Microwave-assisted synthesis of diverse pyrrolo[3,4- c ]quinoline-1,3- diones and their antibacterial activities

ACS Combinatorial Science

Volumn 16, Issue 7, 2014, Pages 333-341

  Xia, Likai ^a   Idhayadhulla, Akber ^a   Lee, Yong Rok ^a   Kim, Sung Hong ^b   Wee, Young Jung ^a  

^a Yeungnam University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

antibacterial activity; isatins; microwave irradiation; pyrrolo 3,4 c quinoline 1,3 diones; ketoamides

Indexed keywords

ANTIINFECTIVE AGENT; MALEIMIDE DERIVATIVE; QUINOLINE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; GROWTH, DEVELOPMENT AND AGING; MICROBIAL SENSITIVITY TEST; MICROWAVE RADIATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MALEIMIDES; MICROBIAL SENSITIVITY TESTS; MICROWAVES; MOLECULAR STRUCTURE; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84904302509     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co500002s     Document Type: Article

References (79)

1. Russ, T. H.; Pramanik, A.; Khansari, M. E.; Wong, B. M.; Hossain, M. A. A quinoline based bis-urea receptor for anions: A selective receptor for hydrogen sulfate Nat. Prod. Commun. 2012, 7, 301-304
2. Cai, X.-H.; Li, Y.; Su, J.; Liu, Y.-P.; Li, X.-N.; Luo, X.-D. Novel indole and quinoline alkaloids from Melodinus yunnanensis Nat. Prod. Bioprospect. 2011, 1, 25-28
3. Isaac-Marquez, A. P.; McChesney, J. D.; Nanayakara, N. P. D.; Satoskar, A. R.; Lezama-Davila, C. M. Leishmanicidal activity of racemic ±8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3, 4-dichlorophenoxy]quinoline Nat. Prod. Commun. 2010, 5, 387-390
4. Michael, J. P. Quinoline, quinazoline, and acridone alkaloids Nat. Prod. Rep. 2008, 25, 166-187
5. Michael, J. P. Quinoline, quinazoline, and acridone alkaloids Nat. Prod. Rep. 2007, 24, 223-246
6. Michael, J. P. Quinoline, quinazoline and acridone alkaloids Nat. Prod. Rep. 2005, 22, 627-646 (Pubitemid 41457418)
7. Michael, J. P. Quinoline, quinazoline and acridone alkaloids Nat. Prod. Rep. 2004, 21, 650-668 (Pubitemid 39459644)
8. Michael, J. P. Quinoline, quinazoline and acridone alkaloids Nat. Prod. Rep. 2003, 20, 476-493 (Pubitemid 37298577)
9. Michael, J. P. Quinoline, quinazoline and acridone alkaloids Nat. Prod. Rep. 2002, 19, 742-760 (Pubitemid 36029228)
10. Michael, J. P. Quinoline, quinazoline and acridone alkaloids Nat. Prod. Rep. 2001, 18, 543-559 (Pubitemid 33016993)
11. Gorka, A. P.; de Dios, A.; Roepe, P. D. Quinoline drug-heme interactions and implications for antimalarial cytostatic versus cytocidal activities J. Med. Chem. 2013, 56, 5231-5246
12. Michael, J. P. Quinoline, quinazoline, and acridone alkaloids Nat. Prod. Rep. 2008, 25, 166-187
13. Michael, J. P. Quinoline, quinazoline, and acridone alkaloids Nat. Prod. Rep. 2007, 24, 223-246
14. Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines J. Org. Chem. 1999, 64, 3595-3607
15. Atkins, R. J.; Breen, G. F.; Crawford, L. P.; Grinter, T. J.; Harris, M. A.; Hayes, J. F.; Moores, C. J.; Saunders, R. N.; Share, A. C.; Walsgrove, T. C.; Wicks, C. Synthetic Routes to Quinoline Derivatives: Novel Syntheses of 3-Butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-Butyryl-8-(2- hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline Org. Process Res. Dev. 1997, 1, 185-197
16. Lilienkampf, A.; Mao, J.; Wan, B.; Wang, Y.; Franzblau, S. G.; Kozikowski, A. P. Structure-Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating Mycobacterium tuberculosis J. Med. Chem. 2009, 52, 2109-2118
17. Nasveld, P.; Kitchener, S. Treatment of Acute Vivax Malaria with Tafenoquine Trans. R. Soc. Trop. Med. Hyg. 2005, 99, 2-5 (Pubitemid 39517029)
18. Leatham, P. A.; Bird, H. A.; Wright, V.; Seymour, D.; Gordon, A. A double blind study of antrafenine, naproxen and placebo in osteoarthrosis Eur. J. Rheumatol. Inflamm. 1983, 6, 209-211 (Pubitemid 14191446)
19. Insuasty, B.; Montoya, A.; Becerra, D.; Quiroga, J.; Abonia, R.; Robledo, S.; Vélez, I. D.; Upegui, Y.; Nogueras, M.; Cobo, J. Synthesis of novel analogs of 2-pyrazoline obtained from [(7-chloroquinolin-4-yl)amino]chalcones and hydrazine as potential antitumor and antimalarial agents Eur. J. Med. Chem. 2013, 67, 252-262
20. Sun, J.; Zhu, H.; Yang, Z.-M.; Zhu, H.-L. Synthesis, molecular modeling and biological evaluation of 2-aminomethyl-5-(quinolin-2-yl)-1,3,4-oxadiazole- 2(3 H)-thione quinolone derivatives as novel anticancer agent Eur. J. Med. Chem. 2013, 60, 23-28
21. Mahamoud, A.; Chevalier, J.; Davin-Regli, A.; Barbe, J.; Pages, J.-M. Quinoline derivatives as promising inhibitors of antibiotic efflux pump in multidrug resistant Enterobacter aerogenes isolates Curr. Drug Targets 2006, 7, 843-847
22. Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J. T. Synthesis, anticonvulsant and antihypertensive activities of 8-substituted quinoline derivatives Biol. Pharm. Bull. 2004, 27, 1683-1687 (Pubitemid 41701664)
23. Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. A new series of PDGF receptor tyrosine kinase inhibitors: 3-Substituted quinoline derivatives J. Med. Chem. 1994, 37, 2129-2137 (Pubitemid 24228439)
24. Wilson, W. D.; Zhao, M.; Patterson, S. E.; Wydra, R. L.; Janda, L.; Strekowski, L.; Schinazi, R. F. Design of RNA interactive anti-HIV-1 agents: Unfused aromatic intercalators Med. Chem. Res. 1992, 2, 102-110
25. Strekowski, L.; Mokrosz, J. L.; Honkan, V. A.; Czarny, A.; Cegla, M. T.; Wydra, R. L.; Patterson, S. E.; Schinazi, R. F. Synthesis and quantitative structure-activity relationship analysis of 2-(aryl or heteroaryl)quinolin-4- amines, A new class of anti-HIV-1 agents J. Med. Chem. 1991, 34, 1739-1746
26. Kunin, C. M.; Ellis, W. Y. Antimicrobial activities of mefloquine and a series of related compounds Antimicrob. Agents Chemother. 2000, 44, 848-852 (Pubitemid 30165259)
27. Jayaprakash, S.; Iso, Y.; Wan, B.; Franzblau, S. G.; Kozikowski, A. P. Design, synthesis, and SAR studies of mefloquine-based ligands as potential antituberculosis agents ChemMedChem. 2006, 1, 593-597 (Pubitemid 44105784)
28. Mao, J.; Yuan, H.; Wang, Y.; Wan, B.; Pieroni, M.; Huang, Q.; Van Breemen, R. B.; Kozikowski, A. P.; Franzblau, S. G. From serendipity to rational antituberculosis drug discovery of mefloquine-isoxazole carboxylic acid esters J. Med. Chem. 2009, 52, 6966-6978
29. Murai, Z.; Baran, B.; Tolna, J.; Szily, E.; Gazdag, G. Neuropsychiatric symptoms caused by mefloquine (report of several cases) Orv. Hetil. 2005, 146, 133-136 (Pubitemid 46118673)
30. Bermudez, L. E.; Kolonoski, P.; Seitz, L. E.; Petrofsky, M.; Reynolds, R.; Wu, M.; Young, L. S. SRI-286, A thiosemicarbazole, in combination with mefloquine and moxifloxacin for treatment of murine Mycobacterium avium complex disease Antimicrob. Agents Chemother. 2004, 48, 3556-3558 (Pubitemid 39129359)
31. Thomas, K. D.; Adhikari, A. V.; Shetty, N. S. Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1,2,3-triazole moiety Eur. J. Med. Chem. 2010, 45, 3803-3810
32. Kato, Y.; Nagao, Y. Effect of polyvinylpyrrolidone on sperm function and early embryonic development following intracytoplasmic sperm injection in human assisted reproduction Reprod. Med. Biol. 2012, 11, 165-176
33. Jouyban, A.; Fakhree, M. A. A.; Shayanfar, A. Review of pharmaceutical applications of N -methyl-2-pyrrolidone J. Pharm. Pharm. Sci. 2010, 13, 524-535
34. Gibbison, R. Diverse applications of N -alkyl pyrrolidones Spec. Chem. Mag. 2002, 22, 15-16
35. Shorvon, S. Pyrrolidone derivatives Lancet 2001, 358, 1885-1892 (Pubitemid 34008660)
36. Decker, M.; Arneric, S. P. In Neuronal Nicotinic Receptors: Pharmacology and Therapeutic Opportunities; Arneric, S. P.; Brioni, J. D., Eds.; Wiley-Liss: New York, 1999; pp 395-411.
37. Holladay, M. W.; Dart, M. J.; Lynch, J. K. Neuronal nicotinic acetylcholine receptors as targets for drug discovery J. Med. Chem. 1997, 40, 4169-4194 (Pubitemid 28042300)
38. Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach, 3 rd ed.; John Wiley & Sons: Chichester, U.K., 2009; Chapter 6 and references therein.
39. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Amsterdam, 1990; pp 1-161.
40. Ikai, T.; Azam, A. K. M. F.; Kuzuba, M.; Kuwabara, T.; Maeda, K.; Takahashi, K.; Kanoh, S. Synthesis of seleno[3,4- c ]pyrrole-4,6-dione-based polymers for polymer solar cells Synth. Met. 2012, 162, 1707-1712
41. Wu, Z.-L.; Li, A.-Y.; Fan, B.-H.; Xue, F.; Adachi, C.; Ouyang, J.-Y. Phenanthrene-functionalized 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4- c ]pyrrole-1,4-diones as donor molecules for solution-processed organic photovoltaic cells Sol. Energy Mater. Sol. Cells 2011, 95, 2516-2523
42. Zou, Y.; Najari, A.; Berrouard, P.; Beaupré, S.; Aïch, B. R.; Tao, Y.; Leclerc, M. A thieno[3,4- c ]pyrrole-4,6-dione-based copolymer for efficient solar cells J. Am. Chem. Soc. 2010, 132, 5330-5331
43. Piliego, C.; Holcombe, T. W.; Douglas, J. D.; Woo, C. H.; Beaujuge, P. M.; Fréchet, J. M. J. Synthetic control of structural order in N -alkylthieno[3,4- c ]pyrrole-4,6-dione-based polymers for efficient solar cells J. Am. Chem. Soc. 2010, 132, 7595-7597
44. Mahboobi, S.; Eichhorn, E.; Popp, A.; Sellmer, A.; Elz, S.; Möllmann, U. 3-Bromo-4-(1 H -3-indolyl)-2,5-dihydro-1 H -2,5-pyrroledione derivatives as new lead compounds for antibacterially active substances Eur. J. Med. Chem. 2006, 41, 176-191
45. Sancelme, M.; Fabre, S.; Prudhomme, M. Antimicrobial activities of indolocarbazole and bis-indole protein kinase C inhibitors J. Antibiot. 1994, 47, 792-798 (Pubitemid 24233410)
46. Slater, M. J.; Cockerill, G. S.; Robinson, J. E. Preparation of antiviral heterocyclylindole derivatives. Int. Patent WO9507910A1, 1995.
47. Kim, Y.-S.; Sagara, J.; Kawai, A. Studies on the antiviral activity of protein kinase inhibitors against the replication of vesicular stomatitis virus Biol. Pharm. Bull. 1995, 18, 895-899
48. Slater, M. J.; Cockerill, G. S.; Littler, E.; Yeates, C. L. Indole derivatives with antiviral activity. Int. Patent WO9318766A1, 1993.
49. Slater, M. J.; Cockerill, G. S.; Littler, E. Antiviral bis(indolyl)pyrrolidones. Int. Patent WO9318765A1, 1993.
50. Davis, P. D.; Hill, C. H.; Lawton, G.; Nixon, J. S.; Wilkinson, S. E.; Hurst, S. A.; Keech, E.; Turner, S. E. Inhibitors of protein kinase C. 1. 2,3-Bisarylmaleimides J. Med. Chem. 1992, 35, 177-184
51. Mahboobi, S.; Eichhorn, E.; Winkler, M.; Sellmer, A.; Möllmann, U. Antibacterial activity of a novel series of 3-bromo-4-(1 H -3-indolyl)-2,5- dihydro-1 H -2,5-pyrroledione derivatives: An extended structure-activity relationship study Eur. J. Med. Chem. 2008, 43, 633-656 (Pubitemid 351323998)
52. Sharma, S.; Ravichandran, V.; Jain, P. K.; Mourya, V. K.; Agrawal, R. K. Prediction of caspase-3 inhibitory activity of 1,3-dioxo-4-methyl-2,3-dihydro-1 H -pyrrolo[3,4- c ] quinolines: QSAR study J. Enzyme Inhib. Med. Chem. 2008, 23, 424-431 (Pubitemid 351935066)
53. Okun, I.; Malarchuk, S.; Dubrovskaya, E.; Khvat, A.; Tkachenko, S.; Kysil, V.; Kravchenko, D.; Ivachtchenko, A. Screening for caspase-3 inhibitors: Effect of a reducing agent on identified hit chemotypes J. Biomol. Screening 2006, 11, 694-703 (Pubitemid 44315967)
54. Kravchenko, D. V.; Kysil, V. M.; Tkachenko, S. E.; Maliarchouk, S.; Okun, I. M.; Ivachtchenko, A. V. Pyrrolo[3,4- c ]quinoline-1,3-diones as potent caspase-3 inhibitors. Synthesis and SAR of 2-substituted 4-methyl-8-(morpholine- 4-sulfonyl)-pyrrolo[3,4- c ]quinoline-1,3-diones Eur. J. Med. Chem. 2005, 40, 1377-1383 (Pubitemid 41618281)
55. Summa, V.; Pace, P.; Di, F. M. E.; Martin, H. J. I.; Nizi, E. Preparation of imidazole derivatives as inhibitors of hepatitis C virus polymerases. U.K. Patent GB2450771A, 2009.
56. Thomas, J. W.; Tallman, J. F. Characterization of photoaffinity labeling of benzodiazepine binding sites J. Biol. Chem. 1981, 256, 9838-9842 (Pubitemid 12176184)
57. Thale, Z.; Johnson, T.; Tenney, K.; Wenzel, P. J.; Lobkovsky, E.; Clardy, J.; Media, J.; Pietraszkiewicz, H.; Valeriote, F. A.; Crews, P. Structures and cytotoxic properties of sponge-derived bisannulated acridines J. Org. Chem. 2002, 67, 9384-9391 (Pubitemid 36033921)
58. Makki, M. S. T.; Bakhotmah, D. A.; Abdel-Rahman, R. M. Highly efficient synthesis of novel fluorine bearing quinoline-4-carboxylic acid and the related compounds as amylolytic agents. Int J. Org. Chem. 2012, 2, 49-55
59. Kravchenko, D. V.; Kysil, V. M.; Tkachenko, S. E.; Maliarchouk, S.; Okun, I. M.; Ivachtchenko, A. V. New variant of the Pfitzinger reaction. Synthesis and chemical transformations of substituted 2-aminomethyl-quinoline-3,4- dicarboxylic acids Heterocycl. Commun. 2006, 12, 15-18 (Pubitemid 43624967)
60. Kravchenko, D. V.; Kysil, V. M.; Tkachenko, S. E.; Maliarchouk, S.; Okun, I. M.; Ivachtchenko, A. V. Synthesis and caspase-3 inhibitory activity of 8-sulfonyl-1,3-dioxo-2,3-dihydro-1 H -pyrrolo[3,4- c ]quinolines Farmaco 2005, 60, 804-809 (Pubitemid 41483038)
61. Mortoni, A.; Martinelli, M.; Piarulli, U.; Regalia, N.; Gagliardi, S. Microwave-assisted solvent-free synthesis of a quinoline-3,4-dicarboximide library on inorganic solid supports Tetrahedron Lett. 2004, 45, 6623-6627 (Pubitemid 39106819)
62. Ivachtchenko, A. V.; Kobak, V. V.; Ilyin, A. P.; Trifilenkov, A. S.; Busel, A. A. New scaffolds for combinatorial synthesis. II. 6- Sulfamoylquinolinecarboxylic acids J. Comb. Chem. 2003, 5, 645-652 (Pubitemid 37206170)
63. Li, J.; Su, S.; Huang, M.; Song, B.; Li, C.; Jia, X. Unexpected isocyanide-based cascade cycloaddition reaction with methyleneindolinone Chem. Commun. 2013, 49, 10694-10696
64. Xia, L.; Lee, Y. R. Efficient one-step synthesis of pyrrolo[3,4- c ]quinoline-1,3-dione derivatives by organocatalytic cascade reactions of isatins and β-ketoamides Org. Biomol. Chem. 2013, 11, 5254-5263
65. Irfan, M.; Glasnov, T. N.; Kappe, C. O. Heterogeneous catalytic hydrogenation reactions in continuous-flow reactors ChemSusChem 2011, 4, 300-316
66. Kappe, C. O.; Van der Eycken, E. Click chemistry under non-classical reaction conditions Chem. Soc. Rev. 2010, 39, 1280-1290
67. Kappe, C. O. Microwave dielectric heating in synthetic organic chemistry Chem. Soc. Rev. 2008, 37, 1127-1139
68. Wathey, B.; Tierney, J.; Lidstrom, P.; Westman, J. The impact of microwave-assisted organic chemistry on drug discovery Drug Discovery Today 2002, 7, 373-380 (Pubitemid 34228904)
69. Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. Increasing rates of reaction: microwave-assisted organic synthesis for combinatorial chemistry J. Comb. Chem. 2002, 4, 95-105
70. Larhed, M.; Moberg, C.; Hallberg, A. Microwave-accelerated homogeneous catalysis in organic chemistry Acc. Chem. Res. 2002, 35, 717-727
71. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis: A review Tetrahedron 2001, 57, 9225-9283 (Pubitemid 33016768)
72. Wasserscheid, P.; Welton, T.; Eds. Ionic Liquids in Synthesis, 2 nd ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008.
73. Kappe, C. O.; Stadler, A., Eds. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, Germany, 2005.
74. Olofsson, K.; Hallberg, A.; Larhed, M. Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
75. Xia, L.; Lee, Y. R. Efficient one-pot synthesis of multi-substituted dihydrofurans by ruthenium(II)-catalyzed [3 + 2] cycloaddition of cyclic or acyclic diazodicarbonyl compounds with olefins Adv. Synth. Catal. 2013, 355, 2361-2374
76. Bauer, A. W.; Kirby, W. M.; Sherris, J. C.; Turck, M. Antibiotic susceptibility testing by a standardized single disk method Am. J. Clin. Pathol. 1966, 45, 493-496
77. Idhayadhulla, A.; Xia, L.; Lee, Y. R.; Kim, S. H.; Wee, Y.-J.; Lee, C.-S. Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities Bioorg. Chem. 2013, 52, 77-82
78. Kidwai, M.; Bhushan, K. R.; Sapra, P.; Saxena, R. K.; Gupta, R. Alumina-supported synthesis of antibacterial quinolines using microwaves Bioorg. Med. Chem. 2000, 8, 69-72 (Pubitemid 30125656)
79. Sharma, P.; Rane, N.; Gurram, V. K. Synthesis and QSAR studies of pyrimido[4,5- d ]pyrimidine-2,5-dione derivatives as potential antimicrobial agents Bioorg. Med. Chem. Lett. 2004, 14, 4185-4190