Design and synthesis of phthalazine-based compounds as potent anticancer agents with potential antiangiogenic activity via VEGFR-2 inhibition

References

• Zhang YS, Liu Y, Chen D, et al. Synthesis and antitumor activities of novel 1,4-disubstituted phthalazine derivatives. Eur. J. Med. Chem 2010;45:3504–10.
   PubMed Web of Science ®Google Scholar
• Imramovský A, Jorda R, Pauk K, et al. Substituted 2-hydroxy-N-(arylalkyl)benzamides induce apoptosis in cancer cell lines. Eur J Med Chem 2013;68:253–9.
   PubMed Web of Science ®Google Scholar
• Renehan AG, Booth C, Potten CS. What is apoptosis, and why is it important? BMJ 2001;322:1536–8.
   PubMed Web of Science ®Google Scholar
• Zhang J, Yang PL, Gray NS. Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer 2009;9:28–39.
   PubMed Web of Science ®Google Scholar
• Cortes E, Ravandi F, O'Brien S, Kantarjian H. Targeted therapies in hematology and their impact on patient care: chronic and acute myeloid leukemia. Semin Hematol 2013;50:271–83.
   PubMed Web of Science ®Google Scholar
• Scott EN, Meinhardt G, Jacques C, et al. Vatalanib: the clinical development of a tyrosine kinase inhibitor of angiogenesis in solid tumours. Expert Opin Investig Drugs 2007;16:367–79.
   PubMed Web of Science ®Google Scholar
• Hasinoff BB, Pate D. The lack of target specificity of small molecule anticancer kinase inhibitors is correlated with their ability to damage myocytes in vitro. Toxicol Appl Pharm 2010;249:132–9.
   PubMed Web of Science ®Google Scholar
• Ricci MS, Kim SH, Ogi K, et al. Reduction of TRAIL-induced Mcl-1 and cIAP2 by c-Myc or sorafenib sensitizes resistant human cancer cells to TRAIL-induced death. Cancer Cell 2007;12:66–80.
   PubMed Web of Science ®Google Scholar
• Liu L, Cao Y, Chen C, et al. Sorafenib blocks the RAF/MEK/ERK pathway, inhibits tumor angiogenesis, and induces tumor cell apoptosis in hepatocellular carcinoma model PLC/PRF/5. Cancer Res 2006;66:11851–8.
   PubMed Web of Science ®Google Scholar
• Zhang W, Konopleva M, Ruvolo VR, et al. Sorafenib induces apoptosis of AML cells via Bim-mediated activation of the intrinsic apoptotic pathway. Leukemia 2008;22:808–18.
   PubMed Web of Science ®Google Scholar
• Chuma M, Terashita K, Sakamoto N. New molecularly targeted therapies against advanced hepatocellular carcinoma: From molecular pathogenesis to clinical trials and future directions. Hepatol Res 2015;45:E1–11.
   PubMed Web of Science ®Google Scholar
• Blanc J, Geney R, Menet C. Type II kinase inhibitors: an opportunity in cancer for rational design. Anticancer Agents Med Chem 2013;13:731–47.
   PubMed Web of Science ®Google Scholar
• Sodani K, Patel A, Anreddy N, et al. Telatinib reverses chemotherapeutic multidrug resistance mediated by ABCG2 efflux transporter in vitro and in vivo. Biochem Pharmacol 2014;89:52–61.
   PubMed Web of Science ®Google Scholar
• Garuti L, Roberti M, Bottegoni G. Small molecule aurora kinases inhibitors. Curr Med Chem 2009;16:1949–63.
   PubMed Web of Science ®Google Scholar
• Shallal HM, Russu WA. Discovery, synthesis, and investigation of the antitumor activity of novel piperazinylpyrimidine derivatives. Eur J Med Chem 2011;46:2043–57.
   PubMed Web of Science ®Google Scholar
• Rice KD, Kim MH, Bussenius J, et al. Pyrazolopyrimidines as dual Akt/p70S6K inhibitors. Bioorg Med Chem Lett 2012;22:2693–7.
   PubMed Web of Science ®Google Scholar
• Pollard JR, Mortimore M. Discovery and development of aurora kinase inhibitors as anticancer agents. J Med Chem 2009;52:2629–51.
   PubMed Web of Science ®Google Scholar
• Musumeci F, Radi M, Brullo C, Schenone S. Vascular endothelial growth factor (VEGF) receptors: drugs and new inhibitors. J Med Chem 2012;55:10797–822.
   PubMed Web of Science ®Google Scholar
• Abouzid KM, Khalil N, Ahmed E. Synthesis and evaluation of anti-proliferative activity of 1,4-disubstituted phthalazines. Med Chem Res 2012;21:3288–93.
   Web of Science ®Google Scholar
• Sammond DM, Veal JM, Nolte RT, et al. Discovery of a novel and potent series of dianilinopyrimidineurea and urea isostere inhibitors of VEGFR2 tyrosine kinase. Bioorg Med Chem Lett 2005;15:3519–23.
   PubMed Web of Science ®Google Scholar
• Stout DM, Matier WL, Barcelon-Yang C, et al. Synthesis and antiarrhythmic and parasympatholytic properties of substituted phenols. 3. Modifications to the linkage region (region 3). J Med Chem 1985;28:295–8.
   PubMed Web of Science ®Google Scholar
• Nakatsu MN, Sainson RCA, Aoto JN, et al. Angiogenic sprouting and capillary lumen formation modeled by human umbilical vein endothelial cells (HUVEC) in fibrin gels: the role of fibroblasts and Angiopoietin-1. Microvas Res 2003;66:102–12.
   PubMed Web of Science ®Google Scholar
• Park H-J, Zhang Y, Georgescu SP, et al. Human umbilical vein endothelial cells and human dermal microvascular endothelial cells offer new insights into the relationship between lipid metabolism and angiogenesis. Stem Cell Rev 2006;2:93–101.
   PubMed Web of Science ®Google Scholar
• Alley MC, Monks A, Hursey ML, et al. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res 1988;48:589–601.
   PubMed Web of Science ®Google Scholar
• Grever MR, Chabner BA. The National Cancer Institute: cancer drug discovery and development program. Semin Oncol 1992;19:622–38.
   PubMed Web of Science ®Google Scholar
• Jiang BH, Jiang G, Zheng JZ, et al. Phosphatidylinositol 3-kinase signaling controls levels of hypoxia-inducible factor 1. Cell Growth 2001;12:363–9.
   PubMedGoogle Scholar
• C, Behl C, Ziegler Cell aging: molecular mechanisms and implications for disease. 1st ed. Berlin Heidelberg: Springer-Verlag; 2014.
   Google Scholar
• Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61.
   PubMed Web of Science ®Google Scholar
• Wilcken R, Zimmermann MO, Lange A, et al. Principles and applications of halogen bonding in medicinal chemistry and chemical biology. J Med Chem 2013;56:1363–88.
   PubMed Web of Science ®Google Scholar
• Wilcken R, Zimmermann MO, Lange A, et al. Addressing methionine in molecular design through directed sulfur-halogen bonds. J Chem Theory Comput 2011;7:2307–15.
   PubMed Web of Science ®Google Scholar
• Zimmermann MO, Lange A, Boeckler FM. Evaluating the potential of halogen bonding in molecular design: automated scaffold decoration using the new scoring function XBScore. J Chem Inf Model 2015;55:687–99.
   PubMed Web of Science ®Google Scholar
• Smolyar NN, Yutilov YM. Cyclotransformation in the series of fused 5-nitropyridin-2(1H)-ones. Russ J Org Chem 2008;44:274–81.
   Web of Science ®Google Scholar
• Gabriel S, Neumann A. Umlagerung von Phtalidderivatenin AbkÖmmlinge des α γ - Diketohydrindens. Chemische Berichte 1893;26:708–9.
   Google Scholar
• Zhang QR, Xue DQ, He P, et al. Synthesis and antimicrobial activities of novel 1,2,4-triazolo [3,4-a] phthalazine derivatives. Bioorg Med Chem Letters 2014;24:1236–8.
   PubMed Web of Science ®Google Scholar