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Articles

Synthesis of 1′-Aryl-1,3′-bi-β-carbolines and Their Saturated Counterparts

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Pages 131-140 | Received 17 Nov 2015, Accepted 25 Mar 2016, Published online: 28 Nov 2016

References

  • Torreilles, J., M.-C. Guérin, and A. Previero. “Des Structures Simples Aux Potentialités Pharmacologiques élevées: Les β-carbolines. Origines, Syntheses, Propriétés Biologiques.” Biochimie 67 (1985): 929–47.
  • Love, B. E. “Synthesis of β-carbolines. A Review.” Organic Preparations and Procedures International 28 (1996): 1–64.
  • McNulty, J., and I. W. J. Still. “Synthetic Approaches to the Eudistomin Marine Alkaloids.” Current Organic Chemistry 4 (2000): 121–38.
  • Rosillo, M., A. González-Gómez, G. Domínguez, and J. Pérez-Castells. “Chemistry of Biologically Active β-carbolines.” Targets in Heterocyclic Chemistry 12 (2008): 212–57.
  • Domínguez, G., and J. Pérez-Castells. “Chemistry of β-carbolines as Synthetic Intermediates.” European Journal of Organic Chemistry (2011): 7243–53.
  • Singh, V., and S. Batra. “1-Formyl-9H-β-carboline: A Useful Scaffold for Synthesizing Substituted- and Fused-β-carbolines.” Current Organic Synthesis 9 (2012): 513–28.
  • Allen, J. R. F., and B. R. Holmstedt. “The simple β-carboline alkaloids.” Phytochemistry 19 (1980): 1573–82.
  • Greube, A., and H. Rommelspacher. “Isolation and Identifications of Two [3H]norharman-([3H]β-carboline)-binding Proteins from Rat Liver.” Journal of Chromatography B 784 (2003): 155–68.
  • Medina, J. H., M. L. de Stein, and E. D. Robertis. “n-[3H]Butyl-β-carboline-3-carboxylate, A Putative Endogenous Ligand, Binds Preferentially to Subtype 1 of Central Benzodiazepine Receptors.” Journal of Neurochemistry 52 (1989): 665–70.
  • Takahashi, Y., T. Kubota, J. Fromont, and J. Kobayashi. “Zamamidines A and B, New Manzamine Alkaloids From the Sponge Amphimedon Species.” Organic Letters 11 (2009): 21–4.
  • He, W.-F., D.-Q. Xue, L.-G. Yao, J.-Y. Li, J. Li, and Y.-W. Guo. “Hainanerectamines A–C, Alkaloids from the Hainan Sponge Hyrtois Erecta.” Marine Drugs 12 (2014): 3982–93.
  • Herraiz, T., and E. Papavergou. “Identification and Occurrence of Tryptamine- and Tryptophan-Derived Tetrahydro-β-carbolines in Commercial Sausages.” Journal of Agricultural and Food Chemistry 52 (2004): 2652–58.
  • Alves, R. C., S. Casal, and B. P. P. Oliveira. “Factors Influencing the Norharman and Harman Contents in Espresso Coffee.” Journal of Agricultural and Food Chemistry 55 (2007): 1832–38.
  • Cao, R., W. Peng, Z. Wang, and A. Xu. “β-Carboline Alkaloids: Biochemical and Pharmacological Functions.” Current Medicinal Chemistry 14 (2007): 479–500.
  • Laine, A. E., C. Lood, and A. M. P. Koskinen. “Pharmacological Importance of Optically Active Tetrahydro-β-carboline and Synthetic Approaches to Create the C1 Stereocenter.” Molecules 19 (2014): 1544–67.
  • Xiao, S., W. Lin, C. Wang, and M. Yang. “Synthesis and Biological Evaluation of DNA Targeting Flexible Side-chain Substituted β-carboline Derivatives.” Bioorganic & Medicinal Chemistry Letters 11 (2001): 437–41.
  • Deveau, A. M., M. A. Labroli, C. M. Dieckhaus, M. T. Barthen, K. S. Smith, and T. L. Macdonald. “The Synthesis of Amino Acid-functionalized β-carbolines as Topoisomerase II Inhibitors.” Bioorganic & Medicinal Chemistry Letters 11 (2001): 1251–55.
  • Li, Y., F. Liang, W. Jiang, F. Yu, R. Cao, Q. Ma, X. Dai, J. Jiang, Y. Wang, and S. Si. “DH334, a β-carboline Anti-cancer Drug, Inhibits the CDK Activity of Budding Yeast.” Cancer Biology & Therapy 6 (2007): 1204–10.
  • Castro, A. C., L. C. Dang, F. Soucy, L. Grenier, H. Mazdiyasni, M. Hottelet, L. Parent, C. Pien, V. Palombella, and J. Adams. “Novel IKK Inhibitors: β-carbolines” Bioorganic & Medicinal Chemistry Letters 13 (2003): 2419–22.
  • Trujillo, J. I., M. J. Meyers, D. R. Anderson, S. Hegde, M. W. Mahoney, W. F. Vernier, I. P. Buchler, K. K. Wu, S. Yang, S. J. Hartmann, and D. B. Reitz. “Novel Tetrahydro-β-carboline-1-carboxylic Acids as Inhibitors of Mitogen Activated Protein Kinase-Activated Protein Kinase 2 (MK-2).” Bioorganic & Medicinal Chemistry Letters 17 (2007): 4657–63.
  • Barsanti, P. A., W. Wang, Z. Ni, D. Duhl, N. Brammeier, E. Martin, O. Bussiere, and A. O. Walter. “The Discovery of Tetrahydro-β-carbolines as Inhibitors of the Kinesin Eg5.” Bioorganic & Medicinal Chemistry Letters 20 (2010): 157–60.
  • Cao, R., W. Peng, H. Chen, X. Hou, H. Guan, Q. Chen, Y. Ma, and A. Xu. “Synthesis and In Vitro Cytotoxic Evaluation of 1,3-disubstituted and 1,3,9-trisubstituted β-carboline Derivatives.” European Journal of Medicinal Chemistry 40 (2005): 249–57.
  • Guan, H., H. Chen, W. Peng, Y. Ma, R. Cao, X. Liu, and A. Xu. “Design of β-carboline Derivatives as DNA-targeting Antitumor Agents.” European Journal of Medicinal Chemistry 41 (2006): 1167–79.
  • Chen, Z., R. Cao, B. Shi, W. Yi, L. Yu, H. Song, and Z. Ren. “Synthesis and Biological Evaluation of Novel β-carbolines as Potent Cytotoxic and DNA Interacting Agents.” Chemical & Pharmaceutical Bulletin 58 (2010): 901–7.
  • Kamal, A., M. P. N. Rao, P. Swapna, V. Srinivasulu, C. Bagul, A. B. Shaik, K. Mullagiri, J. Kovvuri, V. S. Reddy, K. Vidyasagar, and N. Nagesh. “Synthesis of β-carboline-benzimidazole Conjugates Using Lanthanum Nitrate as a Catalyst and Their Biological Evaluation.” Organic & Biomolecular Chemistry 12 (2014): 2370–87.
  • Jiao, W.-H., H. Gao, C.-Y. Li, F. Zhao, R.-W. Jiang, Y. Wang, G.-X. Zhou, and X.-S. Yao. ”Quassidines A–D, bis-β-Carboline Alkaloids from the Stems of Picrasma quassioides.” Journal of Natural Products 73 (2010): 167–71.
  • Jiao, W.-H., H. Gao, F. Zhao, H.-W. Lin, Y.-M. Pan, G.-X. Zhou, and X.-S. Yao. “Anti-inflammatory Alkaloids from the Stems of Picrasma Quassioides BENNET.” Chemical & Pharmaceutical Bulletin 59 (2011): 359–64.
  • Wang, K.-B., Y.-T. Di, Y. Bao, C.-M. Yuan, G. Chen, D.-H. Li, J. Bai, H.-P. He, X.-J. Hao, Y.-H. Pei, Y.-K. Jing, Z.-L. Li, and H.-M. Hua. “Peganumine A, a β-carboline Dimer with a New Octacyclic Scaffold from Peganum harmala.” Organic Letters 16 (2014): 4028–31.
  • Bai, B., L. Shen, J. Ren, and H.-J. Zhu. “Chiral Biscarboline N,N’-dioxide Derivatives: Highly Enantioselective Addition of Allyltrichlorosilane to Aldehydes.” Advanced Synthesis & Catalysis 354 (2012): 354–8.
  • Bai, B., H.-J. Zhu, and W. Pan. “Structure Influence of Chiral 1,1′-biscarboline-N,N’-dioxide on the Enantioselective Allylation of Aldehydes with Allyltrichloro Silanes.” Tetrahedron 68 (2012): 6829–36.
  • Ábrányi-Balogh, P., A. Dancsó, D. Frigyes, B. Volk, G. Keglevich, and M. Milen. “Convenient Synthesis of 1-aryl-9H-β-carboline-3-carbaldehydes and their Transformation into Dihydropyrimidinone Derivatives by Biginelli Reaction.” Tetrahedron 70 (2014): 5711–19.
  • Hazai, L., M. Milen, P. Kolonits, A. Dobó, and C. Szántay. “Preferred Carbon vs. Nitrogen Sulfonylation on β-carbolines.” Synthetic Communications 31 (2001): 919–27.
  • Milen, M., L. Hazai, P. Kolonits, Á. Gömöry, C. Szánty, and J. Fekete. “Preparation and Separation of 1-methyl-1,2,3,4-tetrahydro-β-carboline Enantiomers by HPLC Using a New Derivatization Reagent.” Journal of Liquid Chromatography & Related Technologies 27 (2004): 2921–33.
  • Milen, M., L. Hazai, P. Kolonits, G. Kalaus, L. Szabó, Á. Gömöry, and C. Szántay. “Studies on Stereoselective Approaches to β-carboline Derivatives.” Central European Journal of Chemistry 3 (2005): 118–36.
  • Milen, M., P. Ábrányi-Balogh, A. Dancsó, G. Simig, and G. Keglevich. “Reaction of 3,4-dihydro-β-carboline with 4-fluorophenyl-Nitrile Oxide.” Letters in Organic Chemistry 7 (2010): 377–82.
  • Milen, M., P. Ábrányi-Balogh, Z. Mucsi, A. Dancsó, D. Frigyes, L. Pongó, and G. Keglevich. “Synthesis of New β-carboline Derivatives Fused with β-lactam Rings. An Experimental and Theoretical Study.” Current Organic Chemistry 17 (2013): 1894–902.
  • Ábrányi-Balogh, P., Z. Mucsi, I. G. Csizmadia, A. Dancsó, G. Keglevich, and M. Milen. “Heteroatom Effect on Potential Energy Topology. A Novel Reaction Mechanism of Stereospecific Staudinger Synthesis.” Tetrahedron 70 (2014): 9682–94.
  • Milen, M., P. Slégel, P. Keglevich, G. Keglevich, G. Simig, and B. Volk. “Efficient Synthesis of Nb-thiacyltryptamine Derivatives by a Three-component Willgerodt-Kindler Reaction, and their Transformation to 1-substituted-3,4-dihydro-β-Carbolines.” Tetrahedron Letters 56 (2015): 5697–700.
  • Daugan, A., P. Grondin, C. Ruault, A.-C. M. de Gouville, H. Coste, J. Kirilovsky, F. Hyafil, and R. Labaudinière. “The Discovery of Tadalafil: A Novel and Highly Selective PDE 5 Inhibitor. 1:5,6,11,11a-Tetrahydro-1H-imidazo[1′,5′:1,6′pyrido[3,4-b]indole-1,3(2H)-dione Analogues.” Journal of Medicinal Chemistry 46 (2003): 4525–32.
  • Dantale, S. W., and B. C. G. Söderberg. “A Novel Palladium-catalyzed Synthesis of β-carbolines: Application in Total Synthesis of Naturally Occurring Alkaloids.” Tetrahedron 59 (2003): 5507–14.
  • Cain, M., R. W. Weber, F. Guzman, J. M. Cook, S. A. Barker, K. C. Rice, J. N. Crawley, S. M. Paul, and P. Skolnick. “β-Carbolines: Synthesis and Neurochemical and Pharmacological Actions on Brain Benzodiazepine Receptors.” Journal of Medicinal Chemistry 25 (1982): 1081–91.
  • Gessner, W. P., and A. Brossi. “β-Carbolines from Japanese Sake and Soy Sauce. Synthesis and Biological Activity of Flazine and Yellow Substance YS (perlolyrine).” Archiv der Pharmazie 321 (1988): 95–8.
  • Panarese, J. D., and S. P. Waters. “Room-temperature Aromatization of Tetrahydro-β-carbolines by 2-Iodoxybenzoic Acid: Utility in a Total Synthesis of Eudistomin U.” Organic Letters 12 (2010): 4086–9.

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