Synthesis and evaluation of the antiproliferative activity of novel pyrrolo[1,2-a]quinoxaline derivatives, potential inhibitors of Akt kinase. Part II

References

• Hanahan Fabre D, Weinberg RA. The hallmarks of cancer. Cell 2000;100:57–70.
   PubMed Web of Science ®Google Scholar
• Sawyers C. Targeted cancer therapy. Nature 2004;432:294–7.
   PubMed Web of Science ®Google Scholar
• Li Q, Xu W. Novel anticancer targets and drug discovery in post genomic age. Curr Med Chem Anticancer Agents 2005;5:53–63.
   PubMedGoogle Scholar
• Franke TF. PI3K/Akt: getting it right matters. Oncogene 2008;27:6473–88.
   PubMed Web of Science ®Google Scholar
• Machajewski T, Xiaodong L, Jefferson AB, Zhenai G. Akt kinase and Hsp90 inhibitors as novel anti-cancer therapeutics. Annu Rep Med Chem 2005;40:263–76.
   Web of Science ®Google Scholar
• Barnett SF, Bilodeau MT, Lindsley CW. The Akt/PKB family of protein kinases: a review of small molecule inhibitors and progress towards target validation. Curr Top Med Chem 2005;5:109–25.
   PubMed Web of Science ®Google Scholar
• Cheng JQ, Lindsley CW, Cheng GZ, Yang H, Nicosia SV. The Akt/PKB pathway: molecular target for cancer drug discovery. Oncogene 2005;24:7482–92.
   PubMed Web of Science ®Google Scholar
• Lindsley CW, Zhao Z, Leister WH, Robinson RG, Barnett SF, Defeo-Jones D, et al. Allosteric Akt (PKB) inhibitors: discovery and SAR of isozyme selective inhibitors. Bioorg Med Chem Lett 2005;15:761–4.
   PubMed Web of Science ®Google Scholar
• Zhao Z, Leister WH, Robinson RG, Barnett SF, Defeo-Jones D, Jones RE, et al. Discovery of 2,3,5-trisubstituted pyridine derivatives as potent Akt1 and Akt2 dual inhibitors. Bioorg Med Chem Lett 2005;15:905–9.
   PubMed Web of Science ®Google Scholar
• Kumar CC, Madison V. AKT crystal structure and AKT-specific inhibitors. Oncogene 2005;24:7493–501.
   PubMed Web of Science ®Google Scholar
• Zhao Z, Robinson RG, Barnett SF, Defeo-Jones D, Jones RE, Hartman GD, et al. Development of potent, allosteric dual Akt1 and Akt2 inhibitors with improved physical properties and cell activity. Bioorg Med Chem Lett 2008;18:49–53.
   PubMed Web of Science ®Google Scholar
• Graff JR. Emerging targets in the AKT pathway for treatment of androgen-independent prostatic adenocarcinoma. Expert Opin Ther Targets 2002;6:103–13.
   PubMedGoogle Scholar
• Li Q, Zhu GD. Targeting serine/threonine protein kinase B/Akt and cell-cycle checkpoint kinases for treating cancer. Curr Top Med Chem 2002;2:939–71.
   PubMedGoogle Scholar
• Heerding DA, Safonov IG, Verma SK. Small molecule inhibitors of Akt/PKB kinase as a strategy for treating cancer. Annu Rep Med Chem 2007;42:365–76.
   Web of Science ®Google Scholar
• Hartnett JC, Barnett SF, Bilodeau MT, Defeo-Jones D, Hartman GD, Huber HE, et al. Optimization of 2,3,5-trisubstituted pyridine derivatives as potent allosteric Akt1 and Akt2 inhibitors. Bioorg Med Chem Lett 2008;18:2194–7.
   PubMed Web of Science ®Google Scholar
• Bilodeau MT, Balitza AE, Hoffman JM, Manley PJ, Barnett SF, Haskell K, et al. Allosteric inhibitors of Akt1 and Akt2: a naphthyridinone with efficacy in an A2780 tumor xenograft model. Bioorg Med Chem 2008;18:3178–82.
   Web of Science ®Google Scholar
• Wu Z, Hartnett JC, Neilson LA, Robinson RG, Fu S, Barnett SF, et al. Development of pyridopyrimidines as potent Akt1/2 inhibitors. Bioorg Med Chem 2008;18:1274–9.
   Web of Science ®Google Scholar
• Wu Z, Robinson RG, Fu S, Barnett SF, Defeo-Jones D, Jones RE, et al. Rapid assembly of diverse and potent allosteric Akt inhibitors. Bioorg Med Chem 2008;18:2211–14.
   Web of Science ®Google Scholar
• Desplat V, Geneste A, Begorre MA, Belisle Fabre S, 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;23:648–58.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Guillon J, Grellier P, Labaied M, Sonnet P, Léger J-M, 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.
   PubMed Web of Science ®Google Scholar
• Vidaillac C, Guillon J, Arpin C, Forfar-Bares I, Grellet J, Moreau S, et al. Synthesis of omeprazole analogues and evaluation of these as potential inhibitors of the multidrug efflux pump NorA of Staphylococcus aureus. Antimicrob Agents Chemother 2007;51:831–8.
   PubMed Web of Science ®Google Scholar
• Guillon J, Forfar I, Desplat V, Belisle Fabre S, 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;22:541–9.
   PubMed Web of Science ®Google Scholar
• Schann S, Mayer S, Gardan S. Pyrrolo[1,2-a]quinoxaline derivatives as Adenosine A3 receptor modulators and uses thereof. Eur Patent 2007, 1798233 A1. Chem Abstr 2007;147:72808.
   Google Scholar
• He Y, Yang J, Wu B, Robinson D, Sprankle K, Kung PP, et al. Synthesis and evaluation of novel bacterial rRNA-binding benzimidazoles by mass spectrometry. Bioorg Med Chem 2004;14:695–9.
   Web of Science ®Google Scholar
• Bergauer M, Gmeiner P. Traceless Linking of Pyrroles: General Methology and Solid Phase Supported Functionalizations. Synthesis 2002;2:274–8.
   Google Scholar
• Meyers KM, Mendez-Andino J, Colson AO, Hu XE, Wos JA, Mitchell MC, et al. Novel pyrazolopiperazinone- and pyrrolopiperazinone-based MCH-R1 antagonists. Bioorg Med Chem Lett 2007;17:657–61.
   PubMed Web of Science ®Google Scholar
• Handy ST, Bregman H, Lewis J, Zhang X, Zhang Y. An unusual dehalogenation in the Suzuki coupling of 4-bromopyrrole-2-carboxylates. Tetrahedron Lett 2003;44:427–30.
   Web of Science ®Google Scholar
• Handy ST, Zhang Y, Bregman H. A modular synthesis of the lamellarins: total synthesis of lamellarin G trimethyl ether. J Org Chem 2004;69:2362–6.
   PubMed Web of Science ®Google Scholar
• Smith JA, Ng S, White J. The regioselective synthesis of aryl pyrroles. Org Biomol Chem 2006;4:2477–82.
   PubMed Web of Science ®Google Scholar
• Miyaura N, Suzuki A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem Rev 1995;95:2457–83.
   Web of Science ®Google Scholar
• Barton DHR, Kervagoret J, Zard SZ. A useful synthesis of pyrroles from nitroolefins. Tetrahedron 1990;46:7587–98.
   Web of Science ®Google Scholar
• Dumoulin H, Rault S, Robba M. Synthesis of phenylpyrrolyl pyrroles. Part III. J Heterocyclic Chem 1997;34:13–16.
   Web of Science ®Google Scholar
• Chang CK, Bag N. Phenylpyrroles by Suzuki Cross Coupling and a Synthesis of Type I Tetramethyltetraphenylporphyrin. J Org Chem 1995;60:7030–2.
   Web of Science ®Google Scholar
• Zhang L, Meier W, Wats E, Costello TD, Ma P, Ensinger CL, et al. Pictet-Spengler reaction in trifluoroacetic acid. Large scale synthesis of pyridoindolobenzodiazepine as an atypical antipsychotic agent. Tetrahedron Lett 1995;36:8387–90.
   Web of Science ®Google Scholar
• Beach MJ, Hope R, Dieter HK, Rusell RK. Two Step Synthesis of Substituted Indolo[1,2-a]-Quinoxalin-6-Ones. Synth Commun 1995;25:2165–83.
   Web of Science ®Google Scholar
• Guillon J, Louchahi-Raoul J, Boulouard M, Dallemagne P, Daoust M, Rault S. Synthesis of new ethyl 4-[3-dimethylamino]propylmethylamino]pyrrolo[1,2-a]quinoxaline-2 carboxylate derivatives. Pharm Pharmacol Commun 1998;4:319–24.
   Google Scholar
• Supplementary X-ray crystallographic data of compounds 1b, 1dand 1e (CCDC-693149, CCDC-707577 and CCDC-693150): Cambridge Crystallographic Data Centre, University Chemical Laboratory, 12 Union Road, Cambridge, CB2 1EZ, UK.E-mail:[email protected].
   Google Scholar