the aminopyrimidine series, with a mode of action of inhibition of oxidosqualene cyclase (OSC), were administered orally to dogs and mice for 14 and 28 days [18].
  • A novel series of aminopyrimidine IKK2 inhibitors have been developed which show excellent in vitro inhibition of this enzyme and good selectivity over the IKK1 isoform [19].
  • Thereafter, protected amino acids were coupled iteratively by the DCC method, commencing at the amino group of the aminopyrimidine unit [20].
  • Moreover, it could be proved that the mechanism of substrate activation of PDC (yeast) is also connected directly with the C2-H activation by the aminopyrimidine part [21].


  1. AMN107, a novel aminopyrimidine inhibitor of Bcr-Abl, has in vitro activity against imatinib-resistant chronic myeloid leukemia. Golemovic, M., Verstovsek, S., Giles, F., Cortes, J., Manshouri, T., Manley, P.W., Mestan, J., Dugan, M., Alland, L., Griffin, J.D., Arlinghaus, R.B., Sun, T., Kantarjian, H., Beran, M. Clin. Cancer Res. (2005) [Pubmed]
  2. AMN107, a novel aminopyrimidine inhibitor of p190 Bcr-Abl activation and of in vitro proliferation of Philadelphia-positive acute lymphoblastic leukemia cells. Verstovsek, S., Golemovic, M., Kantarjian, H., Manshouri, T., Estrov, Z., Manley, P., Sun, T., Arlinghaus, R.B., Alland, L., Dugan, M., Cortes, J., Giles, F., Beran, M. Cancer (2005) [Pubmed]
  3. Synthesis and fungitoxicity of some pyrimidine derivatives. Ouf, S.A., Sherif, S.M. Folia Microbiol. (Praha) (1993) [Pubmed]
  4. Crystal structure and mechanistic implications of N2-(2-carboxyethyl)arginine synthase, the first enzyme in the clavulanic acid biosynthesis pathway. Caines, M.E., Elkins, J.M., Hewitson, K.S., Schofield, C.J. J. Biol. Chem. (2004) [Pubmed]
  5. Selective glycogen synthase kinase 3 inhibitors potentiate insulin activation of glucose transport and utilization in vitro and in vivo. Ring, D.B., Johnson, K.W., Henriksen, E.J., Nuss, J.M., Goff, D., Kinnick, T.R., Ma, S.T., Reeder, J.W., Samuels, I., Slabiak, T., Wagman, A.S., Hammond, M.E., Harrison, S.D. Diabetes (2003) [Pubmed]
  6. The cyclin-dependent kinases cdk2 and cdk5 act by a random, anticooperative kinetic mechanism. Clare, P.M., Poorman, R.A., Kelley, L.C., Watenpaugh, K.D., Bannow, C.A., Leach, K.L. J. Biol. Chem. (2001) [Pubmed]
  7. Design and synthesis of a tetracyclic pyrimidine-fused benzodiazepine library. Zheng, L., Xiang, J., Dang, Q., Guo, S., Bai, X. Journal of combinatorial chemistry. (2006) [Pubmed]
  8. Novel 2-aminopyrimidine carbamates as potent and orally active inhibitors of Lck: synthesis, SAR, and in vivo antiinflammatory activity. Martin, M.W., Newcomb, J., Nunes, J.J., McGowan, D.C., Armistead, D.M., Boucher, C., Buchanan, J.L., Buckner, W., Chai, L., Elbaum, D., Epstein, L.F., Faust, T., Flynn, S., Gallant, P., Gore, A., Gu, Y., Hsieh, F., Huang, X., Lee, J.H., Metz, D., Middleton, S., Mohn, D., Morgenstern, K., Morrison, M.J., Novak, P.M., Oliveira-dos-Santos, A., Powers, D., Rose, P., Schneider, S., Sell, S., Tudor, Y., Turci, S.M., Welcher, A.A., White, R.D., Zack, D., Zhao, H., Zhu, L., Zhu, X., Ghiron, C., Amouzegh, P., Ermann, M., Jenkins, J., Johnston, D., Napier, S., Power, E. J. Med. Chem. (2006) [Pubmed]
  9. Analogues of 8-azaguanosine. Elliot, R.D., Montgomery, J.A. J. Med. Chem. (1976) [Pubmed]
  10. Nicosulfuron: alcoholysis, chemical hydrolysis, and degradation on various minerals. Sabadie, J. J. Agric. Food Chem. (2002) [Pubmed]
  11. Effects of AMN107, a novel aminopyrimidine tyrosine kinase inhibitor, on human mast cells bearing wild-type or mutated codon 816 c-kit. Verstovsek, S., Akin, C., Manshouri, T., Quintás-Cardama, A., Huynh, L., Manley, P., Tefferi, A., Cortes, J., Giles, F.J., Kantarjian, H. Leuk. Res. (2006) [Pubmed]
  12. Synthesis of N-10-methyl-4-thiofolic acid and related compounds. Elliott, R.D., Temple, C., Frye, J.L., Nontgomery, J.A. J. Med. Chem. (1975) [Pubmed]
  13. Aminopyrimidines with high affinity for both serotonin and dopamine receptors. Wustrow, D., Belliotti, T., Glase, S., Kesten, S.R., Johnson, D., Colbry, N., Rubin, R., Blackburn, A., Akunne, H., Corbin, A., Davis, M.D., Georgic, L., Whetzel, S., Zoski, K., Heffner, T., Pugsley, T., Wise, L. J. Med. Chem. (1998) [Pubmed]
  14. Homo- and heteroassemblies of lactim/lactam recognition patterns on highly ordered pyrolytic graphite: An STM investigation. Mourran, A., Ziener, U., Möller, M., Suarez, M., Lehn, J.M. Langmuir : the ACS journal of surfaces and colloids. (2006) [Pubmed]
  15. Prodrugs of 2',3'-didehydro-3'-deoxythymidine (D4T): synthesis, antiviral activity, and rapid pharmacokinetic evaluation. Tortolani, D.R., Russell, J.W., Whiterock, V.J., Hitchcock, M.J., Ghazzouli, I., Martin, J.C., Mansuri, M.M., Starrett, J.E. Journal of pharmaceutical sciences. (1994) [Pubmed]
  16. In vitro metabolism of isaxonine phosphate: formation of two metabolites, 5-hydroxyisaxonine and 2-aminopyrimidine, and covalent binding to microsomal proteins. Martinat, C., Amar, C., Dansette, P.M., Leclaire, J., Lopez-Garcia, P., Cao, T.D., N'Guyen, H.N., Mansuy, D. Eur. J. Pharmacol. (1992) [Pubmed]
  17. Effect of coenzyme modification on the structural and catalytic properties of wild-type transketolase and of the variant E418A from Saccharomyces cerevisiae. Golbik, R., Meshalkina, L.E., Sandalova, T., Tittmann, K., Fiedler, E., Neef, H., König, S., Kluger, R., Kochetov, G.A., Schneider, G., Hübner, G. FEBS J. (2005) [Pubmed]
  18. Toxicologic lesions associated with two related inhibitors of oxidosqualene cyclase in the dog and mouse. Pyrah, I.T., Kalinowski, A., Jackson, D., Davies, W., Davis, S., Aldridge, A., Greaves, P. Toxicologic pathology. (2001) [Pubmed]
  19. A novel series of potent and selective IKK2 inhibitors. Bingham, A.H., Davenport, R.J., Gowers, L., Knight, R.L., Lowe, C., Owen, D.A., Parry, D.M., Pitt, W.R. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  20. Estrano[17,16-e]pyrimidine-peptide conjugates. Matsumoto, T., Watanabe, M., Mataka, S., Thiemann, T. Steroids (2003) [Pubmed]
  21. Sixty years of thiamin diphosphate biochemistry. Schellenberger, A. Biochim. Biophys. Acta (1998) [Pubmed]
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