Mechanism and synthesis of pharmacologically active quinolones from Morita-Baylis-Hillman adducts

Tetrahedron

Volumn 66, Issue 24, 2010, Pages 4370-4376

  Amarante, Giovanni W ^a   Benassi, Mario ^a   Pascoal, Robert N ^a   Eberlin, Marcos N ^a   Coelho, Fernando ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

4 Quinolones; Alzheimer disease; Antibiotics; Morita Baylis Hillman; N Oxides

Indexed keywords

1 ( 4 METHOXYBENZYL) 4 OXO 1,4 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 1 ETHYL 6 FLUORO 4 OXO 7 (PIPERAZIN 1 YL) 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; BENZYL QUINOLONE CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; MUSCARINIC M1 RECEPTOR; NORFLOXACIN; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ALLOSTERISM; ALZHEIMER DISEASE; ANTIBACTERIAL ACTIVITY; ARTICLE; CYCLIZATION; CYCLOADDITION; DRUG POTENCY; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; MORITA BAYLIS HILLMAN CYCLOADDITION; PAIN; PRIORITY JOURNAL; SLEEP DISORDER; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 77953123744     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.018     Document Type: Article

References (106)

1. Lescher G.Y., Froelich E.D., Gruet M.D., Bailey J.H., and Brundage R.P. J. Med. Pharm. Chem. 5 (1962) 1063-1065
2. Emmerson A.M., and Jones A.M. J. Antimicrob. Chemother. 51 (2003) 13-20 and references cited therein
3. Wise R. J. Antimicrob. Chemother. 13 (1984) 59-64
4. Naber K.G. Chemotherapy 42 (1996) 1-9
5. Balfour J.A., Todd P.A., and Peters D.H. Drugs 49 (1995) 794-850
6. Jones R.N., and Pfaller M.A. Clin. Infect. Dis. 31 (2000) 16-23
7. Blondeau J.M. J. Antimicrob. Chemother. 43 (1999) 1-11
8. Crumplin G.C., and Smith J.T. Nature 260 (1976) 643-645
9. Gellert M., Mizuuchi K., ÓDea M.H., and Nash H.A. Proc. Natl. Acad. Sci. U.S.A. 73 (1976) 3872-3876
10. Wang J.C. Annu. Rev. Biochem. 54 (1985) 665-697
11. Gootz T.D., and Brighty K.E. Med. Res. Rev. 16 (1996) 433-486
12. Drlica K., and Zhao X. Microbiol. Mol. Biology Rev. 61 (1997) 377-392
13. Zhang S.-X., Feng J., Kuo S.-C., Brossi A., Hamel E., Tropsha A., and Lee K.-H. J. Med. Chem. 43 (2000) 167-176
14. Kuo S.-C., Lee H.-Z., Juang J., Lin Y.-T., Wu T.-S., Chang J.-J., Lednicer D., Paull K.D., Lin C.M., Hamel E., and Lee K.-H. J. Med. Chem. 36 (1993) 1146-1156
15. Melikian, A.; Wright, J.J.; Krasinski, A.; Hu, C.; Novack, A.; Kezer, W.B. WO Patent 2007/059108, May, 24, 2007;
16. Chem. Abstr. 147 (2007) 9883
17. Muller A., Homey B., Soto H., Ge N., Catron D., Buchanan M.E., McClanahan T., Murphy E., Yuan W., Wagner S.N., Barrera J.L., Mohar A., Verastegui E., and Zlotnik A. Nature 410 (2001) 5-56
18. Geula C. Neurobiology 51 (1998) 518-529
19. Ma L., Seager M.A., Wittmann M., Jacobson M., Bickel D., Burno M., Jones K., Graufeld V.K., Xu G., Pearson M., McCampbell A., Gaspar R., Shughrue P., Danziger A., Regan C., Flick R., Pascarella D., Garson S., Doran S., Kreatsoulas C., Veng L., Lindsley C.W., Shipe W., Kuduk S., Sur C., Kinney G., Seabrook G.R., and Ray W.J. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 15950-15955
20. Shipe, W.D.; Lindsley, C.; Hallett, D. WO Patent 2007/100366, September 7, 2007;
21. Chem. Abstr. 147 (2007) 343962
22. Shipe, W.D.; Lindsley, C.; Hallett, D. WO Patent 2007/067489, June 14, 2007;
23. Chem. Abstr. 147 (2007) 72652
24. For a comprehensive review concerning the chemistry of quinolones, see:. Boteva A.A., and Krasnykh O.P. Chem. Heterocycl. Compd. 45 (2009) 757-785
25. For some examples concerning the synthesis of Norfloxacin, see:
26. Zhu S., Wu Y., Yu Z., Shen X., Xu C., Yao J., Huang H., and Jin S. Lett. Org. Chem. 5 (2008) 1-2
27. Bambeke V.F., Michot J.-M., van Eldere J., and Tulkens P.M. Clin. Microbiol. Infect. 11 (2005) 256-280
28. Mitscher L.A. Chem. Rev. 105 (2005) 559-592
29. Kalkote U.R., Sathe V.T., Kharul R.K., Chavan S.P., and Ravindranathan T. Tetrahedron Lett. 37 (1996) 6785-6786
30. Pappalardo M., Omodei-Sale A., and Zanuso G. Farmaco 43 (1988) 489-499
31. Chu D.T.W. J. Heterocycl. Chem. 22 (1985) 1033-1034
32. Koga H., Itoh K., Murayama S., Suzu S., and Irikura T. J. Med. Chem. 23 (1980) 1358-1363
33. For some recent review concerning different aspects of the Morita-Baylis-Hillman reaction, see:
34. Basavaiah D., Rao K.V., and Reddy R.J. Chem. Soc. Rev. 36 (2007) 1581-1588
35. Singh V., and Batra S. Tetrahedron 64 (2008) 4511-4574
36. Almeida W.P., and Coelho F. Quim. Nova 23 (2001) 98-101
37. For new insights about the mechanism of this reaction, see:
38. Santos L.S., Pavam C.H., Almeida W.P., Coelho F., and Eberlin M.N. Angew. Chem., Int. Ed. 43 (2004) 4330-4333
39. Santos L.S., da Silveira Neto B.A., Consorti C.S., Pavam C.H., Almeida W.P., Coelho F., Dupont J., and Eberlin M.N. J. Phys. Org. Chem. 19 (2006) 731-736
40. Aggarwal V.K., Fulford S.Y., and Lloyd-Jones G.C. Angew. Chem., Int. Ed. 44 (2005) 1706-1708
41. Robiette R., Aggarwal V.K., and Harvey J.N. J. Am. Chem. Soc. 129 (2007) 15513-15525
42. Price K.E., Broadwater S.J., Jung H.M., and McQuade D.T. Org. Lett. 7 (2005) 147-150
43. Price K.E., Broadwater S.J., Walker B.J., and McQuade D.T. J. Org. Chem. 70 (2005) 3980-3987
44. Roy D., and Sunoj R.B. Org. Lett. 9 (2007) 4873-4876
45. Amarante G.W., Milagre H.M.S., Vaz B.G., Ferreira B.R.V., Eberlin M.N., and Coelho F. J. Org. Chem. 74 (2009) 3031-3037
46. Amarante G.W., Benassi M., Milagre H.M.S., Braga A.C.C., Maseras F., Eberlin M.N., and Coelho F. Chem.-Eur. J. 15 (2009) 12460-12469
47. For examples for the use of MBH adducts as substrate for natural products synthesis, see:
48. Coelho F., Veronese D., Pavam C.H., de Paula V.I., and Buffon R. Tetrahedron 62 (2006) 4563-4572
49. Perez R., Veronese D., Coelho F., and Antunes O.A.C. Tetrahedron Lett. 47 (2006) 1325-1328
50. Silveira G.P.D., and Coelho F. Tetrahedron Lett. 46 (2005) 6477-6481
51. Reddy L.J., Fournier J.F., Reddy B.V.S., and Corey E.J. Org. Lett. 7 (2005) 2699-2701
52. Almeida W.P., and Coelho F. Tetrahedron Lett. 44 (2003) 937-940
53. Feltrin M.A., and Almeida W.P. Synth. Commun. 33 (2003) 1141-1146
54. Dunn P.J., Fournier J.F., Hughes M.L., Searle P.M., and Wood A.S. Org. Process Res. Dev. 7 (2003) 244-253
55. Rossi R.C., and Coelho F. Tetrahedron Lett. 42 (2002) 2797-2800
56. Mateus C.R., Feltrin M.P., Costa A.M., Coelho F., and Almeida W.P. Tetrahedron 57 (2001) 6901-6908
57. Iwabuchi Y., Furukawa M., Esumi T., and Hatakeyama S. Chem. Commun. (2001) 2030-2031
58. Mateus C.R., and Coelho F. J. Braz. Chem. Soc. 16 (2005) 386-396
59. McCauley J.A., Nagasawa K., Lander P.A., Mischke S.G., Semones M.A., and Kishi Y. J. Am. Chem. Soc. 120 (1998) 7647-7648
60. Coelho F., Depres J.P., Brocksom T.J., and Greene A.E. Tetrahedron Lett. 30 (1989) 565-566
61. For recent examples of the use of MBH adducts as starting materials for heterocycles synthesis, see:
62. Vaithiyanathan V., Selvakumar K., and Shanmugam P. Synlett (2009) 1591-1596
63. Ravinder M., Sadhu P., Sarathi R., and Vaidya J. Tetrahedron Lett. 50 (2009) 4229-4232
64. Zhong W., Lin F., Chen R., and Su W. Synthesis (2009) 2333-2340
65. Narender P., Ravinder M., Sadhu P.S., China Raju B., Ramesh C., and Jayathirtha Rao V. Helv. Chim. Acta 92 (2009) 959-966
66. Bakthadoss M., and Sivakumar N. Synlett (2009) 1014-1018
67. Pirovani R.V., Ferreira B.R.V., and Coelho F. Synlett (2009) 2333-2337
68. Meng X., Huang Y., and Chen R. Org. Lett. 11 (2009) 137-140
69. Kim K.H., Lee H.S., and Kim J.N. Tetrahedron Lett. 50 (2009) 1249-1251
70. Han E.-G., Kim H.J., and Lee K.-J. Tetrahedron 65 (2009) 9616-9625
71. Lee H.S., Kim S.H., Gowrisankar S., and Kim J.N. Tetrahedron 64 (2008) 7183-7190
72. He L., Jian T.-Y., and Ye S. J. Org. Chem. 72 (2007) 7466-7468
73. Lee H.S., Kim J.M., and Kim J.N. Tetrahedron Lett. 48 (2007) 4119-4122
74. Park D.Y., Gowrisankar S., and Kim J.N. Bull. Korean Chem. Soc. 26 (2005) 1440-1442
75. Chem. Abstr. 144 (2005) 350460
76. Lee C.G., Lee K.Y., Lee S., and Kim J.N. Tetrahedron 61 (2005) 1493-1499
77. Basavaiah D., Rao J.S., and Reddy R.J. J. Org. Chem. 69 (2004) 7379-7382
78. Coelho F., Veronese D., Lopes E.C.S., and Rossi R.C. Tetrahedron Lett. 44 (2003) 5731-5735
79. O'Dell D.K., and Nicholas K.M. J. Org. Chem. 68 (2003) 6427-6430
80. Kim J.N., and Lee K.Y. Curr. Org. Chem. 6 (2002) 627-645
81. Kim J.N., Chung Y.M., and Im Y.J. Tetrahedron Lett. 43 (2002) 6209-6221
82. Basavaiah D., Reddy R.M., Kumaragurubaran N., and Sharada D.S. Tetrahedron 58 (2002) 3693-3697
83. Kim J.N., Lee H.J., Lee K.Y., and Kim H.S. Tetrahedron Lett. 42 (2001) 3737-3740
84. Hong W.P., and Lee K.-J. Synthesis (2006) 963-968
85. Kim J.N., Lee K.Y., Kim H.S., and Kim T.Y. Org. Lett. 2 (2000) 343-345
86. For examples of ESI-MS monitoring of key organic reactions see:
87. Eberlin M.N., Meurer E.C., Santos L.S., and Pilli R.A. Org. Lett. 5 (2003) 1391-1394
88. Sabino A.A., Machado A.H.L., Correia C.R.D., and Eberlin M.N. Angew. Chem., Int. Ed. 43 (2004) 2514-2518
89. Pla-Quintana A.P., and Roglans A. ARKIVOC IX (2005) 51-62
90. Furmeier S., Griep-Raming J., Hayen A., and Metzger J.O. Chem.-Eur. J. 11 (2005) 5545-5554
91. Masllorens J., Moreno-Manas M., Pla-Quintana A., and Roglans A. Org. Lett. 5 (2003) 1559-1561
92. Jayakannan M., van Dongen J.L.J., and Janssen R.A.J. Macromolecules 34 (2001) 5386-5393
93. Aliprantis A.O., and Canary J.W. J. Am. Chem. Soc. 116 (1994) 6985-6986
94. De Souza R.O.M.A., da Penha E.T., Milagre H.M.S., Garden S., Esteves P.M., Eberlin M.N., and Antunes O.A.C. Chem.-Eur. J. 15 (2009) 9799-9804
95. In: Santos L.S. (Ed). Reactive Intermediates (2010), Wiley-VCH, Weinheim
96. Amarante G.W., Benassi M., Sabino A.A., Esteves P.M., Coelho F., and Eberlin M.N. Tetrahedron Lett. 47 (2006) 8427-8431
97. Coelho F., Almeida W.P., Veronese D., Mateus C.R., Lopes E.C.S., Rossi R.C., Silveira G.P.C., and Pavam C.H. Tetrahedron 58 (2002) 7437-7447
98. Almeida W.P., and Coelho F. Tetrahedron Lett. 39 (1998) 8609-8612
99. Lee K.Y., Kim J.M., and Kim J.N. Tetrahedron 59 (2003) 385-390
100. Said S.A., and Fiksdahl A. Tetrahedron: Asymmetry 12 (2001) 893-896
101. Ordoukhanian P., and Taylor J.-S. J. Am. Chem. Soc. 117 (1995) 9570-9571
102. Yoo B.W., Choi J.W., and Yoon C.M. Tetrahedron Lett. 47 (2006) 125-126
103. Rosenthal J., and Schuster D.I. J. Chem. Educ. 80 (2003) 679-690
104. Blanskepoor R.L., and Pearson A.J. J. Chem. Educ. 84 (2007) 697-698
105. Lager E., Andersson P., Nilsson J., Pettersson I., Nielsen E.Ø., Nielsen M., Sterner O., and Liljefors T. J. Med. Chem. 49 (2006) 2526-2533
106. Mazuel C. Norfloxacin. In: Florey K. (Ed). Analytical Profiles of Drug Substances (1991), Academic, San Diego 557-600