Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 4, 2012, Pages 1643-1648

  Paul, Nidhin ^a   Murugavel, Muthuchamy ^a   Muthusubramanian, Shanmugam ^a   Sriram, Dharmarajan ^b  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

Antimycobacterial activity; Double Friedlander annulation; Bisquinoline( ) Camphor 10 sulfonic acid (CSA); Mycobacterium tuberculosis

Indexed keywords

2 (3 BROMOPHENYL) 6 CHLORO 3 [4 (6 CHLORO 4 PHENYL 2 QUINOLYL)PHENOXY] 4 PHENYLQUINOLINE; 2 (4 BROMOPHENYL) 6 CHLORO 3 [4 (6 CHLORO 4 PHENYL 2 QUINOLYL)PHENOXY] 4 PHENYLQUINOLINE; 2,8 BIS[(TRIFLUOROMETHYL) 4 AMINO QUINOLINE]; 4 (3,4 DIMETHOXYPHENYL) 6,7 DIMETHOXY 2 (1,2,4 TRIAZOL 1 YLMETHYL) 3 QUINOLINECARBOXYLIC ACID ETHYL ESTER; BEDAQUILINE; CAMPHORSULFONIC ACID; IRINOTECAN; MEFLOQUINE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; SULFONIC ACID DERIVATIVE; TALNETANT; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANALYSIS; ANIMAL CELL; ANIMAL CELL CULTURE; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CARBON NUCLEAR MAGNETIC RESONANCE; DOUBLE FRIEDLANDER ANNULATION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; FIBROBLAST; HETERONUCLEAR MULTIPLE BOND CORRELATION; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TUBERCULOSIS;

DRYOBALANOPS; MYCOBACTERIUM TUBERCULOSIS;

EID: 84856641119     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.119     Document Type: Article

References (86)

1. (a) Duncan, K. Chem. Ind. 1997, 861
2. (b) Daffe, M.; Draper, P. Adv. Microb. Physiol. 1998, 39, 131.
3. Cole, S. T.; Alzari, P. M. Biochem. Soc. Trans. 2007, 35, 1321.
4. Young, D. B.; Perkins, M. D.; Duncan, K.; Barry, C. E. Clin. Invest. 2008, 118, 1255.
5. (a) De cock, K. M.; Chaission, R. E. Int. J. Tuberc. Lung Dis. 1999, 3, 457
6. (b) Upadhayaya, R. S.; Kulkarni, G. M.; Vasireddy, N. R.; Vandavasi, J. K.; Dixit, S. S.; Sharma, V.; Chattopadhyaya, J. Bioorg. Med. Chem. 2009, 17, 4681.
7. (a) Nivin, B.; Nicolas, P.; Gayer, M.; Frieden, T. R.; Fujiwara, P. I. Clin. Infect. Dis. 1998, 26, 303
8. (b) Weltman, A. C.; Rose, D. N. Arch. Intern. Med. 1994, 154, 2161
9. (c) Pablos-Mendez, A.; Raviglione, M. C.; Laszlo, A.; Binkin, N.; Rieder, H. L.; Bustreo, F.; Cohn, D. L.; Lambregts-van Weezenbeck, C. S. B.; Kim, S. J.; Chaulet, P.; Nunn, P. N. Eng. J. Med. 1998, 338, 1641
10. (d) Sivakumar, P. M.; Babu, S. K. G.; Mukesh, D. Chem. Pharm. Bull. 2007, 55, 44;
11. (e) Brown, A. K.; Papaemmanouil, A.; Bhowruth, V.; Bhatt, A.; Dover, L. G.; Besra, G. S. Microbiology 2007, 153, 3314
12. (f) Mao, J.; Eoh, H.; He, R.; Wang, Y.; Wan, B. G.; Franzblau, S. G.; Crick, D. C.; Kozikowski, A. P. Bioorg. Med. Chem. Lett. 2008, 18, 5320.
13. Bass, J. B.; Farer, L. S.; Hopewell, P. C.; O'Brien, R.; Jacobs, R. F.; Ruben, F.; Snider, D. E.; Thornton, G. Am. J. Respir. Crit. Care Med. 1994, 149, 1359.
14. Davies, P. D. O.; Yew, W. W. Expert Opin. Investig. Drugs 2003, 12, 1297.
15. Larsen, R. D.; Corley, E. G.; King, A. O.; Carroll, J. D.; Davis, P.; Verhoeven, T. R.; Reider, P. J.; Labelle, M.; Gauthier, J. Y.; Xiang, Y. B.; Zamboni, R. J. J. Org. Chem. 1996, 61, 3398.
16. (a) Chen, Y. L.; Fang, K. C.; Sheu, J. Y.; Hsu, S. L.; Tzeng, C. C. J. Med. Chem. 2001, 44, 2374
17. (b) Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, M. Eur. J. Med. Chem. 2000, 35, 1021.
18. (a) Kouznetsov, V. V.; Vargas Mendez, L. Y.; Melendez Gomez, C. M. Curr. Org. Chem. 2005, 9, 141
19. (b) Eswaran, S.; Adhikari, A. V.; Chowdhury, I. H.; Pal, N. K.; Thomas, K. D. Eur. J. Med. Chem. 2010, 45, 3374
20. (c) Zora, M.; Velioglu, O. J. Organomet. Chem. 2008, 693, 2159
21. (d) Eswaran, S.; Adhikari, A. V.; Shetty, N. S. Eur. J. Med. Chem. 2009, 44, 4637
22. (e) David, E.; Pellet-Rostaing, S.; Lemaire, M. Tetrahedron 2007, 63, 8999
23. (f) Chen, Y. L.; Zhao, Y. L.; Lu, C. M.; Tzeng, C. C.; Wang, J. P. Bioorg. Med. Chem. 2006, 14, 4373.
24. Wiesner, J.; Ortmann, R.; Jomaa, H.; Schlitzer, M. Angew. Chem., Int. Ed. 2003, 42, 5274.
25. Elliott, J. M.; Carling, R. W.; Chambers, M.; Chicchi, G. G.; Hutson, P. H.; Jones, A. B.; MacLeod, A.; Marwood, R.; Meneses-Lorente, G.; Mezzogori, E.; Murray, F.; Rigby, M.; Royo, I.; Russell, M. G. N.; Sohal, B.; Tsao, K. L.; Williams, B. Bioorg. Med. Chem. Lett. 2006, 16, 5748.
26. Fuchs, C.; Mitchell, E. P.; Hoff, P. M. Cancer Treat. Rev. 2006, 32, 491.
27. (a) Mizuno, M.; Inagaki, A.; Yamashita, M.; Soma, N.; Maeda, Y.; Nakatani, H. Tetrahedron 2006, 62, 4065
28. (b) Mizuno, M.; Yamashita, M.; Sawai, Y.; Nakamoto, K.; Goto, M. Tetrahedron 2006, 62, 8707.
29. Mikata, Y.; Yokoyama, M.; Ogura, S.-I.; Okura, I.; Kawasaki, M.; Maeda, M.; Yano, S. Bioorg. Med. Chem. Lett. 1998, 8, 1243.
30. Praveen, C.; DheenKumar, P.; Muralidharan, D.; Perumal, P. T. Bioorg. Med. Chem. Lett. 2010, 20, 7292.
31. Lombard, M. C.; N'Da, D. D.; Breytenbach, J. C.; Smith, P. J.; Lategan, C. A. Bioorg. Med. Chem. Lett. 2010, 20, 6975.
32. Chen, S.; Chen, R.; He, M.; Pang, R.; Tan, Z.; Yang, M. Bioorg. Med. Chem. 2009, 17, 1948.
33. Woodrow, M. D.; Ballantine, S. P.; Barker, M. D.; Clarke, B. J.; Dawson, J.; Dean, T. W.; Delves, C. J.; Evans, B.; Gough, S. L.; Guntrip, S. B.; Holman, S.; Holmes, D. S.; Kranz, M.; Lindvaal, M. K.; Lucas, F. S.; Neu, M.; Ranshaw, L. E.; Solanke, Y. E.; Somers, D. O.; Ward, P.; Wiseman, J. O. Bioorg. Med. Chem. Lett. 2009, 19, 5261.
34. (a) Raynes, K. Int. J. Parasitol. 1999, 29, 67
35. (b) Guillon, J.; Moreau, S.; Mouray, E.; Sinou, V.; Forfar, I.; Fabre, S. B.; Desplat, V.; Millet, P.; Parzy, D.; Jarry, C.; Grellier, P. Bioorg. Med. Chem. 2008, 16, 9133.
36. Jachak, S. M.; Saklani, A. Curr. Sci. 2007, 92, 1251.
37. Vennerstrom, J. L.; Ellis, W. Y.; Ager, A. L.; Anderaen, S. L.; Gerena, L.; Milhous, W. K. J. Med. Chem. 1992, 35, 2129.
38. Alfredson, T. V.; Maki, A. H.; Waring, M. J. Biochem. 1991, 30, 9665.
39. Raynes, K.; Galatis, D.; Cowman, A. F.; Tilley, L.; Deady, L. W. J. Med. Chem. 1995, 38, 204.
40. Palit, P.; Paira, P.; Hazra, A.; Banerjee, S.; Gupta, A. D.; Dastidar, S. G.; Mondal, N. B. Eur. J. Med. Chem. 2009, 44, 845.
41. Larghi, E. L.; Bohn, M. L.; Kaufman, T. S. Tetrahedron 2009, 65, 4257.
42. Kaur, K.; Jain, M.; Khan, S. I.; Jacob, M. R.; Tekwani, B. L.; Singh, S.; Pal Singh, P.; Jaina, R. Bioorg. Med. Chem. 2011, 19, 197.
43. Tewari, S.; Chauhan, P. M. S.; Bhaduri, A. P.; Fatima, N.; Chatterjee, R. K. Bioorg. Med. Chem. Lett. 2000, 10, 1409.
44. Strekowski, L.; Say, M.; Zegrocka, O.; Tanious, F. A.; David Wilson, W.; Manzel, L.; Macfarlane, D. E. Bioorg. Med. Chem. 2003, 11, 1079.
45. (a) Murugesan, D.; Palaniappan, S.; Perumal, Y.; Arnab, C.; Valakunja, N.; Sriram, D. Bioorg. Med. Chem. 2008, 16, 3408
46. (b) Annamaria, L.; Jialin, M.; Baojie, W.; Yuehong, W.; Scott, G. F.; Alan, P. K. J. Med. Chem. 2009, 52, 2109
47. (c) Sarva, J.; Yasuyoshi, I.; Baojie, W.; Scott, G. F.; Alan, P. K. Chem. Med. Chem. 2006, 1, 593
48. (d) Amit, N.; Vikramdeep, M.; Alpeshkumar, M.; Rahul, E. J. Bioorg. Med. Chem. 2007, 15, 626
49. (e) Dinakaran, M.; Senthilkumar, P.; Yogeeswari, P.; China, A.; Nagaraja, V.; Dharmarajan, S. Int. J. Antimicrob. Agents 2008, 31, 337
50. (f) Jain, R.; Vaitilingam, B.; Nayyar, A.; Palde, P. B. Bioorg. Med. Chem. Lett. 2003, 13, 1051.
51. Rustomjee, R.; Diacon, A. H.; Allen, J.; Venter, A.; Reddy, C.; Patientia, R. F.; Mthiyane, T. C. P.; De Marez, T.; Van Heeswijk, R.; Kerstens, R.; Koul, A.; De Beule, K.; Donald, P. R.; McNeeley, A. F. Antimicrob. Agents Chemother. 2008, 52, 2831.
52. Mital, A.; Singh Negi, V.; Ramachandran, U. ARKIVOC 2006, 10, 220.
53. (a) Manikannan, R.; Muthusubramanian, S.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2010, 20, 3352
54. (b) Manikannan, R.; Venkatesan, R.; Muthusubramanian, S.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2010, 20, 6920
55. (c) Ponpandian, T.; Muthusubramanian, S. Tetrahedron Lett. 2011, 52, 1520
56. (d) Saravanan, S.; Azath, I. A.; Muthusubramanian, S. J. Org. Chem. 2008, 73, 2323;
57. (e) Paul, N.; Muthusubramanian, S. Tetrahedron Lett. 2011, 52, 3743
58. (f) Ravindran, G.; Paul, N.; Muthusubramanian, S.; Perumal, S. J. Sulfur Chem. 2008, 29, 575
59. (g) Nagaraj, M.; Boominathan, M.; Muthusubramanian, S.; Bhuvanesh, N. Org. Biomol. Chem. 2011, 9, 4642
60. (h) Boominathan, M.; Nagaraj, M.; Muthusubramanian, S.; Krishnakumar, R. V. Tetrahedron 2011, 67, 6057
61. (i) Paul, N.; Muthusubramanian, S.; Bhuvanesh, N. New J. Chem. 2011, 35, 2607
62. Paul, N.; Kaladevi, S.; Muthusubramanian, S. Helv. Chim. Acta 2011. doi:10.1002/hlca.201100263
63. Chitra, S.; Paul, N.; Muthusubramanian, S.; Manisankar, P.; Yogeeswari, P.; Sriram, D. Eur. J. Med. Chem. 2011, 46, 4897
64. Chitra, S.; Paul, N.; Muthusubramanian, S.; Manisankar, P.; Yogeeswari, P.; Sriram, D. Eur. J. Med. Chem. 2011, 46, 5465
65. Chitra, S.; Paul, N.; Muthusubramanian, S.; Manisankar, P. Green Chem. 2011, 13, 2777.
66. (a) Wu, Y.-S.; Cai, J.; Hu, Z.-Y.; Lin, G. H. Tetrahedron Lett. 2004, 45, 8949
67. (b) Cheng, H.-G.; Chen, C. B.; Tan, F.; Chang, N.-J.; Chen, J.-R.; Xiao, W.-J. Eur. J. Org. Chem. 2010, 4976
68. (c) Kazuhiro, K.; Yuu, S.; Hisatoshi, K. J. Heterocycles 2009, 78, 2033
69. (d) Kazuhiro, K.; Yuta, O.; Hisatoshi, K. Synthesis 2009, 9, 1494.
70. N. Paul et al. / Bioorg. Med. Chem. Lett. 22 (2012) 1643-1648 1647
71. (a) Reynolds, R. C.; Bansal, N.; Rose, J.; Friedrich, J.; Suling, W. J.; Maddry, J. A. Carbohydr. Res. 1999, 317, 164
72. (b) Lees, A. W.; Tyrrell, W. F.; Smith, J.; Allan, G. W. Br. J. Dis. Chest 1970, 64, 85;
73. (c) Kahana, L. M. Biomed. Pharmacother. 1990, 44, 21
74. (d) Marshall Clarke, G. B.; Cuthbert, J.; Cuthbert, R. J.; Lees, A. W. Br. J. Dis. Chest 1972, 66, 272
75. (e) Dickinson, J. M.; Ellard, G. A.; Mitchison, D. A. Tubercle 1968, 49, 351
76. (f) Yendapally, R.; Lee, R. E. Bioorg. Med. Chem. Lett. 2008, 18, 1607
77. (g) Tuberculosis 2008, 88, 102.
78. (h) Dover, L. G.; Coxon, G. D. J. Med. Chem. 2011, 54, 6157
79. (a) Uttley, A. H. C.; Collins, C. H. Tubercle 1988, 69, 193
80. (b) Chadwick, M.; Nicholson, G.; Gaya, H. Am. J. Med. 1989, 87, S35
81. (c) Sriram, D.; Yogeeswari, P.; Basha, J. S.; Radha, D. R.; Nagaraja, V. Bioorg. Med. Chem 2005, 13, 5774
82. (d) Jonchevska, M.; Talevski, S.; Bakalova, E.; Kungulovska, O. Tuber. Lung Dis. 1995, 76, 85
83. (e) Cobanlt, B.; Zamani, A. Tuber. Lung Dis. 1994, 75, 13
84. (f) Donald, P. R.; Diacon, A. H. Tuberculosis 2008, 88, S75.
85. (a) Mosmann, T. J. Immunol. Methods 1983, 65, 55
86. (b) Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Campbell, H.; Mayo, J.; Boyd, M. J. Natl. Cancer Inst. 1991, 83, 757.