Compounds, compositions, and methods of agelastatin alkaloids: patent evaluation of WO2015042239 (A1)

References

• D’Ambrosio M, Guerriero A, Debitus C, et al. Agelastatin A, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the Coral Sea. J Chem Soc Chem Commun. 1993;1305–1306.
   Google Scholar
• D’Ambrosio M, Guerriero A, Chiasera G, et al. Conformational preferences and absolute configuration of agelastatin A, a cytotoxic alkaloid of the axinellid sponge Agelas dendromorpha from the Coral Sea, via combined molecular modeling, NMR, and exciton splitting for diamide and hydroxyamide derivatives. Helv Chim Acta. 1994;77:1895–1902.
   Web of Science ®Google Scholar
• D’Ambrosio M, Guerriero A, Ripamonti M, et al. The active centers of agelastatin A, a strongly cytotoxic alkaloid of the Coral sea axinellid sponge Agelas dendromorpha, as determined by comparative bioassays with semisynthetic derivatives. Helv Chim Acta. 1996;79:727–735.
   Web of Science ®Google Scholar
• Pettit GR, Ducki S, Herald DL, et al. Antineoplastic agents 470. Absolute configuration of the marine sponge bromopyrrole agelastatin A. Oncol Res. 2005;15:11–20.
   PubMed Web of Science ®Google Scholar
• Hong TW, Jímenez DR, Molinski TF. Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A. J Nat Prod. 1998;61:158–161.
   PubMed Web of Science ®Google Scholar
• Tilvi S, Moriou C, Martin M, et al. Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge agelas dendromorpha. J Nat Prod. 2010;73:720–723.
   PubMed Web of Science ®Google Scholar
• Mason CK, McFarlane S, Johnston PG, et al. Agelastatin A: a novel inhibitor of osteopontin-mediated adhesion, invasion, and colony formation. Mol Cancer Ther. 2008;7:548–558.
   PubMed Web of Science ®Google Scholar
• El-Tanani MK, Hale KJ, Manaviazar S, et al. (-)-Agelastatin A and agelastatin analogs as medicaments in treatment of metastatic disease. PCT Int Appl. 2008. WO 2008078109 A2 20080703.
   Google Scholar
• Hale KJ, Domostoj MM, El-Tanani M, et al. Total synthesis and mechanism of action studies on the antitumor alkaloid, (-)-agelastatin A. In: Harmata M. editor. Strategies and tactics in organic synthesis. Vol. 6, London: Elsevier academic press; 2005. Chapter 11. p. 352–394.
   Google Scholar
• Hale KJ, Domostoj MM, Irving E, et al. Preparation of analogues of the agelastatin family of antitumour and GSK-3β-inhibiting alkaloids. PCT Int Appl. 2004. WO 2004106343 A2 20041209.
   Google Scholar
• Li Z, Shigeoka D, Caulfield TR, et al. An integrated approach to the discovery of potent agelastatin A analogues for brain tumors: chemical synthesis and biological, physicochemical and CNS pharmacokinetic analyses. Med Chem Commun. 2013;4:1093–1098.
   Web of Science ®Google Scholar
• Stout EP, Choi MY, Castro JE, et al. Potent fluorinated agelastatin Analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies. J Med Chem. 2014;57:5085–5093.
   PubMed Web of Science ®Google Scholar
• Jouanneau M, McClary B, Reyes J, et al. Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe. Bioorg Med Chem Lett. 2016;26:2092–2097.
   PubMed Web of Science ®Google Scholar
• Tun HW, Yoshimitsu T, Shigeoka D, et al. Treating brain cancer using agelastatin A and analogues thereof. PCT Int Appl. 2014. WO 2014059314 A1 20140417. IMIDAZO[4ʹ,5ʹ:4,5]CYCLOPENTA[1,2-e]PYRROLO[1,2-a]PYRAZINES and OXAZOLO[4ʹ,5ʹ:4,5]CYCLOPENTA[1,2-e]PYRROLO[1,2-a]PYRAZINES FOR TREATING BRAIN CANCER”) (PCT/US2013/064605; approval date 6/7/2016).
   Google Scholar
• Li Z, Kamon T, Personett DA, et al. Pharmacokinetics of Agelastatin A in the central nervous system. Med Chem Commun. 2012;3:233–237.
   Web of Science ®Google Scholar
• Han S, Siegel DS, Morrison KC, et al. Synthesis and anticancer activity of all known (-)-Agelastatin alkaloids. J Org Chem. 2013;78:11970–11984.
   PubMed Web of Science ®Google Scholar
• Movassaghi M, Siegel DS, Han S. Total synthesis of all (-)-agelastatin alkaloids. Chem Sci. 2010;1:561–566.
   PubMed Web of Science ®Google Scholar
• Stien D, Anderson GT, Chase CE, et al. Total synthesis of the antitumor marine sponge alkaloid agelastatin A. J Am Chem Soc. 1999;121:9574–9579.
   Web of Science ®Google Scholar
• Feldman KS, Saunders JC. Alkynyliodonium salts in organic synthesis. application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B. J Am Chem Soc. 2002;124:9060–9061.
   PubMed Web of Science ®Google Scholar
• Feldman KS, Saunders JC, Wrobleski ML. Alkynyliodonium salts in organic synthesis. development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B. J Org Chem. 2002;67:7096–7109.
   PubMed Web of Science ®Google Scholar
• Hale KJ, Domostoj MM, Tocher DA, et al. Enantiospecific formal total synthesis of the tumor and GSK-3b inhibiting alkaloid, (-)-agelastatin A. Org Lett. 2003;5:2927–2930.
   PubMed Web of Science ®Google Scholar
• Domostoj MM, Irving E, Scheinmann F, et al. New total synthesis of the marine antitumor alkaloid (-)-agelastatin A. Org Lett. 2004;6:2615–2618.
   PubMed Web of Science ®Google Scholar
• Davis FA, Deng J. Asymmetric total synthesis of (-)-agelastatin A using sulfinimine (N-sulfinyl imine) derived methodologies. Org Lett. 2005;7:621–623.
   PubMed Web of Science ®Google Scholar
• Trost BM, Dong G. New class of nucleophiles for palladium-catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A. J Am Chem Soc. 2006;128:6054–6055.
   PubMed Web of Science ®Google Scholar
• Davis FA, Deng J. Asymmetric synthesis of (-)-agelastatin A. PCT Int Appl. 2006. WO 2006055578 A2 20060526.
   Google Scholar
• Ichikawa Y, Yamaoka T, Nakano K, et al. Synthesis of (-)-agelastatin A by [3.3] sigmatropic rearrangement of allyl cyanate. Org Lett. 2007;9:2989–2992.
   PubMed Web of Science ®Google Scholar
• Yoshimitsu T, Ino T, Tanaka T. Total Ssynthesis of (-)-agelastatin A. Org Lett. 2008;10:5457–5460.
   PubMed Web of Science ®Google Scholar
• Dickson PD, Wardrop DJ. Total synthesis of (±)-agelastatin A, a potent inhibitor of osteopontin-mediated neoplastic transformations. Org Lett. 2009;11:1341–1344.
   PubMed Web of Science ®Google Scholar
• Hama N, Matsuda T, Sato T, et al. Total synthesis of (-)-agelastatin A: the application of a sequential sigmatropic rearrangement. Org Lett. 2009;11:2687–2690.
   PubMed Web of Science ®Google Scholar
• Wehn PM, Du Bois J. A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A. Angew Chem Int Ed. 2009;48:3802–3805.
   PubMed Web of Science ®Google Scholar
• Davis FA, Zhang Y, Qiu H. Improved synthesis of (-)-agelastatin A. Synth Commun. 2009;39:1914–1919.
   Web of Science ®Google Scholar
• Trost BM, Dong G. A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: agelastatin A. Chem Eur J. 2009;15:6910–6919.
   PubMed Web of Science ®Google Scholar
• Yoshimitsu T, Ino T, Futamura N, et al. Total synthesis of the β-catenin inhibitor, (-)-agelastatin A: a second-generation approach based on radical aminobromination. Org Lett. 2009;11:3402–3405.
   PubMed Web of Science ®Google Scholar
• Menjo Y, Hamajima A, Sasaki N, et al. Asymmetric aziridination of cyclic enones using chiral diamine catalysts and its application to the total synthesis of (-)-agelastatin A. Org Lett. 2011;13:5744–5747.
   PubMed Web of Science ®Google Scholar
• Kano T, Sakamoto R, Akakura M, et al. Stereocontrolled synthesis of vicinal diamines by organocatalytic asymmetric Mannich reaction of N-protected aminoacetaldehydes: formal synthesis of (-)-agelastatin A. J Am Chem Soc. 2012;134:7516–7520.
   PubMed Web of Science ®Google Scholar
• Reyes JP, Romo D. Bioinspired total synthesis of agelastatin A. Angew Chem Int Ed. 2012;51:6870–6873.
   PubMed Web of Science ®Google Scholar
• Duspara PA, Batey RA. A short total synthesis of the marine sponge pyrrole-2-aminoimidazole alkaloid (±)-agelastatin A. Angew Chem Int Ed. 2013;52:10862–10866.
   PubMed Web of Science ®Google Scholar
• Shigeoka D, Kamon T, Yoshimitsu T. Formal synthesis of (-)-agelastatin A: an iron(II)-mediated cyclization strategy. Beilstein J Org Chem. 2013;9:860–865.
   PubMed Web of Science ®Google Scholar
• Dong G. Recent advances in the total synthesis of agelastatins. Pure Appl Chem. 2010;82(12):2231–2246.
   Web of Science ®Google Scholar
• Jacquot DEN, Lindel T. Challenge palau’amine: current standings. Curr Org Chem. 2005;9:1551–1565.
   Web of Science ®Google Scholar
• Yamaoka T, Ichikawa Y, Kotsuki H. Synthesis of marine natural product agelastatin A. J Synth Org Chem Jpn. 2012;70(6):615–628.
   Web of Science ®Google Scholar
• Crossley SWM, Shenvi RA. A longitudinal study of alkaloid synthesis reveals functional group interconversions as bad actors. Chem Rev. 2015;115:9465–9531.
   PubMed Web of Science ®Google Scholar
• Swerdlow SH, Campo E, Harris NL, et al. WHO classification of tumours of haematopoietic and lymphoid tissues. 4th ed. Lyon, France: IARC Press; 2008.
   Google Scholar