Design, synthesis and anticancer activities of halogenated Phenstatin analogs as microtubule destabilizing agent

Acharya BR, Bhattacharyya S, Choudhury D, Chakrabarti G (2011) The microtubule depolymerizing agent naphthazarin induces both apoptosis and autophagy in A549 lung cancer cells. Apoptosis 16:924–939 Álvarez C, Álvarez R, Corchete P, Pérez-Melero C, Peláez R, Medarde M (2010) Exploring the effect of 2,3,4-trimethoxy-phenyl moiety as a component of indolephenstatins. Eur J Med Chem 45:588–597 Beale TM, Myers RM, Shearman JW, Charnock-Jones DS, Brenton JD, Gergely FV, Ley SV (2010) Antivascular and anticancer activity of dihalogenated A-ring analogues of combretastatin A-4. Med Chem Commun 1:202–208 Gaspari R, Prota AE, Bargsten K, Cavalli A, Steinmetz MO (2017) Structural basis of cis-and trans-combretastatin binding to tubulin. Chem 2:102–113 Gaukroger K, Hadfield JA, Lawrence NJ, Nolan S, McGown AT (2003) Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? Org Biomol Chem 1:3033–3037 Kingston DG (2009) Tubulin-interactive natural products as anticancer agents. J Nat Prod 72:507–515 Li M, Tian YS (2016) Progress in synthesis and anti-tumor activities of combretastatin A4 derivatives. J Pharm Res 35:283–289 Lin CM, Ho HH, Pettit GR, Hamel E (1989) Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 28:6984–6991 Marrelli M, Conforti FA, Statti G, Cachet X, Michel S, Tillequin F, Menichini F (2011) Biological potential and structure-activity relationships of most recently developed vascular disrupting agents: an overview of new derivatives of natural combretastatin A-4. Curr Med Chem 18:3035–3081 Nguyen TL, McGrath C, Hermone AR, Burnett JC, Zaharevitz DW, Day BW, Wipf P, Hamel E, Gussio R (2005) A common pharmacophore for a diverse set of colchicine site inhibitors using a structure-based approach. J Med Chem 48:6107–6116 Pettit GR, Anderson CR, Herald DL, Jung MK, Lee DJ, Hamel E, Pettit RK (2003) Antineoplastic agents. 487. Synthesis and biological evaluation of the antineoplastic agent 3,4-methylenedioxy-5,4‘-dimethoxy-3’-amino-Z-stilbene and derived amino acid amides. J Med Chem 46:525–531 Pettit GR, Cragg GM, Herald DL, Schmidt JM, Lohavanijaya P (1982) Isolation and structure of combretastatin. Can J Chem 60:1374–1376 Pettit GR, Grealish MP, Herald DL, Boyd MR, Hamel E, Pettit RK (2000) Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug. J Med Chem 43:2731–2737 Pettit GR, Minardi MD, Rosenberg HJ, Hamel E, Bibby MC, Martin SW, Jung MK, Pettit RK, Cuthbertson TJ, Chapuis JC (2005) Antineoplastic agents. 509: synthesis of fluorcombstatin phosphate and related 3-halostilbenes. J Nat Prod 68:1450–1458 Pettit GR, Toki B, Herald DL, Verdier-Pinard P, Boyd MR, Hamel E, Pettit RK (1998) Synthesis of phenstatin phosphate1a. J Med Chem 41:1688–1695 Singh R, Kaur H (2009) Advances in synthetic approaches for the preparation of combretastatin-based anti-cancer agents. Synthesis 2009:2471–2491 Titov IY, Sagamanova IK, Gritsenko RT, Karmanova IB, Atamanenko OP, Semenova MN, Semenov VV (2011) Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues. Bioorg Med Chem Lett 21:1578–1581 Wang XJ, Zhang L, Byrne D, Nummy L, Weber D, Krishnamurthy D, Yee N, Senanayake CH (2014) Efficient synthesis of empagliflozin, an inhibitor of SGLT-2, utilizing an AlCl3-promoted silane reduction of a β-glycopyranoside. Org Lett 16:4090–4093 Wei RJ, Lin SS, Wu WR, Chen LR, Li CF, Chen HD, Chou CT, Chen YC, Liang SS, Chien ST (2016) A microtubule inhibitor, ABT-751, induces autophagy and delays apoptosis in Huh-7 cells. Toxicol Appl Pharm 311:88–98