Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents

Journal of Chemical Sciences

Volumn 124, Issue 3, 2012, Pages 609-624

  Praveen, C ^a   Nandakumar, A ^a   Dheenkumar, P ^b   Muralidharan, D ^a   Perumal, P T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

^b EGS Pillay College of Pharmacy   (India)

Author keywords

Analgesic activity.; Benzothiazoles; Benzoxazoles; Microwave; One pot synthesis

Indexed keywords

CHEMISTRY; MICROWAVES;

ANALGESIC ACTIVITY; BENZOTHIAZOLES; BENZOXAZOLE; BENZOXAZOLES; CYCLOCONDENSATION; MICROWAVE ASSISTED; MICROWAVE ASSISTED SYNTHESIS; ONE-POT SYNTHESIS;

LIBRARIES;

EID: 84863701208     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-012-0251-3     Document Type: Article

References (126)

1. Temiz O, Oren I, Sener E, Yalcin I and Ucarturk N 1998 Farmaco 53 337
2. Sato S, Kajiura T, Noguchi M, Takehan K, Kobayashi T and Tsuji T 2001 J. Antibiot. 54 102
3. Bradshaw T D, Shi D F, Schultz R J, Paull K D, Kelland L, Wilson A, Garner C, Fiebig H H, Wrigley S and StevensMF 1998 Br. J. Cancer 78 421
4. Craigo W A, LeSueur B W and Skibo E B 1999 J. Med. Chem. 42 3324
5. Gudmundsson K S, Tidwell J, Lippa N, Koszalka GW, van Draanen N, Ptak R G, Drach J C and Townsend L B 2000 J. Med. Chem. 43 2464
6. Chen J J, Wei Y, Drach J C and Townsend L B 2000 J. Med. Chem. 43 2449
7. Mann J, Baron A, Opoku-Boahen Y, Johansson E, Parkinson G, Kelland L R and Neidle S 2001 J. Med. Chem. 44 138
8. Kuhler T C, Swanson M, Christenson B, Klintenberg A-C, Lamm B, Fagerhag J, Gatti R, Olwegard-Halvarsson M, Shcherbuchin V, Elebring T and Sjostrom J-E 2002 J. Med. Chem. 45 4282
9. Katsura Y, Inoue Y, Nishino S, Tomoi M, Itoh H and Takasugi H 1992 Chem. Pharm. Bull. 40 1424
10. Koci J, Klimesova V, Waisser K, Kaustova J, Dahse H M and Mollmann U 2002 Bioorg. Med. Chem. Lett. 12 3275
11. Katsura Y, Inoue Y, Tomishi T, Itoh H, Ishikawa H and Takasugi H 1992 Chem. Pharm. Bull. 40 2432
12. Kashiyama E, Hutchinson I, Chua M S, Stinson S F, Phillips L R, Kaur G, Sausville E A, Bradshaw T D, Westwell A D and Stevens M F G 1999 J. Med. Chem. 42 4172
13. Lau C K, Dufresne C, Gareau Y, Zamboni R, Labelle M, Young R N,Metters KM, Rochette C, Sawyer N, Slipetz D M, Charette L, Jones T, McAuliffe M, McFarlane C and Ford-Hutchinson A W 1995 Bioorg. Med. Chem. 5 1615
14. Bergman J M, Coleman P J, Cox C, Hartman G D, Lindsley C, Mercer S P, Roecker A J and Whitman D B 2006 PCT Int. Appl. WO 2006127550
15. Nagel A A, Liston D R, Jung S, Maher M, Vincent L A, Chapin D, Chen Y L, Hubbard S, Ives J L and Jones S B 1995 J. Med. Chem. 38 1084
16. Chua M-S, Shi D-F, Wrigley S, Bradshaw T D, Hutchinson I, Shaw P N, Barrett D A, Stanley L A and Stevens M F G 1999 J. Med. Chem. 42 381
17. hutchinson I, Chua M-S, Browne H L, Trapani V, Bradshaw T D, Westwell A D and Stevens M F G 2001 J. Med. Chem. 44 1446
18. Leng W, Zhou Y, Xu Q and Liu J 2001 Macromolecules 34 4774
19. Hutchinson I, Jennings S A, Vishnuvajjala B R, Westwell A D and Stevens M F G 2002 J. Med. Chem. 45 744
20. Shi D-F, Bradshaw T D, Wrigley S, McCall C J, Lelieveld P, Fichtner I and Stevens M F G 1996 J. Med. Chem. 39 3375
21. Beebe X, Wodka D and Sowin T J 2001 J. Comb. Chem. 3 360
22. Hari A, Karan C, Rodrigues W C and Miller B L 2001 J. Org. Chem. 66 991
23. Pottorf R S, Chadha N K, Katkevics M, Ozola V, Suna E, Ghane H, Regberg T and Player M R 2003 Tetrahedron Lett. 44 175
24. Naitoh T, Mishima M, Kawaguchi S, Matsui K, Andoh T, Kagei K, Kakiki M, Yuzuriha T and Horie T 1997 Xenobiotica 27 1053
25. Kagaya T, Kajiwara A, Nagato S, Akasaka K and Kubota A 1996 J. Pharmacol. Exp. Ther. 278 243
26. Hadjipavlou-Litina D J and Geronikaki A A 1997 Drug Des. Discov. 15 199
27. Gong B, Hong F, Kohm C, Bonham L and Klein P 2004 Bioorg. Med. Chem. Lett. 14 1455
28. Mylari B L, Larson E R, Beyer T A and Zembrowski W J, Aldinger C E, Dee M F, Siegel T W and Singleton D H 1991 J. Med. Chem. 34 108
29. Kotani T, Nagaki Y, Ishii A, Konishi Y, Yago H, Suehiro S, Okukado N and Okamoto K 1997 J. Med. Chem. 40 684
30. Paramashivappa R, Kumar P P, Rao P V S and Rao A S 2003 Bioorg. Med. Chem. Lett. 13 657
31. Surgue M F, Gautheron P, Schmitt C, Viader M P, Conquet P, Smith R L, Share N N and Stone C A 1985 J. Pharmacol. Exp. Ther. 232 534
32. Sohn S K, Chang M S, Choi W S, Kim K B, Woo T W, Lee S B and Chung Y K 1999 Can. J. Physiol. Pharmacol. 77 330
33. Phoon C W, Ng P Y, Ting A E, Yeo S L and Sim M M 2001 Bioorg. Med. Chem. Lett. 11 1647
34. Caccese R G, DiJoseph J F, Scotnicki J S, Borella L E and Adams L M 1991 Agents Actions 34 223
35. Black C, Deschenes D, Gagnon M, Lachance N, Legar S, C Li S and Oballa R M 2006 PCT Int. Appl. WO 2006122200 A1 20061116
36. Hall I H, Peaty N J, Henry J R, Easmon J, Heinisch G and Purstinger G 1999 Arch. Pharm. (Weinheim) 332 115
37. Bénéteau V, Besson T, Guillard J, Léonce S and Pfeiffer B 1999 Eur. J. Med. Chem. 34 1053
38. Hutchinson I, Bradshaw T D, Stevens M F G and Westwell A D 2003 Bioorg. Med. Chem. Lett. 13 471
39. Palmer P J, Trigg R B and Warrington J V 1971 J. Med. Chem. 14 248
40. Ali A, Taylor G E and Graham D W 2001 PCT Int. Appl. WO 2001028561
41. Ivanov S K and Yuritsyn V S 1971 Neftekhimiya 11 99
42. Ivanov S K and Yuritsyn V S 1971 Chem. Abstr. 74 124487m
43. Benazzouz A, Boraud T, Dubédat P, Boireau A, Stutzmann J-M and Gross C 1995 Eur. J. Pharmacol. 284 299
44. Jimonet P, Audiau F, Barreau M, Blanchard J-C, Boireau A, Bour Y, Coléno M-A, Doble A, Doerflinger G, Huu C D, Donat M-H, Duchesne J M, Ganil P, Guérémy C, Honoré E, Just B, Kerphirique R, Gontier S, Hubert P, Laduron P M, Blevec J L, Meunier M, Miquet J-M, Nemecek C, Pasquet M, Piot O, Pratt J, Rataud J, Reibaud M, Stutzmann J-M and Mignani S 1999 J. Med. Chem. 42 2828
45. McKee M L and Kerwin S M 2008 Bioorg. Med. Chem. 16 1775
46. Oksuzoglu E, Tekiner-Gulbas B, Alper S, Temiz-Arpaci O, Ertan T, Yildiz I, Diril N, Sener-Aki E and Yalcin I 2008 J. Enzyme Inhib. Med. Chem. 23 37
47. Oksuzoglu E, Temiz-Arpaci O, Tekiner-Gulbas B, Eroglu H, Sen G, Alper S, Yildiz I, Diril N, Aki-Sener E and Yalcin I 2007 Med. Chem. Res. 16 1
48. H Potashman M, Bready J, Coxon A, DeMelfi T M, DiPietro Jr L, Doerr N, Elbaum D, Estrada J, Gallant P, Germain J, Gu Y, Harmange J-C, Kaufman S A, Kendall R, Kim J L, Kumar G N, Long A M, Neervannan S, Patel V F, Polverino A, Rose P, Van der Plas S, Whittington D, Zanon R and Zhao H 2007 J. Med. Chem. 50 4351
49. Huang S-T, Hsei I-J and Chen C 2006 Bioorg. Med. Chem. 14 6106
50. Deluca M R and Kerwin S M 1997 Tetrahedron Lett. 38 199
51. Edwards P D, Meyer E F, Vijayalakshmi J, Tuthill P A, Andisik D A, Gomes B and Strimpler A 1992 J. Am. Chem. Soc. 114 1854
52. Sato Y, Yamada M, Yoshida S, Soneda T, Ishikawa M, Nizato T, Suzuki K and Konno F 1998 J. Med. Chem. 41 3015
53. Rodriguez A D, Ramrez C, Rodiguez I I and Gonzalez E 1999 Org. Lett. 1 527
54. Ben-Alloum A, Bakkas S and Soufiaoui M 1997 Tetrahedron Lett. 38 6395
55. Ranu B C, Jana R and Dey S S 2004 Chem. Lett. 33 274
56. Mourtas S, Gatos D and Barlos K 2001 Tetrahedron Lett. 42 2201
57. Itoh T, Nagata K, Ishikawa H and Ohsewa A 2004 Heterocycles 63 2769
58. Niralwad K S, Shingate B B and Shingare M S 2010 Bull. Korean Chem. Soc. 31 981
59. Al-Qalaf F, Mekheimer R A and Sadek K U 2008 Molecules 13 2908
60. Londhe B S, Pratap U R, Mali J R and Mane R A 2010 Bull. Korean Chem. Soc. 31 2329
61. Chen C and Chen Y-J 2004 Tetrahedron Lett. 45 113
62. Hutchinson I, StevensMF G andWestwell A D 2000 Tetrahedron Lett. 41 425
63. Spitulnik M J 1976 Synthesis 730
64. Mu X-J, Zou J-P, Zeng R-S and Wu J-C 2005 Tetrahedron Lett. 46 4345
65. Bose D S and Idrees M 2006 J. Org. Chem. 71 8261
66. Paul S, Gupta M and Gupta R 2002 Synth. Commun. 32 3541
67. Shirinian V Z, Melkova S Yu, Belenkii L I, Krayushkin M M and Zelinsky N D 2000 Russ. Chem. Bull. 49 1859
68. Zhong W H, Zhang Y M and Chen X Y 2001 J. Indian Chem. Soc. 78 316
69. Roe A and TuckerWP 1965 J. Heterocycl. Chem. 2 148
70. Stanetty P and Krumpark B 1996 J. Org. Chem. 61 5130
71. Ares J J 1991 Synth. Commun. 21 625
72. Majo V J, Prabhakaran J, Mann J J and Kumar J S D 2003 Tetrahedron Lett. 44 8535
73. Tale R H 2002 Org. Lett. 4 1641
74. Hein DW, Alheim R J and Leavitt J J 1957 J. Am. Chem. Soc. 79 427
75. Itoh T and Mase T 2007 Org. Lett. 9 3687
76. Terashima M and Ishii M 1982 Synthesis 1484 and references cited therein
77. Varma R S, Saini R K and Prakash O 1997 Tetrahedron Lett. 38 2621
78. Prakash O, Pannu K and Kumar A 2006 Molecules 11 43
79. Varma R S and Kumar D 1998 J. Heterocycl. Chem. 35 1539
80. Park K H, Jun K, Shin S R and Oh S W 1996 Tetrahedron Lett. 37 8869
81. Srivastava R G and Venkataramani P S 1988 Synth. Commun. 18 1537
82. Nakagawa K, Onoue H and Sugita J 1964 Chem. Pharm. Bull. 12 1135
83. Stephens F F and Bower J D 1949 J. Chem. Soc. 2971
84. Chang J, Zhao K and Pan S 2002 Tetrahedron Lett. 43 951
85. Talapatra S K, Chaudhuri P and Talapatra B 1980 Heterocycles 14 1279
86. Kidwai M, Bansal V, Saxena A, Aerry S and Mozumdar S 2006 Tetrahedron Lett. 47 8049
87. Kawashita Y, Nakamichi N, Kawabata H and HayashiM 2003 Org. Lett. 5 3713
88. Speier G 1987 J. Mol. Catal. 41 253
89. Haginiwa J, Higuchi Y and Ohtsuka H 1976 Yakugaku Zasshi 96 209
90. Huxley A 2006 Synlett 2658
91. Pottorf R S, Chadha N K, Katkevics M, Ozola V, Suna E, Ghane H, Regberg T and Player M R 2003 Tetrahedron Lett. 44 175
92. Bonnamour J and Bolm C 2008 Org. Lett. 10 2665
93. Chen Y and Xie N 2006 J. Photochem. Photobiol. A; Chem. 179 320
94. Chen Y and Zeng De X 2004 J. Org. Chem. 69 5037
95. Li Z-X, FuW-F, YuM-M, Zhao X-J and Chen Y 2007 Dyes Pigments 75 516
96. Tauer E and Grellmann K H 1981 J. Org. Chem. 46 4252
97. Grellmann K H and Tauer E 1967 Tetrahedron Lett. 8 1909
98. Chen W H and Pang Y 2009 Tetrahedron Lett. 50 6680
99. Gottumukkala A L, Derridj F, Djebbar S and Doucet H 2008 Tetrahedron Lett. 49 2926
100. Alagille D, Baldwin R M and Tamagnan G D 2005 Tetrahedron Lett. 46 1349
101. Nandurkar N S, Bhanushali M J, Bhor M D and Bhanage B M 2008 Tetrahedron Lett. 49 1045
102. Chen W, Wang M, Li P and Wang L 2011 Tetrahedron 67 5913
103. Praveen C, Kumar K H, Muralidharan D and Perumal P T 2008 Tetrahedron 64 2369
104. Praveen C, Kiruthiga P and Perumal P T 2009 Synlett 1990
105. Praveen C, Karthikeyan K and Perumal P T 2009 Tetrahedron 65 9244
106. Praveen C, Jegatheesan S and Perumal P T 2009 Synlett 2795
107. Praveen C, Kalyanasundaram A, and Perumal P T 2010 Synlett 777
108. Praveen C, Sagayaraj Y W and Perumal P T 2009 Tetrahedron Lett. 50 644
109. Praveen C, Parthasarathy K and Perumal P T 2010 Synlett 1635
110. Praveen C, Iyyappan C andPerumal P T 2010 Tetrahedron Lett. 51 4767
111. Praveen C, Dheenkumar P and Perumal P T 2010 Bioorg. Med. Chem. Lett. 20 7292
112. Praveen C and Perumal P T 2011 Synlett 521
113. Praveen C, Ayyanar A and Perumal P T 2011 Bioorg. Med. Chem. Lett. 21 4072
114. Praveen C, Ayyanar A and Perumal P T 2011 Bioorg. Med. Chem. Lett. 21 4170
115. Praveen C, Iyyappan C, Kumar K S K, Girija K and Perumal P T 2012 J. Chem. Sci. 124 451
116. Ghosh M N 2005 Fundamentals of Experimental Pharmacology, 3rd Edition, Hilton and Co., Kolkatta, 190-7
117. Kale S R and Kale R R 1994 Practical pharmacology and toxicology, 1st Edition, Nirali Prakashan, Pune, 56-57
118. Tohma H, Iwata M and Maegawa T, Kita Y 2002 Tetrahedron Lett. 43 9241
119. Boldron C, Aromi G, Challa G, Gamez P and Reedijk J 2005 Chem. Commun. 5808
120. Quideau S, Lebon M and Lamidey A-M 2002 Org. Lett. 4 3975
121. Fujioka H, Matsuda S, Horai M, Fujii E, Morishita M, Nishiguchi N, Hata K and Kita Y 2007 Chem. Eur. J. 13 5238
122. Correa A, Tellitu I, Dominguez E, and SanMartin R 2006 J. Org. Chem. 71 8316
123. Correa A, Tellitu I, Dominguez E and SanMartin R 2006 Tetrahedron 62 11100
124. Since, ethanol has a tan d value of 0.941; it was preferable over most of the polar solvents in microwave promoted reactions. For related discussions, see: Galema S A 1997 Chem. Soc. Rev. 26 233
125. Rajak H and Mishra P 2004 J. Sci. Ind. Res. 63 641
126. Vogel H G 2002 Drug discovery and evaluation-Pharmacological assays, 2nd Edition (New York: Springer) 697