Quinoxaline 1,4-dioxide: A versatile scaffold endowed with manifold activities

Current Medicinal Chemistry

Volumn 12, Issue 19, 2005, Pages 2259-2272

  Carta, A ^a   Corona, P ^a   Loriga, M ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Animal growth promoting; Antibacterial activity; Anticandida activity; Antimycobacterial activity; Antiprotozoal activity; Chemical syntheses and reactions; Hypoxia selective activity; Mutagenicity; Quinoxaline 1,4 dioxides; SAR studies

Indexed keywords

2 (2 QUINOXALINYL) DELTA2 1,3,4 THIADIAZOLIN 5 ONE QUINOXALINE 1,4 DIOXIDE; 2 (5 AMINO 1,3,4 THIADIAZOL 2 YL)QUINOXALINE 1,4 DIOXIDE; 2 ACETYL 3 METHYLQUINOXALINE 1,4 DIOXIDE; 2 BENZOYL 3 PHENYLQUINOXALINE 1,4 DIOXIDE; 2 BENZOYL 6,7 DICHLORO 3 PHENYLQUINOXALINE 1,4 DIOXIDE; 2,3 TETRAMETHYLQUINOXALINE 1,4 DIOXIDE; 3 METHYLQUINOXALINE 2 CARBOXALDEIDE; 6,7 DICHLORO 3 METHYL 2 PHENYLTHIOQUINOXALINE 1,4 DIOXIDE; 6,7 DIFLUORO 3 METHYL 2 (3,4 DIMETHOXYPHENYLTHIO)QUINOXALINE 1,4 DIOXIDE; 6,7 DIFLUORO 3 METHYL 2 PHENYLTHIOQUINOXALINE 1,4 DIOXIDE; 6,7 DIMETHYL 3 [4 (4' NITROPHENYL)PIPERAZIN 1 YL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 (4 NITROPHENYL) 2 QUINOXALINECARBONITRILE 1,4 DIOXIDE; 7 CHLORO(TRIFLUOROMETHYL) 3 (DIMETHYLAMINOPROPYL)AMINO 2 QUINOXALINECARBONITRILE 1,4 DIOXIDE; AMPICILLIN; ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; ANTIPROTOZOAL AGENT; CARBADOX; CHEMAPOL BENELUX; CHLORAMPHENICOL; CIADOX; METRONIDAZOLE; MICONAZOLE; NIFURTIMOX; OLAQUINDOX; QUINDOXIN; QUINOXALINE 1,4 DIOXIDE DERIVATIVE; QUINOXALINE DERIVATIVE; TRIPAZAMINE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL FOOD; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIFUNGAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; BACTERIAL INFECTION; BACTERIAL VIRULENCE; CHEMICAL REACTION; CLINICAL TRIAL; CYTOGENETICS; CYTOTOXICITY; DIARRHEA; DRUG STRUCTURE; DRUG SYNTHESIS; DYSENTERY; GENOTOXICITY; HUMAN; HYPOXIC CELL; IN VITRO STUDY; IN VIVO STUDY; LUNG NON SMALL CELL CANCER; MUTAGENESIS; NONHUMAN; PHOTOALLERGY; PHOTOCHEMISTRY; REVIEW; SALMONELLOSIS; SOLID TUMOR; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MUTAGENICITY TESTS; PHOTOCHEMISTRY; QUINOXALINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 23844472369     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867054864831     Document Type: Review

References (202)

1. Moore, P.R.; Evenson, A.; Luckey, T.D.; McCoy, E.; Elvehjem, C.A., Hart, E.B., J. Biol. Chem., 1946, 16, 437.
2. McIlwain, H. J. Chem. Soc., 1943, 322.
3. Landquist, J.K. J. Chem. Soc., 1953, 2816.
4. Stumm, J.; Niclas, H.J. J. Prakt. Chem., 1989, 331, 736.
5. Ley, K.; Eholzer, U.; Nast, R.; Metzger, K.G.; Fritsche, D., (Bayer A.-G.) Ger. Patent, 1975, U.S. patent 1,670,935;
6. Ley, K.; Eholzer, U.; Nast, R.; Metzger, K.G.; Fritsche, D., (Bayer A.-G.) Chem. Abstr., 1975, 83, 114485f.
7. Haddadin, M.J.; Kattan, A.M.A.; Issidorides, C.H. J. Org. Chem., 1985, 50, 129.
8. Kuhla, D.E. (Pfizer Inc.), 1977, U.S. patent 4,006,142;
9. Hebky, J.; Lupinek, V.; Sova, M.; Sevcik, B.; Broz, J. Chem. Abstr., 1979, 90 186997s.
10. Hebky, J.; Lupinek, V.; Sova, M.; Sevcik, B.; Broz, J.(SPOFA), Chem. Abstr., 1979, 90, 186997s.
11. Witte, W. Science, 1998, 279, 996.
12. Greife, H.A.; Berschauer, F. Übers Tierernährg, 1988, 16, 27.
13. Yen, J.T.; Nienaber, J.A.; Pond, W.G.; Varel, V.H. J. Nutr., 1985, 115, 970.
14. Yen, J.T.; Nienaber, J.A.; Pond, W.G. J. Anim. Sci., 1987, 65, 1243.
15. Yen, J.T.; Nienaber, J.A.; Hill, D.A., Pond, W.G. Proc. Soc. Exp. Biol. Med, 1989, 190, 393.
16. Yen, J.T; Nienaber, J.A.; Hill, D.A.; Pond, W.G. J. Anim. Sci., 1989, 67, 127.
17. Yen, J.T; Jensen, A.H.; Bajjalieh, N.H.; Ladwig, V.D. J. Anim. Sci., 1976, 42, 375.
18. Roof, M.D.; Mahan, D.C. J. Anim. Sci. 1982, 55, 1109.
19. Moser, B.D.; Peo, E.R., Jr.; Lewis, A.J. Nutr. Rep. Int., 1980, 22, 949.
20. Yen, J.T.; Nienaber, J.A. J. Anim. Sci., 1992, 70, 478.
21. Visek, W.J. J. Anim. Sci., 1978, 46, 1447.
22. Yen, J.T.; Killefer, J. J. Anim. Sci., 1987, 64, 923.
23. Yen, J.T.; Pond, W.G. J. Anim. Sci., 1990, 68, 4236.
24. Köhler, B.; Karch, H.; Schmidt, H. Microbiology, 2000, 146, 1085.
25. Suter, W.; Rosselet, A.; Knüsel, F. Antimicrob. Agents Chemother., 1978, 13, 770.
26. Linton, A.H.; Hedges, A.J.; Bennett, P.M. J. Appl. Bacteriol., 1988, 64, 311.
27. Corpet, D.E. Ann. Microbiol. (Paris) 1984, 135, 329.
28. Hedges, A.J.; Linton, A.H. J. Appl. Bacteriol., 1988, 64,429.
29. Sørensen, A.H.; Hansen, L.H.; Johannesen, E.; Sørensen, S.J. Antimicrob. Agents Chemother., 2003, 47, 798.
30. DANMAP. 1999. DANMAP 98-consumption of antimicrobialagents and occurence of antimicrobial resistance in bacteria from food animals, food and humans in Denmark.
31. Hestbjerg Hansen, L.; Johannesen, E.; Burmølle, M.; Sørensen, A.H.; S.J. Sørensen Antimicrob. Agents Chemother., 2004, 48, 3332.
32. Calnan, C.D. Contact Dermatitis, 1975, 1, 384.
33. Scott, K.W.; Dawson, T.A.J. Br. J. Dermatol., 1974, 90, 543.
34. Johnson, B.E.; Zaynoun, S.; Gardiner, J.; Frain-Bell, W. Br. J. Dermatol., 1975, 93, 21.
35. Zaynoun, S.; Johnson, B.E.; Frain-Bell, W. Contact Dermatitis, 1976, 2, 343.
36. Tucker, M.J., J. Natl. Cancer Inst., 1975, 55, 137.
37. Council Directive. OJ No L160/34, 20.6.1987: 1-2.
38. Bedello, P.G.; Goitre, M.; Cane, D.; Roncarolo, G. Contact Dermatitis, 1985, 12, 284.
39. Francalanci, S.; Gola, M.; Giorgini, S.; Muccinelli, A.; Sertoli, A. Contact Dermatitis, 1986, 15, 112.
40. Schauder, S.; Schröder, W.; Geier, J. Contact Dermatitis, 1996, 35, 344.
41. Barratt, M.D.; Brown, K.R. Toxicol. Lett., 1984, 1331.
42. Kochevar, I. Photochem. Photobiol., 1979, 30, 437.
43. Epstein, J. Arch. Dermatol., 1972, 106, 741.
44. Beyersbergen van Henegouwen, G.M.J. Arch. Toxicol. Suppl., 1988, 12, 3.
45. de Vries, H.; Bojarski, J.; Donker, A.A.; Bakri, A.; Beyersbergen van Henegouwen, G.M.J. Toxicology, 1990, 63, 85.
46. Voogd, C.E.; van der Stel, J.J.; Jacoba, J.J.J.A.A. Mutat. Res., 1980, 78, 233.
47. Negishi, T.; Tanaka, K.; Hayatsu, H. Chem. Pharm. Bull., 1980, 28, 1347.
48. Negishi, K.; Arao, Y.; Oka, N.; Hayatsu, H. Nucleic Acids Research, 1980, 8, 105.
49. Yoshimura, H.; Nakamura, M.; Koeda, T.; Yoshikawa, K. Mutat. Res., 1981, 90, 49.
50. Ohta, T.M.; Moriya, T.M.; Kaneda, Y.; Watanabe, K.; Miyazawa, T.; Sugiyama, F.; Shirasu, Y. Mutat. Res., 1980, 77, 21.
51. Beutin, L.; Preller, E.; Kowalski, B. Antimicrob. Agents Chemother., 1981, 20, 336.
52. Oud, J.L.; Reutlinger, A.H.H.; Branger, J., Mutat. Res., 1979, 68, 179.
53. Cihàk, R.; Srb, V.; Vontorkovà, M. Mutat. Res., 1983, 116, 129.
54. Cihàk, R.; Vontorkovà, M. Mutat. Res., 1983, 117, 311.
55. Gandalovicovà, D.; Polkornà, D.; Sykora, I. Acta Hyg. Epidemiol. Microbiol., 1980, 8, 82.
56. Cihàk, R.; Vontorkovà, M. Mutat. Res., 1985, 144, 81.
57. Nunoshiba, T.; Nishioka, H. Mutat. Res., 1989, 217, 203.
58. Yoshimura, H. Toxicol. Lett., 2002, 129, 115.
59. Das, N.K. Am. J. Vet. Res., 1984, 45, 252.
60. Swartz, M.N. N. Engl. J. Med., 1997, 337, 491.
61. D'Aoust, J.; Sewell, A.M.; Daley, E.; Greco, P. J. Food Prot., 1992, 55, 428.
62. Tenover, F.C.; Hughes, J.M. J. Am. Vet. Med. Assoc., 1996, 275, 300.
63. Mortensen, J.E.; Nanavaty, J.; Veenhuizen, M.E.; Shryock, T.R. Vet. Med., 1996, 5, 473.
64. Prescott, J.F.; Baggot, J.D. Antimicrobial therapy in veterinary medicine, Prescott-Baggot, Ed.; Iowa State University Press, Ames, 1993.
65. Gellin, G.; Lamglois, B.E.; Dawson, K.A.; Aaron, D.K. Appl. Environ. Microbiol. 1989, 55, 2287.
66. Edrington, T.S.; Harvey, R.B.; Farrington, L.A.; Nisbet, D.J. J. of Food Protection, 2001, 64, 2067.
67. Dunlop, R.H.; McEwen, S.A.; Meek, A.H.; Clarke, R.C.; Black, W.D.; Friendship, R.M. Prev. Vet. Med., 1998, 34, 283.
68. Spanoghe, P.; Pohl, P. Ann. Rech. Vet. 1987, 18, 249.
69. Mathew, A.G.; Upchurch, W.G.; Chattin, S.E. J. Anim. Sci., 1998, 76, 429.
70. Kitai, K.; Kashiwazaki, M.; Adachi, Y.; Kunugita, K.; Arakawa, A. Antimicrob. Agents Chemother., 1987, 31, 1935.
71. Harris, D.L.; Glock, R.D.; Christensen, C.R.; Kinyon, J.M. Vet. Med. Small Anim. Clin. 1972, 67, 61.
72. Taylor, D.J.; Alexander, T.J.L. Br. Vet. J., 1970, 127, 58.
73. Kitai, K.; Kashiwazaki, M.; Adachi, Y.; Kume, T.; Arakawa, A. Antimicrob. Agents Chemother., 1979, 15, 392.
74. Molnàr, L.; Szent-Ivànyi, T. Acta Vet. Acad. Sci. Hung., 1981, 29, 111.
75. Williams, B.J.; Babcock, W.E. Vet. Med. Small Anim. Clin., 1976, 71, 957.
76. Williams, B.J.; Shively, J.E. Vet. Med. Small Anim. Clin., 1978, 73, 349.
77. Wiedling, M. Acta Path. Microbiol. Scand., 1945, 22, 370.
78. Frisk, A.R. Acta. Med. Scand., 1946, 125, 487.
79. Iland, C.N. Nature, 1948, 161, 1010.
80. Coulthard, C.E.; Hale, L.J. Br. J. Pharmacol., 1955, 10, 394.
81. Hennessy, T.D.; Edwards, J.R. Vet. Rec., 1972, 90, 187.
82. Bertschinger, H.U. Arch. Tierheilkd, 1976, 118, 397.
83. English, A.R.; Dunegan, C.M. Proc. Soc. Exp. Biol. Med., 1970, 133, 398.
84. Gund, P.H.; Berkelhammer, G. J. Med. Chem., 1971, 14, 992.
85. Kim, H.K., (Richardson-Merrell), 1972, U.S. Patent 3,644,363.
86. Francis, J.; Lanquist, J.K.; Levi, A.A.; Silk, J.A.; Thorp, J.M. Biochem. J., 1956, 63, 455.
87. Edwards, M.L.; Bambury, R.E.; Ritter, H.W. J. Med. Chem., 1975, 18, 637.
88. Bambury, R.E.; Lutz, C.M.; Miller, L.F.; Kim, H.K.; Ritter, H.W. J. Med. Chem., 1973, 16, 566.
89. Kim, H.K.; Miller, L.F.; Bambury, R.E.; Ritter, H.W. J. Med. Chem., 1977, 20, 557.
90. Dirlam, J.P.; Presslitz, J.E. J. Med. Chem., 1978, 21, 483.
91. Usai, D.; Sanna, P.; Sechi, L.A.; Carta, A., Paglietti, G.; Zanetti, S. L'Igiene Moderna, 2004, 121, 289.
92. Sainz, Y.; Montoya, M.E.; Martinez-Crespo, F.J.; Ortega, M.A.; Lopez de Cerain, A.; Monge A. Arzeim -Forsch. Drug Res., 1999, 49, 55.
93. Ortega, M.A.; Sainz, Y.; Montoya, M.E.; Lopez de Cerain, A.; Monge A. Pharmazie, 1999, 54, 24.
94. Montoya, M.E.; Sainz, Y.; Ortega, M.A.; Lopez de Cerain, A.; Monge A. Farmaco, 1998, 53, 570.
95. Ortega, M.A.; Montoya, M.E.; Jaso, A.; Zarranz, B.; Tirapu, I.; Aldana, I.; Monge A. Pharmazie, 2001, 56, 205.
96. Ortega, M.A.; Sainz, Y.; Montoya, M.E.; Jaso, A.; Zarranz, B.; Aldana, I.; Monge A. Arzeim. -Forsch. Drug Res., 2002, 52, 113.
97. Zarranz, B.; Jaso, A.; Aldana, I. Monge A. Bioorg. Med. Chem., 2003, 11, 2149.
98. Jaso, A.; Zarranz, B.; Aldana, I.; Monge A. Eur. J. Med. Chem., 2003, 38, 791.
99. a) Rahabar Nikookar, M.E.; Sanna, P.; Carta, A.; Paglietti, G.; Sechi, L.; Fiori, P.L.; Zanetti, S. XVIth International Symposium on Medicinal Chemistry, Bologna-Italy, 18-22 September 2000. pc-123.
100. b) Carta, A.; Paglietti, G.; Rahabar Nikookar, M.E.; Sanna, P.; Sechi, L.; Zanetti, S. Eur. J. Med. Chem., 2002, 37, 355.
101. Carta, A.; Loriga, M.; Paglietti, G.; Mattana, A.; Fiori, P.L.; Mollicotti, P.; Sechi, L.; Zanetti, S. Eur. J. Med. Chem., 2004, 39, 195.
102. Zanetti, S.; Sechi, L.; Mollicotti, P.; Cannas, S.; Bua, A.; Deriu, A.; Carta, A.; Paglietti, G. Int. J. Antimicrob. Agents, 2005, 25, 177.
103. Haley, T.J.; Flesher, A.M.; Veomett, R.; Vincent, J. Proc. Soc. Exp. Biol. Med., 1957, 96, 579.
104. Haley, T.J.; Flesher, A.M.; Komesu, N. Nature, 1959, 184, 198.
105. Brown, J.M. Cancer Res., 1999, 59, 5863.
106. Monge A.; Palop, J.A.; Lopez de Cerain, A.; Senador, V.; Martinez-Crespo, F.J.; Sainz, Y.; Narro, S.; Garcìa, E.; de Miguel, C.; Gonzales, M.; Hamilton, E.; Barker, A.J.; Clarke, E.D.; Greenhow, D.T. J. Med. Chem., 1995, 38, 1786.
107. Monge A.; Martinez-Crespo, F.J.; Lopez de Cerain, A.; Palop, J.A.; Narro, S.; Senador, V.; Martìn, A.; Sainz, Y.; Gonzales, M.; Hamilton, E.; Barker, A.J. J. Med. Chem., 1995, 38, 4488.
108. Ortega, M.A.; Morancho, M.J.; Martinez-Crespo, F.J.; Sainz, Y.; Montoya, M.E.; Lopez de Cerain, A.; Monge A. Eur. J. Med. Chem., 2000, 35, 21.
109. Ganley, B.; Chowdhury, G.; Bhansali, J.; Daniels, J.S.; Gates, K.S. Bioorg. Med. Chem., 2001, 9, 2395.
110. Gali-Muhtasib, H.U.; Haddadin, M.J.; Rahal, D.N.; Younes, I.H. Oncol. Rep., 2001, 8, 679.
111. Naylor, M.A.; Nolan, J.; Sutton, B.; Tocher, J.H.; Fielden, E.M.; Adams, G.E.; Stratford, I.J. Anticancer Drug Design, 1993, 8, 439.
112. Diab-Assef, M.; Haddadin, M.J.; Yared, P.; Assaad, C.; Gali-Muhtasib, H.U. Mol. Carcinog., 2002, 33, 198.
113. Carmeliet, P.; Dor, Y.; Herbert, J.M.; Fukumura, D.; Brusselmans, K.; Dewerchin, M.; Neeman, M.; Bono, F.; Abramovitch, R.; Maxwell, P.; Koch, C.J.; Ratcliffe, P.; Moons, L.; Jain, R.K.; Collen, D.; Keshert, E. Nature, 1998, 394, 485.
114. Gali-Muhtasib, H.U.; Sidani, M.; Geara, F.; Diab-Assef, M.; Al-Hmaira, J.; Haddadin, M.J.; Zaatari, G. Int. J. Oncol., 2004, 24, 1121.
115. Harakeh, S.; Diab-Assef, M.; El-Sabban, M.; Haddadin, M.J.; Gali-Muhtasib, H.U. Chem. Biol. Interact., 2004, 148, 101.
116. Haddadin M.J.; Issidorides, C.H. Heterocycles, 1993, 35, 1503.
117. Gali-Muhtasib, H.U.; Haddadin, J.M.; Nazer, Z.M.; Sodir, N.M.; Maalouf, S.W. Medical Oncology, 1998, 15, 262.
118. Aguirre, G.; Cerecetto, H.; Di Maio, R.; Gonzàlez, M.; Montoya Alfaro, M.E.; Jaso, A.; Zarranz, B.; Ortega, M.A.; Aldana, I.; Monge-Vega, A. Bioorg. Med. Chem. Lett., 2004, 14, 3835.
119. Glazer, E.A.; Chappel, L.R. J. Med. Chem., 1982, 25, 766.
120. Loriga, M.; Nuvole, A.; Paglietti, G.; Fadda, G.; Zanetti, S. Eur. J. Med. Chem., 1990, 25, 527.
121. Katritzy, A.R.; Lagowski, J.M. In Chemistry of the Heterocyclic N-oxides, Academic Press Inc: New York, 1971, p. 21.
122. Ochiai, E. In Aromatic Amine Oxides, Elsevier Publishing Co.: Amsterdam, 1967, pp. 19-51.
123. Haddadin, M.J.; Issidorides, C.H. Tetrahedron Lett., 1965, 3253.
124. Haddadin, M.J.; Issidorides, C.H. J. Org. Chem., 1966, 4067.
125. Ley, K.; Seng, F. Synthesis, 1975, 415.
126. Haddadin, M.J.; Issidorides, C.H. Heterocycles, 1976, 4, 767.
127. Gasco, A.; Boulton, A. In Advances in Heterocyclic Chemistry, Katritzky-Boulton, Ed.; Academic Press Inc., New York, 1981, Vol. 29, pp. 252-339.
128. Brown, D.J. In The Heterocycles Compounds: The Quinoxalines Supplement II; Taylor-Wipf, Ed.; John Wiley & Sons, Inc: Hoboken, 2004.
129. Cheeseman, G.W.H.; Cookson, R.F. In The Heterocycles Compounds: Condensed Pyrazines; Weissberger-Taylor, Ed.; John Wiley & Sons, Inc: New York, 1979.
130. Cheeseman, G.W.H.; Werstiuk, E.S.G. In Advances in Heterocyclic Chemistry: Quinoxaline Chemistry: Developments 1963-1975, Katritzky-Boulton, Ed.; Academic Press Inc., New York, 1978, Vol. 22, pp. 368-429.
131. Tanaka, A.; Usui, T. Chem. Pharm. Bull., 1981, 29, 110.
132. Birkofer, L.; Quittman, W. Chem. Ber., 1986, 119, 257.
133. Heyns, K.; Behse, E.; Franke, W. Chem. Ber., 1981, 114, 240.
134. Dirlam, J.P.; McFarland, J. W. J. Org. Chem., 1977, 42, 1360.
135. Glazer, E.A.; Presslitz, J.E. J. Med. Chem., 1982, 25, 868.
136. Stumm, G.; Niclas, H.J. J. Prakt. Chem., 1989, 331, 736.
137. Borah, H.N; Boruah, R.C.; Sandhu, J.S. Heterocycles, 1984, 22, 2323.
138. Mufarrij, N.A.; Haddadin, M.J.; Issidorides, C.H.; McFarland, J.W.; Johnston, J.D. J. Chem. Soc. Perkin I, 1972, 965.
139. Devi, P.; Sandhu, J.S.; Thyagarajan, G. J.C.S. Chem. Comm., 1979, 710.
140. Borah, H.N; Devi, P.; Sandhu, J.S.; Baruah, J.N. Tetrahedron, 1984, 40, 1617.
141. Monge, A.; Llamas, A.; Pascual, M.A. An. Quim., 1977, 73, 912;
142. Monge, A.; Llamas, A.; Pascual, M.A. Chem. Abstr., 1977, 87, 184460.
143. Li, J.; Ji, M.; Hua, W.; Hu, H. Indian J Chem. (B), 2001, 40, 1230.
144. Monge, A.; Llamas, A.; Pasqual, M.A. An. Quim., 1977, 73, 1208;
145. Monge, A.; Llamas, A.; Pasqual, M.A. Chem. Abstr., 1978, 89, 146871.
146. Jarrar, A.A.; Fataftah, Z.A. Tetrahedron, 1977, 33, 2127.
147. Monge, A.; Palop, J.A.; González, M.; Martinez-Crespo, F.J.; López de Ceráin, A.; Sáinz, Y.; Narro, S.; Barker, A.J.; Hamilton, E. J. Heterocycl. Chem., 1995, 32, 1213.
148. Abushanab, E. J. Org. Chem., 1973, 38, 3105.
149. Hasegawa, M.; Takabakate, T. Synthesis, 1985, 938.
150. Takabakate, T.; Hasegawa, M. J. Heterocycl. Chem., 1987, 24, 529.
151. Chupakhin, O.N.; Kotvskaya, S.K.; Perova, N.M.; Baskakova, Z.M.; Charushin, V.N. Khim. Geterotsikl. Soedin., 1999, 35, 520.
152. Monge, A.V.; Gil, M.J.; Basilio, A.; Giraldez, A.; Fernández-Alvarez, E. Eur. J. Med. Chem., 1986, 21, 251.
153. Monge, A. V.; Gil, M.J.; Fernández-Alvarez, E. J. Heterocyclic Chem., 1984, 21, 1271.
154. Chupakhim, O.N.; Kotvskaya, S.K.; Perova, N.M.; Baskakova, Z.M.; Charushim, V.N. Khim. Geterotsikl. Soedim., 1999, 35, 520.
155. Kotovskaya, S.K.; Perova, N.M.; Charushin, V.N.; Chupakhin, O.N. Mendeleev Commun., 1999, 76.
156. Monge, A.; Palon, J.A.; Piñol, A.; Martinez-Crespo, F.J.; Narro, S.; González, M.; Sáinz, Y.; López de Ceráin, A.; Hamilton, E.; Barker, A.J. J. Heterocycl. Chem., 1994, 31, 1135.
157. Monge, A.; Palop, J.A.; Del Castillo, J.C.; Calderò, J.M.; Roca, J.; Romero, G.; Del Rio, J.; Lasheras, B. J. Med. Chem., 1993, 36, 2745.
158. Martinez-Crespo, F.J.; Palop, J.A.; Sainz, Y.; Narro, S.; Senador, V.; González, M.; López de Ceráin, A.; Monge, A.; Hamilton, E.; Barker, A.J. J. Heterocycl. Chem., 1996, 33, 1671.
159. Hahn, W.E.; Kedzierska, Z.; Muszkiet, B. Lodz. Tow. Nauk. Pr Wydz. 3 Acta Chim., 1970, 15, 77;
160. Hahn, W.E.; Kedzierska, Z.; Muszkiet, B. Chem. Abstr., 1971, 75, 98536.
161. Elina, A.S.; Tsyrulnikova, L.G., Zh. Obshch. Khim., 1963, 33, 1544;
162. Elina, A.S.; Tsyrulnikova, L.G., Chem. Abstr., 1963, 59, 12807.
163. Figdor, S.K.; Hobbs, D.C. Can. J. Chem.; 1982, 60, 2797.
164. Mahejanshetti, C.S.; Balse, M.N. Indian J. Chem., Sect. B, 1978, 16, 830.
165. Abushanab, E. J. Org. Chem., 1970, 35, 4279.
166. Pfizer Inc., Brit. Pat. 1,271,194; Chem.Abstr., 1972, 77, 34575w.
167. Horn, G.; Schulze, W.; Tresselt, D. J. Prakt. Chem., 1985, 327, 156.
168. Nazer, M.Z.; Haddadin, M.; Petridou, J.P.; Issidorides, C.H. Heterocycles, 1977, 6, 541.
169. Heyns, K.; Behse, E.; Franke, W. Chem. Ber., 1981, 114, 246.
170. Hahn, W.E.; Lesiak, J. Pol. J. Chem., 1985, 59, 627;
171. Hahn, W.E.; Lesiak, J. Chem. Abstr., 1987, 106, 84552.
172. Demirdji, S.H.; Haddadin, M.J.; Issidorides, C.H. J. Heterocycl. Chem., 1983, 20, 1735.
173. Homaidan, F.R.; Issidorides, C.H. Heterocycles, 1981, 16, 411.
174. Novácek, L.; Nechvátal, M. Collect. Czech. Chem. Commun., 1988, 53, 1302.
175. Novácek, L.; Seménková, L.; Holik, M.; Soska, J. Cesk. Farm., 1986, 35, 145;
176. Novácek, L.; Seménková, L.; Holik, M.; Soska, J. Chem. Abstr., 1986, 105, 749.
177. Jarrar, A.A. J. Heterocycl. Chem., 1978, 15, 177.
178. Atfah, A.; Hill, J. J. Chem. Soc., Perkin Trans. I, 1989, 221.
179. Haddain, M.J.; Atfah, M.A. J. Org. Chem., 1982, 47, 1772.
180. Hirota, T.; Namba, T.; Sasaki, K. J. Heterocyclic. Chem., 1987, 24, 949.
181. Haddadin, M.J.; Samaha, M.S.; Hajj-Ubayd, A.B. Hetercycles, 1992, 33, 541.
182. Haddadin, M.J.; Atfah, M.A. Heterocycles, 1981, 16, 251.
183. Musatova, I.S.; Pol'shakov, V.I.; Dvoryantseva, G.G.; Chistyakov, V.V.; Elina, A.S. Chim.-Farm. Zh., 1986, 20, 182;
184. Musatova, I.S.; Pol'shakov, V.I.; Dvoryantseva, G.G.; Chistyakov, V.V.; Elina, A.S. Chem. Abstr., 1987, 106, 32985y.
185. Dirlam, J.P.; Czuba, L.J.; Dominy, B.W.Jr.; James, R.B.; Pezzullo, R.M.; Presslitz, J.P.; Windisch, W.W. J. Med. Chem., 1979, 22, 118.
186. Monge, A.; Palop, J.A.; Urbasos, I. J. Heterocycl. Chem., 1989, 26, 1623.
187. Dirlam, J.P.; Cue, B.W.; Gombatz, K.J. J. Org. Chem., 1978, 43, 76.
188. Usta, J.A.; Haddadin, M.J.; Issidorides, C.H.; Jarrar, A.A. J. Heterocyclic Chem., 1981, 18, 655.
189. Günther, H.; Gronenborn, A. Heterocycles, 1978, 11, 337.
190. Sabri, S.S.;El-Abadelah, M.M.; Al-Bitar, B.A. Heterocycles, 1987, 26, 699.
191. Acree, W.E.; Powell, J.R.; Tucker, S.A.; Ribeiro da Silva, M.D.M.C.; Matos, M.A.R.; Gonçalves, J.M.; Santos, L.M.N.B.F.; Morais, V.M.F.; Pilcher, G. J. Org. Chem., 1977, 42, 3722 and 8960 (erratum).
192. Hara, H.; van der Plas, H.C. J. Heterocycl. Chem., 1982, 19, 1285.
193. Ryan, M.D.; Scamehorn, R.G.; Kovacic, P. J. Pharm. Sci., 1985, 74, 492.
194. Crawford, P.W.; Scamehorn, R.G.; Hollstein, U.; Ryan, M.D.; Kovacic, P. Chem. Biol. Interact., 1986, 60, 67.
195. McDonald, L.; Arora, S.K. Acta Crystallogr., Sect. B, 1981, 37, 1445.
196. Cong, Q.; Lin, S.; Wang, H. Jiegou Huaxue, 1989, 8, 31;
197. Cong, Q.; Lin, S.; Wang, H. Chem. Abstr., 1989, 111, 68380.
198. Sakata, G.; Makijo, K.; Morimoto, K. Heterocycles, 1985, 23, 143.
199. Kawata, H.; Kikuchi, K.; Kokubun, H. J. Photochem., 1983, 21, 343.
200. Haddadin, M.J.; Issidorides, C.H. Tetrahedron Lett., 1967, 753.
201. Haddadin, M.J.; Agopian, G.; Issidorides, C.H. J. Org. Chem., 1971, 36, 514.
202. Ames, J.R.; Hollstein, U.; Gagneux, A.R.; Ryan, M.D.; Kovacic, P. Free Radical Biology and Medicine, 1987, 3, 85.