A facile synthesis and antibacterial activity of novel pyrrolo[3,4-b]quinolin-2(3H)-yl)benzamides

References

• Sangani, C.B.; Makawana, J.A.; Zhang, X.; Teraiya, S.B.; Lin, L.; Zhu, H.-L. Design, Synthesis and Molecular Modeling of Pyrazole–Quinoline–Pyridine Hybrids as a New Class of Antimicrobial and Anticancer Agents. Eur. J. Med. Chem. 2014, 76, 549–557. doi: 10.1016/j.ejmech.2014.01.018
   PubMed Web of Science ®Google Scholar
• Fernández, J.; Bert, F.; Nicolas-Chanoine, M.-H. The Challenges of Multi-drug-resistance in Hepatology. J. Hepatol. 2016, 65 (5), 1043–1054. doi: 10.1016/j.jhep.2016.08.006
   PubMed Web of Science ®Google Scholar
• Viegas-Junior, C.; Danuello, A.; Bolzani, V.D.; Barreir, E.J.; Fraga, C.A.M. Molecular Hybridization: A Useful Tool in the Design of New Drug Prototypes. Curr. Med. Chem. 2007, 14 (17), 1829–1852. doi: 10.2174/092986707781058805
   PubMed Web of Science ®Google Scholar
• Keri, R.S.; Patil, S.A. Quinoline: A Promising Antitubercular Target. Biomed. Pharmacother. 2014, 68 (8), 1161–1175. doi: 10.1016/j.biopha.2014.10.007
   PubMed Web of Science ®Google Scholar
• Simoes, J.B.; de Fatima, A.; Sabino, A.A.; Almeida Barbosa, L.C.; Fernandes, S.A. Efficient Synthesis of 2,4-Disubstituted Quinolines: Calix[n]arene-catalyzed Povarov-hydrogen-transfer Reaction Cascade. RSC Adv. 2014, 4 (36), 18612–18615. doi: 10.1039/C4RA02036G
   Web of Science ®Google Scholar
• Li, H.; Wang, C.; Huang, H.; Xu, X.; Li, Y. Silver-catalyzed Cascade Reaction of o-aminoaryl Compounds with Alkynes: An Aniline Mediated Synthesis of 2-substituted Quinolines. Tetrahedron Lett. 2011, 52 (10), 1108–1111. doi: 10.1016/j.tetlet.2010.12.102
   Web of Science ®Google Scholar
• Walsh, C.T.; Garneau-Tsodikova, S.; Howard-Jones, A.R. Biological Formation of Pyrroles: Nature’s Logic and Enzymatic Machinery. Nat. Prod. Rep. 2006, 23 (4), 517–531. doi: 10.1039/b605245m
   PubMed Web of Science ®Google Scholar
• Young, I.S.; Thornton, P.D.; Thompson, A. Synthesis of Natural Products Containing the Pyrrolic Ring. Nat. Prod. Rep. 2010, 27 (12), 1801–1839. doi: 10.1039/c0np00014k
   PubMed Web of Science ®Google Scholar
• Fan, H.; Peng, J.; Hamann, M.T.; Hu, J.-F. Lamellarins and Related Pyrrole-derived Alkaloids from Marine Organisms. Chem. Rev. 2008, 108 (1), 264–287. doi: 10.1021/cr078199m
   PubMed Web of Science ®Google Scholar
• Fukuda, T.; Ishibashi, F.; Iwao, M. Synthesis and Biological Activity of Lamellarin Alkaloids: An Overview. Heterocycles. 2011, 83 (3), 491–529. doi: 10.3987/REV-10-686
   Web of Science ®Google Scholar
• Nesterova, I.N.; Alekseeva, L.M.; Andreeva, N.I.; Golovina, S.M.; Granik, V.G. Synthesis and Study the Pharmacological Activity of Derivatives of 5-dimethylaminopyrano[3,2-c]quinolin-2-ones. Pharm. Chem. J. 1995, 29 (2), 111–114. doi: 10.1007/BF02226521
   Google Scholar
• Yamada, N.; Kadowaki, S.; Takahashi, K.; Umezu, K. MY-1250, a Major Metabolite of the Anti-allergic Drug Repirinast, Induces Phosphorylation of a 78-kDa Protein in Rat Mast Cells. Biochem. Pharmacol. 1992, 44 (6), 1211–1213. doi: 10.1016/0006-2952(92)90387-X
   PubMed Web of Science ®Google Scholar
• Faber, K.; StÚckler, H.; Kappe, T. Non-steroidal Antiinflammatory Agents. 1. Synthesis of 4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl Alkanoic Acids by the Wittig Reaction of Quinisatines. J. Heterocyclic Chem. 1984, 21 (4), 1177–1181. doi: 10.1002/jhet.5570210450
   Web of Science ®Google Scholar
• Akhmed Khodzhaeva, K.S.; Bessonova, I.A. Dokl. Akad. Nauk Uzh. SSR1982, 34–36 (Russ);Chem. Abstr. 1983, 98, 83727q. Dokl. Akad. Nauk Uzh. SSR1982, 34–36.
   Google Scholar
• Fortunak, J.M.D.; Mastrocola, A.R.; Mellinger, M.; Sisti, N.J.; Wood, J.L.; Zhuang, Z.-P. Novel Syntheses of Camptothecin Alkaloids, Part I. Intramolecular [4+2] Cycloadditions of N-arylimidates and 4H-3,1-benzoxazin-4-ones as 2-aza-1,3-dienes. Tetrahedron Lett. 1996, 37 (32), 5679–5682. doi: 10.1016/0040-4039(96)01204-X
   Web of Science ®Google Scholar
• Yadav, J.S.; Sarkar, S.; Chandrasekhar, S. A Convergent Total Synthesis of Mappicine Ketone: A Leading Antiviral Compound. Tetrahedron. 1999, 55 (17), 5449–5456. doi: 10.1016/S0040-4020(99)00191-X
   Web of Science ®Google Scholar
• Machtey, V.; Gottlieb, H.E.; Byk, G. Total Synthesis of Structures Proposed for Quinocitrinines A and B and their Analogs. Microwave Energy as Efficient Tool for Generating Heterocycles. Arkivoc. 2011,U308–U479.
   Google Scholar
• Wang, H.; Ganesan, A. Total Synthesis of the Cytotoxic Alkaloid Luotonin A. Tetrahedron Lett. 1998, 39 (49), 9097–9098. doi: 10.1016/S0040-4039(98)02004-8
   Web of Science ®Google Scholar
• Van Es, T.; Staskun, B.; Van Vuuren, S. Sulphur-substituted Pyrrolo[3, 4-b]Quinolines: Synthesis, Chemistry and Antimicrobial Activity. S. Afr. J. Chem. 2005, 58, 74–81.
   Web of Science ®Google Scholar
• Sorokina, I.K.; Alekseeva, L.M.; Parshin, V.A.; Granik, V.G. Functional Derivatives of Tetramic Acid: New Approaches to the Synthesis of Heterotricyclic Compounds. Pharm. Chem. J. 2007, 41 (10), 543–548. doi: 10.1007/s11094-008-0009-x
   Google Scholar
• Ramaprasad, G.C.; Kalluraya, B.; Sunil Kumar, B.; Mallya, S. Synthesis of New Oxadiazole Derivatives as Anti-inflammatory, Analgesic, and Antimicrobial Agents. Med. Chem. Res. 2013, 22 (11), 5381–5389. doi: 10.1007/s00044-012-0298-1
   Web of Science ®Google Scholar
• Nagarapu, L.; Gaikwad, H.K.; Bantu, R.; Manikonda, S.R.; Ganesh Kumar, C.; Pombala, S. Lewis Acid-assisted Olefin Cross-metathesis Reaction: An Efficient Approach for the Synthesis of Glycosidic-pyrroloquinolinone Based Novel Building Blocks of Camptothecin and Evaluation of their Antitumor Activity. Tetrahedron Lett. 2012, 53 (10), 1287–1291. doi: 10.1016/j.tetlet.2012.01.001
   Web of Science ®Google Scholar
• Nagarapu, L.; Gaikwad, H.K.; Bantu, R.; Manikonda, S.R. Chemoenzymatic Synthesis with Lipase Catalyzed Resolution and Evaluation of Antitumor Activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one. Eur. J. Med. Chem. 2011, 46 (6),2152–2156. doi: 10.1016/j.ejmech.2011.02.069
   PubMed Web of Science ®Google Scholar
• Mamaghani, M.; Larghani, T.H. Ultrasound Promoted One-pot Three-component Synthesis of Novel 7-aryl-8H-benzo[h]indeno[1,2-b]quinolin-8-ones Under Solvent-free Conditions. J. Chem. Res. 2012, 36 (4),235–237. doi: 10.3184/174751912X13319177859559
   Web of Science ®Google Scholar
• Patil, D.R.; Deshmukh, M.B.; Salunkhe, S.M.; Anbhule, P.V. A Simple Synthesis of Trisubstituted Quinolines Through Transesterification. J. Heterocyclic Chem. 2011, 48 (6),1342–1346. doi: 10.1002/jhet.711
   Web of Science ®Google Scholar
• Furniss, B.S.; Hannaford, A.J.; Smith, P.W.G.; Tatchell, A.R. Vogel’s Textbook of Practical Organic Chemistry;5th ed.;Longman Scientific and Technical: Harlow, 1989.
   Google Scholar
• Fehnel, E.A.; Deyrup, J.A.; Davidson, M.B. Quinoline Analogs of Podophyllotoxin. II. Friedländer Reactions with Tetronic Acid: A General Method for the Preparation of 2-Hydroxymethyl-3-quinolinecarboxylic Acid Lactones1. J. Org. Chem. 1958, 23 (12), 1996–2001. doi: 10.1021/jo01106a051
   Web of Science ®Google Scholar
• Schmith, K.; Reymann, F.E. Experimentelle og kliniske undersogelser over gonococcers folsomhed overfor sulfapyridin. Nord. Med. 1940, 8, 2493–2499.
   Google Scholar
• Bouley, R.; Ding, D.; Peng, Z.; Bastian, M.; Lastochkin, E.; Song, W.; Suckow, M.A.; Schroeder, V.A.; Wolter, W.R.; Mobashery, S.; Chang, M. Structure–Activity Relationship for the 4(3H)-Quinazolinone Antibacterials. J. Med. Chem. 2016, 59 (10), 5011–5021. doi: 10.1021/acs.jmedchem.6b00372
   PubMed Web of Science ®Google Scholar