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Original Article

Synthesis and evaluation of the antiproliferative activity of novel isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives

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Pages 657-667 | Received 05 Jan 2010, Accepted 12 Dec 2010, Published online: 21 Jan 2011

References

  • Campiani G, Butini S, Fattorusso C, Trotta F, Franceschina S, De Angelis M, Nielsen KS. Novel aryl piperazine derivatives with medical utility. 2006, WO2006072608.
  • Campiani G, Aiello F, Fabbrini M, Morelli E, Ramunno A, Armaroli S et al. Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent. J Med Chem 2001;44:305–315.
  • Schann S, Mayer S, Gardan S. Pyrrolo[1,2-a]quinoxaline derivatives as Adenosine A3 receptor modulators and uses thereof. 2007, EP1798233.
  • Guillon J, Grellier P, Labaied M, Sonnet P, Léger JM, Déprez-Poulain R et al. Synthesis, antimalarial activity, and molecular modeling of new pyrrolo[1,2-a]quinoxalines, bispyrrolo[1,2-a]quinoxalines, bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and bispyrrolo[1,2-a]thieno[3,2-e]pyrazines. J Med Chem 2004;47:1997–2009.
  • Guillon J, Forfar I, Mamani-Matsuda M, Desplat V, Saliège M, Thiolat D et al. Synthesis, analytical behaviour and biological evaluation of new 4-substituted pyrrolo[1,2-a]quinoxalines as antileishmanial agents. Bioorg Med Chem 2007;15:194–210.
  • Guillon J, Forfar I, Desplat V, Fabre SB, Thiolat D, Massip S et al. Synthesis of new 4-(E)-alkenylpyrrolo[1,2-a]quinoxalines as antileishmanial agents by Suzuki-Miyaura cross-coupling reactions. J Enzyme Inhib Med Chem 2007;22:541–549.
  • Guillon J, Moreau S, Mouray E, Sinou V, Forfar I, Fabre SB et al. New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: synthesis, and in vitro antimalarial activity. Bioorg Med Chem 2008;16:9133–9144.
  • Milne J, Normington KD, Milburn M. Tetrahydroquinoxalinone sirtuin modulators. 2006, WO2006094210.
  • Grande F, Aiello F, Grazia OD, Brizzi A, Garofalo A, Neamati N. Synthesis and antitumor activities of a series of novel quinoxalinhydrazides. Bioorg Med Chem 2007;15:288–294.
  • Desplat V, Geneste A, Begorre MA, Fabre SB, Brajot S, Massip S et al. Synthesis of new pyrrolo[1,2-a]quinoxaline derivatives as potential inhibitors of Akt kinase. J Enzyme Inhib Med Chem 2008;23:648–658.
  • Desplat V, Moreau S, Gay A, Fabre SB, Thiolat D, Massip S et al. Synthesis and evaluation of the antiproliferative activity of novel pyrrolo[1,2-a]quinoxaline derivatives, potential inhibitors of Akt kinase. Part II. J Enzyme Inhib Med Chem 2010;25:204–215.
  • Wermuth CG. Ring transformations. In: Wermuth CG, ed. The Practice of Medicinal Chemistry. Amsterdam: Elsevier Netherland; 2003. P 215–231.
  • Beach MJ, Hope R, Dieter HK, Rusell RK. Two step synthesis of substituted indolo[1,2-a]-quinoxalin-6-ones. Synth Commun 1995;25:2165–2183.
  • May DA, Lash TD. Porphyrins with exocyclic rings. 2. Synthesis of geochemically significant tetrahydrobenzoporphyrins from 4,5,6,7-tetrahydro-2H-isoindoles. J Org Chem 1992;57:4820–4828.
  • Finikova OS, Cheprakov AV, Beletskaya IP, Carroll PJ, Vinogradov SA. Novel versatile synthesis of substituted tetrabenzoporphyrins. J Org Chem 2004;69:522–535.
  • Ono N, Hironaga H, Ono K, Kaneko S, Murashima T, Ueda T, Tsukamura C, Ogawa T. A new synthesis of pyrroles and porphyrins fused with aromatic rings. J Chem Soc, Perkin Trans 1 1996;5:417–423.
  • Jew SS, Kim HD, Cho YS, Cook CH. A practical preparations of conjugated nitroalkenes. Chem Lett 1986;15:1747–1748.
  • Yuan Q, Ma D. A one-pot coupling/hydrolysis/condensation process to pyrrolo[1,2-a]quinoxaline. J Org Chem 2008;73:5159–5162.
  • Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 1995;95:2457–2483.
  • Supplementary X-ray crystallographic data of compounds 1a and 1c (CCDC-746052 and CCDC-746053): Cambridge Crystallographic Data Centre, University Chemical Lab, 12 Union Road, Cambridge, CB2 1EZ, U.K.; E-mail: [email protected].
  • Diana P, Martorana A, Barraja P, Montalbano A, Dattolo G, Cirrincione G et al. Isoindolo[2,1-a]quinoxaline derivatives, novel potent antitumor agents with dual inhibition of tubulin polymerization and topoisomerase I. J Med Chem 2008;51:2387–2399.
  • Diana P, Martorana A, Barraja P, Lauria A, Montalbano A, Almerico AM et al. Isoindolo[2,1-c]benzo[1,2,4]triazines: a new ring system with antiproliferative activity. Bioorg Med Chem 2007;15:343–349.
  • Paolini JP, Palopoli FP, Lendvay LJ, Huffman J. Pyrido[2′1′:2,3]imidazo[4,5-c]isoquinoline and the alkylation of pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one. J Heterocyclic Chem 1987;24:549–553.
  • Campiani G, Nacci V, Corelli F, Anzini M. Polycondensed heterocycles. VII. A convenient synthesis of pyrrolo[1,2-a]quinoxaline derivatives by intramolecular aromatic nucleophilic displacement. Synth Commun 1991;21:1567–1576.
  • Cailly T, Fabis F, Rault S. A new, direct, and efficient synthesis of benzonaphthyridin-5-ones. Tetrahedron 2006;62:5862–5867.
  • Cailly T, Fabis F, Legay R, Oulyadi H, Rault S. The synthesis of three new heterocycles: the pyrido[4,3 or 3,4 or 2,3-c]-1,5-naphthyridines. Tetrahedron 2007;63:71–76.
  • Dubost E, Magnelli R, Cailly T, Legay R, Fabis F, Rault S. General method for the synthesis of substituted phenanthridin-6(5H)-ones using a KOH-mediated anionic ring closure as the key step. Tetrahedron 2010;66:5008–5016.
  • Liu P, Xu B, Li J, Lu H. LY294002 inhibits leukemia cell invasion and migration through early growth response gene 1 induction independent of phosphatidylinositol 3-kinase-Akt pathway. Biochem Biophys Res Commun 2008;377:187–190.
  • Moon DO, Park C, Heo MS, Park YM, Choi YH, Kim GY. PD98059 triggers G1 arrest and apoptosis in human leukemic U937 cells through downregulation of Akt signal pathway. Int Immunopharmacol 2007;7:36–45.
  • Jørgensen HG, Allan EK, Graham SM, Godden JL, Richmond L, Elliott MA et al. Lonafarnib reduces the resistance of primitive quiescent CML cells to imatinib mesylate in vitro. Leukemia 2005;19:1184–1191.
  • Zhao S, Konopleva M, Cabreira-Hansen M, Xie Z, Hu W, Milella M et al. Inhibition of phosphatidylinositol 3-kinase dephosphorylates BAD and promotes apoptosis in myeloid leukemias. Leukemia 2004;18:267–275.

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