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Preliminary Communication

Design and Synthesis of a New Series of Highly Potent Raf Kinase-Inhibiting Triarylpyrazole Derivatives Possessing Antiproliferative Activity Against Melanoma Cells

, , , &
Pages 2197-2211 | Received 04 Mar 2016, Accepted 13 Jun 2016, Published online: 15 Nov 2016

References

  • Garbe C , HauschildA, VolkenandtMet al. Evidence and interdisciplinary consense-based German guidelines: diagnosis and surveillance of melanoma. Melanoma Res.17, 393–399 (2007).
  • Atallah E , FlahertyL. Treatment of metastatic malignant melanoma. Curr. Treat. Options Oncol.6, 185–193 (2005).
  • Barth A , WanekLA, MortonDL. Prognostic factors in 1,521 melanoma patients with distant metastases. J. Am. Coll. Surg.181, 193–201 (1995).
  • Anderson CM , BuzaidAC, LeghaSS. Systemic treatments for advanced cutaneous melanoma. Oncol. (Williston Park)9, 1149–1158 (1995).
  • Gray-Schopfer V , WellbrockC, MaraisR. Melanoma biology and new targeted therapy. Nature445, 851–857 (2007).
  • Garbe C , EigentlerTK. Diagnosis and treatment of melanoma: state of the art in 2006. Melanoma Res.17, 117–127 (2007).
  • Koon HB , AtkinsMB. Update on therapy for melanoma: opportunities for patient selection and overcoming tumor resistance. Expert Rev. Anticancer Ther.7, 79–88 (2007).
  • Smith RA , DumasJ, AdnaneL, WilhelmSM. Recent advances in the research and development of RAF kinase inhibitors. Curr. Top. Med. Chem.6, 1071–1089 (2006).
  • Brose MS , VolpeP, FeldmanMet al. BRAF and RAS mutations in human lung cancer and melanoma. Cancer Res.62, 6997–7000 (2002).
  • Wilhelm SM , CarterC, TangLet al. BAY 43–9006 exhibits broad spectrum oral antitumor activity and targets the RAF/MEK/ERK pathway and receptor tyrosine kinases involved in tumor progression and angiogenesis. Cancer Res.64, 7099–7109 (2004).
  • Mullard A . 2011 FDA drug approvals. Nat. Rev. Drug Discov.11, 91–94 (2012).
  • Luke JJ , HodiFS. Vemurafenib and BRAF inhibition: a new class of treatment for metastatic melanoma. Clin. Cancer Res.18, 9–14 (2012).
  • Long GV , StroyakovskiyD, GogasHet al. Combined BRAF and MEK inhibition versus BRAF inhibition alone in melanoma. N. Engl. J. Med.371, 1877–88 (2014).
  • El-Gamal MI , SimTB, HongJH, ChoJ-H, YooKH, OhC-H. Synthesis of 1H-pyrazole-1-carboxamide derivatives and their antiproliferative activity against melanoma cell line. Arch. Pharm. Chem. Life Sci.344, 197–204 (2011).
  • El-Gamal MI , OhC-H. Design and synthesis of 3-(3-chloro-4-substituted phenyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide derivatives and their antiproliferative activity against melanoma cell line. Bull. Korean Chem. Soc.32, 821–828 (2011).
  • El-Gamal MI , ChoiHS, ChoH-G, HongJH, YooKH, OhC-H. Design, synthesis and antiproliferative activity of 3,4-diarylpyrazole-1-carboxamide derivatives against melanoma cell line. Arch. Pharm. Chem. Life Sci.344, 745–754 (2011).
  • Choi W-K , El-GamalMI, ChoiHS, BaekD, OhC-H. New diarylureas and diarylamides containing 1,3,4-triarylpyrazole scaffold: synthesis, antiproliferative evaluation against melanoma cell lines, ERK kinase inhibition and molecular docking studies. Eur. J. Med. Chem.46, 5754–5762 (2011).
  • El-Gamal MI , ParkYS, ChiDY, YooKH, OhC-H. New triarylpyrazoles as broad-spectrum anticancer agents: design, synthesis and biological evaluation. Eur. J. Med. Chem.65, 315–322 (2013).
  • El-Gamal MI , ChoiHS, YooKH, BaekD, OhC-H. Antiproliferative diarylpyrazole derivatives as dual inhibitors of the ERK pathway and COX-2. Chem. Biol. Drug Des.82, 336–347 (2013).
  • Dean D , TakleA, WilsonD. Preparation of pyridylfurans and pyridylpyrroles as Raf kinase inhibitors. WO 03/022832 A1 (2003).
  • Reaction Biology Corp . www.reactionbiology.com
  • Corbeil CR , EnglebienneP, MoitessierN. Docking ligands into flexible and solvated macromolecules. 1. Development and validation of FITTED 1.0. J. Chem. Inf. Model.42, 435–449 (2007).
  • Corbeil CR , EnglebienneP, YannopoulosCGet al. Docking ligands into flexible and solvated macromolecules. 2. Development and application of FITTED 1.5 to the virtual screening of potential HCV polymerase inhibitors. J. Chem. Inf. Model.48, 902–909 (2008).
  • FITTED. The FITTED docking software. http://fitted.ca
  • RCSB Protein Data Bank . www.rcsb.org/pdb/home/home.do
  • Wan PT , GarnettMJ, RoeSMet al. Mechanism of activation of the RAF-ERK signaling pathway by oncogenic mutations of B-RAF. Cell116, 855–867 (2004).
  • Bollag G , HirthP, TsaiJet al. Clinical efficacy of a RAF inhibitor needs broad target blockade in BRAF-mutant melanoma. Nature467, 596–599 (2010).
  • Hatzivassiliou G , SongK, YenIet al. RAF inhibitors prime wild-type RAF to activate the MAPK pathway and enhance growth. Nature464, 431–435 (2010).
  • Perkin Elmer . www.cambridgesoft.com/
  • Biovia . http://accelrys.com/
  • Laskowski RA , SwindellsMB. LigPlot+: multiple ligand-protein interaction diagrams for drug discovery. J. Chem. Inf. Model.51, 2778–2786 (2011).
  • Weinstock J , GaitanopoulosD, OhHJet al. Synthesis and dopaminergic activity of some halogenated mono- and dihydroxylated 2- aminotetralins. J. Med. Chem.29, 1615–1627 (1986).
  • Claudi F , GiorgioniG, Di StefanoA, AbbracchioMP, PaolettiAM, BalduiniW. Synthesis and pharmacological characterization of 2-​(4-​chloro-​3-​hydroxyphenyl)​ethylamine and N,​N-​dialkyl derivatives as dopamine receptor ligands. J. Med. Chem.35, 4408–4414 (1992).
  • Sumitomo H , ImabayashiF, IwataT, KawakamiY. The BRAF–MAPK signaling pathway is essential for cancer-immune evasion in human melanoma cells. J. Exp. Med.203, 1651–1656 (2006).
  • Yang H , HigginsB, KolinskyK, PackmanK, GoZ, IyerR. RG7204 (PLX4032), a selective BRAFV600E inhibitor, displays potent antitumor activity in preclinical melanoma models. Cancer Res.70, 5518–5527 (2010).
  • Zheng B , JeongJH, AsaraJMet al. Oncogenic B-RAF negatively regulates the tumor suppressor LKB1 to promote melanoma cell proliferation. Mol. Cell33, 237–247 (2009).
  • Zhang J , YangPL, GrayNS. Targeting cancer with small molecule kinase inhibitors. Nat. Rev. Cancer9, 28–39 (2009).
  • Cell Bank Australia. Cell Line Information Sheet for MM127 . http://www.phe-culturecollections.org.uk/media/51798/MM127_13440210G_Episode_3_v02.pdf
  • RCSB. Protein Data Bank . http://www.rcsb.org/pdb/home/home.do

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