Lead identification of conformationally restricted benzoxepin type combretastatin analogs: synthesis, antiproliferative activity, and tubulin effects

References

• Jordan MA, Wilson L.Microtubules as a target for anticancer drugs. Nat Rev Cancer2004, 4: 253–65.
   PubMed Web of Science ®Google Scholar
• Jordan MA. Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Curr Med Chem Anticancer Agents 2002;2:1–17.
   PubMedGoogle Scholar
• Attard G, Greystoke A, Kaye S, De Bono J. Update on tubulin-binding agents. Pathol Biol (Paris) 2006;54:72–84.
   PubMedGoogle Scholar
• Tron GC, Pagliai F, Del Grosso E, Genazzani AA, Sorba G. Synthesis and cytotoxic evaluation of combretafurazans. J Med Chem 2005;48:3260–8.
   PubMed Web of Science ®Google Scholar
• ter Haar E, Rosenkranz HS, Hamel E, Day BW. Computational and molecular modeling evaluation of the structural basis for tubulin polymerization inhibition by colchicine site agents. Bioorg Med Chem 1996;4:1659–71.
   PubMed Web of Science ®Google Scholar
• Rai SS, Wolff J. Localization of the vinblastine-binding site on beta-tubulin. J Biol Chem 1996;271:14707–11.
   PubMed Web of Science ®Google Scholar
• Pettit GR, Singh SB, Boyd MR, Hamel E, Pettit RK, Schmidt JM, et al. Antineoplastic agents. 291.Isolation and synthesis of combretastatins A-4, A-5, and A-6(1a). J Med Chem 1995;38:1666–72.
   PubMed Web of Science ®Google Scholar
• Andreu JM, Barasoain I. The interaction of baccatin III with the taxol binding site of microtubules determined by a homogeneous assay with fluorescent taxoid. Biochemistry 2001;40:11975–84.
   PubMed Web of Science ®Google Scholar
• Diaz JF, Barasoain I, Andreu JM. Fast kinetics of Taxol binding to microtubules. Effects of solution variables and microtubule-associated proteins. J Biol Chem 2003;278:8407–19.
   PubMed Web of Science ®Google Scholar
• Pettit GR, Rhodes MR, Herald DL, Hamel E, Schmidt JM, Pettit RK. Antineoplastic agents. 445. Synthesis and evaluation of structural modifications of (Z)- and (E)-combretastatin A-41. J Med Chem 2005;48:4087–99.
   PubMed Web of Science ®Google Scholar
• Pettit GR, Singh SB, Hamel E, Lin CM, Alberts DS, Garcia-Kendall D. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4. Experientia 1989;45:209–11.
   PubMedGoogle Scholar
• Hori K. Antineoplastic strategy: irreversible tumor blood flow stasis induced by the combretastatin A-4 derivative AVE8062 (AC7700). Chemotherapy 2005;51:357–60.
   PubMed Web of Science ®Google Scholar
• Nam NH. Combretastatin A-4 analogues as antimitotic antitumor agents. Curr Med Chem 2003;10:1697–722.
   PubMed Web of Science ®Google Scholar
• Bailly C, Bal C, Barbier P, Combes S, Finet JP, Hildebrand MP, et al. Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins. J Med Chem 2003;46:5437–44.
   PubMed Web of Science ®Google Scholar
• Ganina OG, Daras E, Bourgarel-Rey V, Peyrot V, Andresyuk AN, Finet JP, et al. Synthesis and biological evaluation of polymethoxylated 4-heteroarylcoumarins as tubulin assembly inhibitor. Bioorg Med Chem 2008;16:8806–12.
   PubMed Web of Science ®Google Scholar
• Kim Y, Nam NH, You YJ, Ahn BZ. Synthesis and cytotoxicity of 3,4-diaryl-2(5H)-furanones. Bioorg Med Chem Lett 2002;12:719–22.
   PubMed Web of Science ®Google Scholar
• Wang L, Woods KW, Li Q, Barr KJ, McCroskey RW, Hannick SM, et al. Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. J Med Chem 2002;45:1697–711.
   PubMed Web of Science ®Google Scholar
• Pirali T, Busacca S, Beltrami L, Imovilli D, Pagliai F, Miglio G, et al. Synthesis and cytotoxic evaluation of combretafurans, potential scaffolds for dual-action antitumoral agents. J Med Chem 2006;49:5372–6.
   PubMed Web of Science ®Google Scholar
• Medarde M, Ramos A, Caballero E, de Clairac RPL, Lopez JL, Gravalos DG, et al. Synthesis and antineoplastic activity of combretastatin analogues: heterocombretastatins. Eur J Med Chem 1998;33:71–7.
   Web of Science ®Google Scholar
• De Martino G, La Regina G, Coluccia A, Edler MC, Barbera MC, Brancale A, et al. Arylthioindoles, potent inhibitors of tubulin polymerization. J Med Chem 2004;47:6120–3.
   PubMed Web of Science ®Google Scholar
• Lloyd DG, Hughes RB, Zisterer DM, Williams DC, Fattorusso C, Catalanotti B, et al. Benzoxepin-derived estrogen receptor modulators: a novel molecular scaffold for the estrogen receptor. J Med Chem 2004;47:5612–15.
   PubMed Web of Science ®Google Scholar
• Meegan MJ, Barrett I, Zimmermann J, Knox AJ, Zisterer DM, Lloyd DG. Benzothiepin-derived molecular scaffolds for estrogen receptor modulators: synthesis and antagonistic effects in breast cancer cells. J Enzyme Inhib Med Chem 2007;22:655–66.
   PubMed Web of Science ®Google Scholar
• Cushman M, Nagarathnam D, Gopal D, Chakraborti AK, Lin CM, Hamel E. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J Med Chem 1991;34:2579–88.
   PubMed Web of Science ®Google Scholar
• Freedman JS, Kenneth T. The preparation of 3,4-dihydro-1-benzoxepin-5(2H)-ones. J Heterocycl Chem 1989;26:1547–54.
   Web of Science ®Google Scholar
• Tandon VK, Khanna JM, Arand N, Srimal RC, Prasad CR. Agents acting on the central nervous system. XX.5-Subsitituted and 4,5-disubstituted 2,3,4,5-tetrahydro-1-benzoxepines. Indian J Chem 1975;13:1–8.
   Google Scholar
• ACD/Chemsketch v10. Atlanta, GA: Advanced Chemistry Labs (http://www.acdlabs.com/download/chemsk.html).
   Google Scholar
• Molecular Operating Environment (MOE). Montreal: Chemical Computing Group (http://www.chemcomp.com).
   Google Scholar
• Zhang SX, Feng J, Kuo SC, Brossi A, Hamel E, Tropsha A, et al.Antitumor agents. 199. Three-dimensional quantitative structure-activity relationship study of the colchicine binding site ligands using comparative molecular field analysis. J Med Chem 2000;43:167–76.
   PubMed Web of Science ®Google Scholar
• Boland GM, Donnelly DMX, Finet JP, Rea MD. Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins. J Chem Soc Perkin Trans 1 1996;(21):2591–7.
   Google Scholar
• Flynn BL, Flynn GP, Hamel E, Jung MK. The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4. Bioorg Med Chem Lett 2001;11:2341–3.
   PubMed Web of Science ®Google Scholar
• Gaukroger K, Hadfield JA, Lawrence NJ, Nolan S, McGown AT. Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? Org Biomol Chem 2003;1:3033–7.
   PubMed Web of Science ®Google Scholar
• Lawrence NJ, Hepworth LA, Rennison D, McGown AT, Hadfield JA. Synthesis and anticancer activity of fluorinated analogues of combretastatin A-4. J Fluorine Chem 2003;123:101–8.
   Web of Science ®Google Scholar
• Maya AB, del Rey B, Lamamie de Clairac RP, Caballero E, Barasoain I, Andreu JM, et al. Design, synthesis and cytotoxic activities of naphthyl analogues of combretastatin A-4. Bioorg Med Chem Lett 2000;10:2549–51.
   PubMed Web of Science ®Google Scholar
• Ravelli RB, Gigant B, Curmi PA, Jourdain I, Lachkar S, Sobel A, et al. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature 2004;428:198–202.
   PubMed Web of Science ®Google Scholar
• Jordan A, Hadfield JA, Lawrence NJ, McGown AT. Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle. Med Res Rev 1998;18:259–96.
   PubMed Web of Science ®Google Scholar
• Springer C, Adalsteinsson H, Young MM, Kegelmeyer PW, Roe DC. PostDOCK: a structural, empirical approach to scoring protein ligand complexes. J Med Chem 2005;48:6821–31.
   PubMed Web of Science ®Google Scholar