An efficient domino reaction in ionic liquid: Synthesis and biological evaluation of some pyrano- and thiopyrano-fused heterocycles

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 6, 2013, Pages 1656-1661

  Parmar, Narsidas J ^a   Patel, Rikin A ^a   Parmar, Bhagyashri D ^a   Talpada, Navin P ^a  

^a SARDAR PATEL UNIVERSITY   (India)

Author keywords

Domino Knoevenagel hetero Diels Alder; Ionic liquid; Pyranocoumarin; Thiopyranoquinoline; Triethylammonium acetate

Indexed keywords

2 ALKENSULFANYL QUINOLINE 3 CARBALDEHYDE; 7 OLEFINOXY COUMARIN 8 CARBALDEHYDE; ALDEHYDE DERIVATIVE; AMPICILLIN; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTIOXIDANT; CIPROFLOXACIN; COUMARIN DERIVATIVE; IONIC LIQUID; NORFLOXACIN; PYRAZOLONE DERIVATIVE; QUINOLONE DERIVATIVE; TRIETHYLAMMONIUM ACETATE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; BACILLUS SUBTILIS; CATALYST; CLOSTRIDIUM TETANI; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; KNOEVENAGEL CONDENSATION; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SALMONELLA TYPHI; STREPTOCOCCUS PNEUMONIAE; VIBRIO CHOLERAE;

ALDEHYDES; ANTI-BACTERIAL AGENTS; COUMARINS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HETEROCYCLIC COMPOUNDS; IONIC LIQUIDS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; PYRANS; PYRAZOLONES; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

ALNUS; BACILLUS SUBTILIS; CLOSTRIDIUM TETANI; ESCHERICHIA COLI; MYCOBACTERIUM TUBERCULOSIS; NEGIBACTERIA; POSIBACTERIA; SALMONELLA TYPHI; STREPTOCOCCUS PNEUMONIAE; VIBRIO CHOLERAE;

EID: 84874654274     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.01.079     Document Type: Article

References (118)

1. M. Freemantle An Introduction to Ionic Liquids 2010 RSC Publishing Cambridge
2. N.V. Plechkova, and K.R. Seddon Chem. Soc. Rev. 37 2008 123 and references cited therein
3. H. Zhao Chem. Eng. Commun. 193 2006 1660
4. N. Isambert, M.D.M. Sanchez, J.C. Plaquevent, Y. Genisson, J. Rodriguez, and T. Constantieux Chem. Soc. Rev. 40 2011 1347
5. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2002 Wiley-VCH Weinheim
6. T. Welton Chem. Rev. 99 1999 2071
7. H.M. Meshram, P.N. Reddy, P. Vishnu, K. Sedashir, and J.S. Yadav Tetrahedron Lett. 47 2006 991
8. H. Gong, C. Cai, N. Yang, L. Yang, and Q. Fan J. Mol. Catal. A: Chem. 249 2006 236
9. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3773
10. S. Shahoo, T. Joseph, and S.B. Halligudi J. Mol. Catal. A: Chem. 244 2006 179
11. F.C. Liu, M.B. Abrams, R.T. Baker, and W. Tumas Chem. Commun. 2001 433
12. E.D. Bates, R.D. Mayton, I.J. Ntai, and H. Davis J. Am. Chem. Soc. 124 2002 926
13. M.J. Earle, P.B. McCormac, and K.R. Seddon Green Chem. 2 2000 261
14. G.A. Olah, T. Mathew, A. Goeppert, B. Torok, I. Bucsi, X.Y. Li, Q. Wang, E.R. Marinez, P. Batamack, R. Aniszfeld, and G.K.S. Prakash J. Am. Chem. Soc. 127 2005 5964
15. J.M. Khurana, and D. Magoo Tetrahedron Lett. 50 2009 7300
16. D. Chaturvedi Curr. Org. Synth. 8 2011 438
17. J.R. Harjani, S.J. Nara, and M.M. Salunkhe Tetrahedron Lett. 43 2002 1127
18. V.V. Namboodiri, and R.S. Varma Chem. Commun. 2002 342
19. R. Sheldon Chem. Commun. 2001 2399
20. F. Zhang, D.Q. Xu, S.P. Luo, B.Y. Liu, X.H. Du, and Z.Y. Xu Chem. Res. 24 2004 773
21. A. Kamal, and G. Chouhan Adv. Synth. Catal. 346 2004 579
22. H.P. Nguyen, S. Znifeche, and M. Baboulene Synth. Commun. 34 2004 2085
23. H. Valizadeh, and S. Vaghefi Synth. Commun. 39 2009 1666
24. D.V. Jawale, U.R. Pratap, A.A. Mulay, J.R.M. Ramrao, and A. Mane J. Chem. Sci. 123 2011 645
25. J.F. Dubreuil, and J.P. Bazureau Tetrahedron Lett. 41 2000 7351
26. B.R. Ranu, and S. Banerjee Org. Lett. 7 2005 3049
27. Y. Hikaru, O. Hiroshi, and T. Takeo Org. Biomol. Chem. 7 2009 3657
28. S. Fang, Y. Hua, G. Ge, and R. Gang Chin. Chem. Lett. 16 2005 321
29. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis Vol. 1 2008 Wiley-VCH Weinheim
30. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis Vol. 2 2008 Wiley-VCH Weinheim
31. I. Parvulescu, and C. Hardacre Chem. Rev. 2007 107
32. J. Durand, E. Teuma, and M.C.R. Gómez Chimie 10 2007 152
33. S.G. Zlotin, and N.N. Makhova Mendeleev Commun. 20 2010 63
34. S.G. Zlotin, and N.N. Makhova Usp. Khim. 79 2010 603
35. L.F. Tietze Chem. Rev. 96 1996 115
36. L.F. Tietze, and Y.F. Zhou Angew. Chem., Int. Ed. 38 1999 2045
37. H. Pellissier Tetrahedron 62 2006 1619
38. N.T. Dat, J. Lee, K. Lee, Y. Hong, Y.H. Kim, and J.J. Lee J. Nat. Prod. 71 2008 1696
39. D.J. Kwok, R.N. Farr, and D.J. Daves J. Org. Chem. 56 1991 3711
40. B.B. Sinder, and Q.J. Lu J. Org. Chem. 61 1996 2839
41. H.N. Borah, M.L. Deb, R.C. Boruach, and P. Bhuyan Tetrahedron Lett. 46 2005 3391
42. K.C. Majumdar, A. Taher, and K. Ray Tetrahedron Lett. 50 2009 3889
43. R.D. Murray, J. Mendez, and S.A. Brown The Natural Coumarins: Occurrence, Chemistry and Biochemistry 1982 John Wiley and Sons New York, NY 227
44. S. Maity, S.A. Khan, and S. Ahmad Int. J. Pharm. Sci. 2 2012 87
45. Y.L. Wen, Q.X. Xu, M.Z. Dong, F.S. Yu, and H.Y. Zhi Molecules 17 2012 5497
46. A.G. Megbas, H.F. Abdullah, E.W. Abd, and A.M. Mostafa Lett. Drug Des. & Discovery 9 2012 459
47. S.G. Kini, S. Choudhary, and M. Mubeen J. Comput. Methods Mol. Des. 2 2012 51
48. J.L. Marco, and M.C. Carreiras J. Med. Chem. 6 2003 518
49. R. Argotle, A. Ramirez, G. Rodriquez, M.H. Rodriguez, and C. Gonzalez J. Nat. Prod. 69 2006 1442
50. H.S. Seleem, G.A. El-Inany, B.A. El-Shetary, and M.A. Mousa Chem. Cent. J. 5 2011 2
51. M.A. Bhat, and M.A. Al-Omar Acta Pol. Pharm. Drug Res. 68 2011 889
52. M.S. Mustafa, M.M. El-Abadelah, M.A. Zihlif, and R.G. Naffa Molecules 16 2011 4305
53. Kontogiorgis C.; Desti A.; Hadjipavlou-Litina D. Coumarin-Based Drug: a Patent Review (2008-present); Expert Opin. Ther. Pat. 2012, 22, 437. http://dx.doi.org/10.1517/13543776, 2012, 678835.
54. V.R. Solomon, and H. Lee Curr. Med. Chem. 18 2011 1488
55. J.L. Wang, D. Liu, Z.J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, and Z. Huang Proc. Natl. Acad. Sci. U.S.A. 97 2000 7124
56. M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, and A.E.Z. Rashad Naturforsch C 61 2006 1
57. Z.H. Ismail, G.M. Aly, M.S. El-Degwi, H.I. Heiba, and M.M. Ghorab Egypt. J. Biotech. 13 2003 73
58. F.M. Abdelrazek, P. Metz, N.H. Metwally, and S.F. El-Mahrouky Arch. Pharm. 339 2006 456
59. D.A. Eiznhamer, T. Creagh, D.T. Tolbert, J. Giltner, and B. Dutta HIV Clin. Trials 6 2002 435
60. A. Saklani, and S.K. Kutty Drug Discovery Today 13 2008 161
61. M. Suzuki, Y. Li, and P.C. Smith Drug Metab. Dispos. 33 2005 1588
62. H.Z. Chun, Z. Ting, X. Lan, and Y. Jing Chin. Chem. Lett. 16 2005 1297
63. Q.X. Shi, Y. Xin, C. Ying, X. Peng, and Q. Keduo Bioorg. Med. Chem. 18 2010 7203
64. M. Eleni, M. Prokopios, S. Mitaku, S. Leandros, and E. Chinou J. Nat. Prod. 68 2005 78
65. A. Gunatilaka, and D. Kingston J. Nat. Prod. 57 1994 518
66. C.Y. Duh, S.K. Wang, and Y.C. Wu Phytochemistry 30 1991 2812
67. C.Y. Duh, S.K. Wang, and Y.C. Wu Phytochemistry 1992 1829 31
68. L. Damien, D.K. Prado, and J. Kasenene J. Nat. Prod. 74 2011 2286
69. B. Kalluraya, J. Nayak, A. Adhikari, K.V. Sujith, N. Sucheta, and M.W. Shetty Phosphorus, Sulfur Silicon 2008 1870 183
70. J.E. Charris, J.N. Domínguez, N. Gamboa, J.R. Rodrigues, and J.E. Angel Eur. J. Med. Chem. 40 2005 875
71. V.K. Bhovi, Y.D. Bodke, S. Biradar, B.E. Kumar, and S. Umesh Phosphorus, Sulfur Silicon 185 2010 110
72. Z. Xie, K. Chai, H. Piao, K. Kwak, and Z. Quan Bioorg. Med. Chem. Lett. 15 2005 4803
73. F.R. Nawaz Khan, and S.M. Roopan Arkivoc 13 2009 161
74. R.A. Corral, and O. Orazi Tetrahedron Lett. 7 1967 583
75. L. Puricelli, G. Innocenti, M.G. Delle, R. Caniato, R. Filippini, and E.M. Cappelletti Nat. Prod. Lett. 16 2002 95
76. Lesage, A. S. J.; Bischoff, F. P.; Janseen, C. G. M.; Lavreysen, H. WO 03082350; 2003.
77. O. Tabarrini, V. Cecchetti, A. Temperini, and E. Filipponi Bioorg. Med. Chem. 9 2001 2921
78. M.J. Khoshkholgh, M.R. Hosseindokht, and S. Balalaie Helv. Chim. Acta 95 2012 52
79. A. Ghoshal, A.R. Sarkar, R.S. kumaran, and S. Hegde Tetrahedron Lett. 53 2012 1748
80. S. Majumder, and P.J. Bhuyan Tetrahedron Lett. 53 2012 137
81. A. Mishra, N. Rastogi, and S. Batra Tetrahedron 68 2012 2146
82. B.V.S. Reddy, B. Divya, M. Swain, T.P. Rao, and J.S. Yadav Bioorg. Med. Chem. Lett. 2012 1995 22
83. S. Maiti, S.K. Panja, and C. Bandyopadhyay Tetrahedron 66 2010 7625
84. J.S. Yadav, B.V.S. Reddy, D. Narsimhaswamy, and P.N. Lakshmi Tetrahedron Lett. 45 2004 3493
85. L.F. Tietze, and U. Beifuss Angew. Chem., Int. Ed. 32 1993 131
86. H. Pellissier Tetrahedron 62 2006 2143
87. L.F. Tietze, and N. Rackelmann Pure Appl. Chem. 2004 1967 76
88. L.F. Tietze, T. Kinzel, and C.C. Brazel Acc. Chem. Res. 42 2009 367
89. D. Enders, C. Wang, and J.W. Bats Angew. Chem., Int. Ed. 47 2008 7539
90. Z. Zhang, Q. Zhang, S. Sun, T. Xiong, and Q. Liu Angew. Chem., Int. Ed. 46 2007 1726
91. D. Enders, C. Grondal, and M.R.M. Hutt Angew. Chem., Int. Ed. 46 2007 1570
92. A.K. Yadav, S. Peruncheralathan, H. Ila, and H. Junjappa J. Org. Chem. 72 2007 1388
93. N.J. Parmar, S.B. Teraiya, R.A. Patel, and N.P. Talpada Tetrahedron Lett. 52 2011 2853
94. J. Jayashankaran, R.S. Manian, and R. Rghavachary Tetrahedron Lett. 47 2006 2265
95. N.J. Parmar, R.A. Patel, S.B. Teraiya, D. Sharma, and V.K. Gupta RSC Adv. 2 2012 3069
96. M. Bakthadoss, G. Sivakumar, and D. Kannan Org. Lett. 11 2009 4466
97. K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025
98. V.R. Choudhary, A. Dhar, P. Jana, R. Jha, and B.S. Uphade Green Chem. 7 2005 768
99. N. Deka, and A.M. Mariotte Green Chem. 3 2001 263
100. G. Yanlong, Z. Juan, D. Zhiying, and D. Youquan Adv. Synth. Catal. 347 2005 512
101. B. Movassagh, and P. Shaygan Arkivoc 7 2006 130
102. H.S. Rao, and S. Jothilingam J. Chem. Sci. 117 2005 323
103. N.J. Parmar, B.R. Pansuriya, H.A. Barad, K. Rajni, and V.K. Gupta Bioorg. Med. Chem. Lett. 22 2012 4075
104. N.J. Parmar, H.A. Barad, S.B. Teraiya, B.R. Pansuriya, K. Rajni, and V.K. Gupta Bioorg. Med. Chem. Lett. 22 2012 3816
105. Parmar, N. J.; Teraiya, S. B.; Barad, H. A.; Sharma, D.; Gupta, V. K. Synth. Commun. 2012 http://dx.doi.org/10.1080/00397911.2011.652755 (published online 17 may 2012).
106. N.J. Parmar, B.R. Pansuriya, B.M. Labana, T.R. Sutariya, R. Kant, and V.K. Gupta Eur. J. Org. Chem. 2012 5953
107. Parmar, N. J.; Pansuriya, B. R.; Barad, H. A.; Parmar, B. D., Kant, R.; Gupta, V. K. Monatsh Chem. http://dx.doi.org/10.1007/s00706-012-0873-7 (published online).
108. A.K. Verma, P. Attri, V. Chopra, R.K. Tiwari, and R. Chandra Monatsh Chem. 139 2008 1041
109. R. Balaskar, S. Gavade, M. Mane, P. Pabrekar, M. Shingare, and D. Mane Lett. Org. Chem. 8 2011 282
110. D. Kumar, and J.S. Sandhu Rasayan J. 2 2009 937
111. H. Mamoru, M. Morimura, and Y. Hayakawa Nucleosides Nucleotides Nucleic Acids 24 2005 585
112. H. Xiaoke, Z. Liangfang, W. Xueqin, G. Bin, X. Jiaquan, L. Guiying, and H. Changwei J. Mol. Catal. A: Chem. 342 2011 41
113. R. Balaskar, S. Gavade, M. Mane, P. Pabrekar, M. Shingare, and D. Mane Chin. Chem. Lett. 21 2010 1175
114. L. Knorr Chem. Ber. 16 1883 2597
115. Shadomy, S.; Pfaller, M. A. Laboratory Studies with Antifungal Agents: Susceptibility Tests and Quantitation in Body Fluids. In Manual of Clinical Microbiology, 5th ed.; Balows, A., Hausler, W. J., Hermann, K. L., Isenberg, H. D., Shadomy H. J., Eds.; Washington DC, 1991; Chapter 117, p 1173.
116. National Committee for Clinical Laboratory Standards. Methods for Dilutionantimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 5th ed.; Approved Standard (M7A5); National Committee for Clinical Laboratory Standards: Wayne, PA, 2000.
117. A. Rattan Antimicrobials in Laboratory Medicine 2000 Churchill BI Livingstone New Delhi p 85
118. I.F.F. Benzie, and J.J. Strain Anal. Biochem. 239 1996 70