1,312
Views
21
CrossRef citations to date
0
Altmetric
Short Communication

Synthesis of new thieno[2,3-b]pyridine derivatives as pim-1 inhibitors

&
Pages 1718-1725 | Received 27 Jul 2015, Accepted 14 Feb 2016, Published online: 22 Mar 2016

References

  • Cusypers HT, Selten G, Quint W, et al Murine leukemia virus-induced T-cell lymphomagenesis: integration of proviruses in a distinct chromosomal region. Cell 1984;37:141–50
  • Drygin D, Haddach M, Pierre F, Ryckman DM. Potential use of selective and nonselective pim kinase inhibitors for cancer therapy. J Med Chem 2012;55:8199–208
  • Nawijn MC, Alendar A, Berns A. For better or for worse: the role of pim oncogenes in tumorigenesis. Nat Rev Cancer 2011;11:23–34
  • Merke AL, Meggers E, Ocker M. PIM1 kinase as a target for cancer therapy. Expert Opin Investig Drugs 2012;21:425–36
  • Morwick T. Pim kinase inhibitors: a survey of the patent literature. Expert Opin Ther Patents 2010;20:193–212
  • Guo S, Mao X, Chen J, et al Overexpression of pim-1 in bladder cancer. J Exp Clin Cancer Res 2010;29:161–7
  • Brault L, Gasser C, Bracher F, et al PIM serine/threonine kinases in the pathogenesis and therapy of hematologic malignancies and solid cancers. Haematologica 2010;95:1004–15
  • Arunesh GM, Shanthi E, Krishna MH, et al Small molecule inhibitors of PIM1 kinase: July 2009 to February 2013 patent update. Expert Opin Ther Patents 2014;24:5–17
  • Hirano T, Ishihara K, Hibi M. Roles of STAT3 in mediating the cell growth, differentiation and survival signals relayed through the IL-6 family of cytokine receptors. Oncogene 2000;19:2548–56
  • Bachmann M, Hennemann H, Xing PX, et al The oncogenic serine/threonine kinase pim-1 phosphorylates and inhibits the activity of Cdc25C-associated kinase 1 (C-TAK1): a novel role for pim-1 at the G2/M cell cycle checkpoint. J Biol Chem 2004;279:48319–28
  • Foulks JM, Carpenter KJ, Luo B, et al A small-molecule inhibitor of pim kinases as a potential treatment for urothelial carcinomas. Neoplasia 2014;16:403–12
  • Decker S, Finter J, Forde A, et al PIM kinases are essential for chronic lymphocytic leukemia cell survival (PIM2/3) and CXCR4-mediated microenvironmental interactions (PIM1). Mol Cancer Ther 2014;13:1231–45
  • Lu J, Zavorotinskaya T, Dai Y, et al Pim2 is required for maintaining multiple myeloma cell growth through modulating TSC2 phosphorylation. Blood 2013;122:1610–20
  • Ishchenko A, Zhang L, Le Brazidec JY, et al Structure-based design of low-nanomolar PIM kinase inhibitors. Bioorg Med Chem Lett 2015;25:474–80
  • Good AC, Liu J, Hirth B, et al Implications of promiscuous pim-1 kinase fragment inhibitor hydrophobic interactions for fragment-based drug design. J Med Chem 2012;55:2641–8
  • Cheney IW, Yan S, Appleby T, et al Identification and structure-activity relationships of substituted pyridones as inhibitors of pim-1 kinase. Bioorg Med Chem Lett 2007;17:1679–83
  • Anizon F, Shtil AA, Danilenko VN, Moreau P. Fighting tumor cell survival: advances in the design and evaluation of pim inhibitors. Curr Med Chem 2010;17:4114–33
  • Schenone S, Tintori C, Botta M. Using insights into pim-1 structure to design new anticancer drugs. Curr Pharm Des 2010;16:3964–78
  • Blanco-Aparicio C, Collazo AM, Oyarzabal J, et al Pim 1 kinase inhibitor ETP-45299 suppresses cellular proliferation and synergizes with PI3K inhibition. Cancer Lett 2011;300:145–53
  • Chen LS, Redkar S, Taverna P, et al Mechanisms of cytotoxicity to pim kinase inhibitor, SGI-1776, in acute myeloid leukemia. Blood 2011;118:693–702
  • Pierre F, Stefan E, Nédellec AS, et al 7-(4H-1,2,4-Triazol-3-yl)benzo[c][2,6]naphthyridines: a novel class of pim kinase inhibitors with potent cell antiproliferative activity. Bioorg Med Chem Lett 2011;21:6687–92
  • Tao ZF, Hasvold LA, Leverson JD, et al Discovery of 3H-benzo[4,5]thieno[3,2-d]pyrimidin-4-ones as potent, highly selective, and orally bioavailable inhibitors of the human protooncogene proviral insertion site in moloney murine leukemia virus (pim) kinases. J Med Chem 2009;52:6621–36
  • Tsuhako AL, Brown DS, Koltun ES, et al The design, synthesis, and biological evaluation of PIM kinase inhibitors. Bioorg Med Chem Lett 2012;22:3732–8
  • Xiang Y, Hirth B, Asmussen G, et al The discovery of novel benzofuran-2-carboxylic acids as potent pim-1 inhibitors. Bioorg Med Chem Lett 2011;21:3050–6
  • Bullock AN, Debreczeni J, Amos AL, et al Structure and substrate specificity of the pim-1 kinase. J Biol Chem 2005;280:41675–82
  • Qian KC, Wang L, Hickey ER, et al Structural basis of constitutive activity and a unique nucleotide binding mode of human pim-1 kinase. J Biol Chem 2005;280:6130–7
  • Madkour HMF, Afify AAE, Abdalha AA, et al Synthetic utility of enaminonitrile moiety in heterocyclic synthesis: synthesis of some new thienopyrimidines. Phosphorus Sulfur Silicon Relat Elem 2009;184:719–32
  • Rajak H, Kumar P, Parmar P, et al Appraisal of GABA and PABA as linker: design and synthesis of novel benzamide based histone deacetylase inhibitors. Eur J Med Chem 2012;53:390–7
  • Martin H. Quaternary ammonioalkanecarboxylic acid anilides as plant growth influencing agents. U.S. patent 1979;2,141,718
  • Zimam EH. Synthesis, characterization and study biological activity of some new sulphadiazine derivatives. Int J Chem Natur Sci 2014;2:109–15
  • Dalalian HP, Rutherford NJ, Kushner S. Acylpiperazines and methods of preparing the same. U.S. patent, 1957;2,807,617
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63
  • Scudiere DA, Shoemaker RH, Paul KD, et al Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res 1988;48:4827–33
  • http://www.molinspiration.com/cgi-bin/properties [last accessed 8 Mar 2016]

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.