Pyrazolo[1,5-α][1,3,5]triazines (5-Aza-9-deazapurines): Synthesis and biological activity

Heterocycles

Volumn 75, Issue 7, 2008, Pages 1575-1622

  Dolzhenko, Anton V ^a   Dolzhenko, Anna V ^a   Chui, Wai Keung ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Fused Pyrazole; Fused s Triazine; Purine Isostere; Pyrazolo 1,5, triazine; Ring Closure

Indexed keywords

EID: 51349150681     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-08-629     Document Type: Article

References (153)

1. Part 2 in the series of reviews "Fused 1,3,5-triazines." For Part 1 see:. Dolzhenko A.V., Dolzhenko A.V., and Chui W.K. Heterocycles 68 (2006) 1723
2. Checchi S., and Ridi M. Gazz. Chim. Ital. 87 (1957) 597
3. Vishwakarma J.N., Mofizuddin M., Ila H., and Junjappa H. J. Heterocycl. Chem. 25 (1988) 1387
4. Dutta M.C., Chanda K., Helissey P., and Vishwakarma J.N. J. Heterocycl. Chem. 42 (2005) 975
5. Graubaum H., and Schweim H.G. Arch. Pharm. (Weinheim) 324 (1991) 257
6. For reviews on 3(5)-aminopyrazoles see:. Elnagdi M.H., Abdel-Galil F.M., Riad B.Y., and Elgemeie G.E.H. Heterocycles 20 (1983) 2437
7. Giuseppe D., Salvatore P., and Demetrio R. Trends Heterocycl. Chem. 2 (1991) 97
8. Elmaati T.M.A., and El-Taweel F.M. J. Heterocycl. Chem. 41 (2004) 109
9. For reviews on imidates see:. Neilson D.G. In: Patai S., and Rappoport Z. (Eds). 'Chemistry of Amidines and Imidates: Imidates Including Cyclic Imidates,' 2 (1991), Wiley, Chichester 425-483
10. Nakajima N., and Ubukata M. In: Charette A. (Ed). Science of Synthesis: Imidates 22 (2005), Georg Thieme Verlag, Stuttgart 343-360
11. Nakajima N., and Ubukata M. In: Charette A. (Ed). 'Science of Synthesis: Thioimidates and Their Derivatives,' 22 (2005), Georg Thieme Verlag, Stuttgart 361-366
12. Bekircan O., Kuxuk M., Kahveci B., and Kolayli S. Arch. Pharm. (Weinheim) 338 (2005) 365
13. Kaddachi M.T., Hajjem B., and Baccar B. J. Soc. Chim. Tunisie 2 (1988) 17
14. Gilligan P.J., Folmer B.K., Hartz R.A., Koch S., Nanda K.K., Andreuski S., Fitzgerald L., Miller K., and Marshall W.J. Bioorg. Med. Chem. 11 (2003) 4093
15. Strohmeyer T.W., Sliskovic D.R., Lang S.A., and Lin Y. J Heterocycl. Chem. 22 (1985) 7
16. Demidchuk B.A., Brovarets V.S., Chernega A.N., Howard J.A.K., Vasilenko A.N., Turov A.V., and Drach B.S. Russ. J. Gen. Chem. 77 (2007) 474
17. Karanik M., Paetzel M., and Liebscher J. Synthesis (2003) 1201
18. Briel D. Pharmazie 50 (1995) 675
19. Tam S.Y.K., Hwang J.S., De las Heras F.G., Klein R.S., and Fox J.J. J Heterocycl. Chem. 13 (1976) 1305
20. Lee C.S., Du J., and Chu C.K. Nucleosides Nucleotides 15 (1996) 1223
21. Xiang Y., Du J., and Chu C.K. Nucleosides Nucleotides 15 (1996) 1821
22. Liang C., Ma T., Cooperwood J.S., Du J., and Chu C.K. Carbohydr. Res. 303 (1997) 33
23. Ullas G.V., Chu C.K., Ahn M.K., and Kosugi Y. J. Org. Chem. 53 (1988) 2413
24. Koren B., Kovac F., Petric A., Stanovnik B., and Tisler M. Tetrahedron 32 (1976) 493
25. Boes M., Riemer C., and Stadler H. Pat. EP 941994, 1999. Chem. Abstr. 131 (1999) 214-304
26. Insuasty H., Estrada M., Cortes E., Quiroga J., Insuasty B., Abonia R., Nogueras M., and Cobo J. Tetrahedron Lett. 47 (2006) 5441
27. Insuasty H., Estrada M., Cobo J., Low J.N., and Glidewell C. Acta Crystallogr. C62 (2006) 122
28. Cohen C. Pat. DE 2900288, 1979. Chem. Abstr. 91 (1979) 157770
29. Zahran M.A., Hassanien A.A., Emam H.A., El-Said M.Z., and Ammar Y.A. Croat. Chem. Acta 70 (1997) 1039
30. Ammar Y.A., Saleh N.M., Micky J.A., Abbas H.A.S., and El-Gaby M.S.A. Indian J. Chem. 43B (2004) 2203
31. Saleh N.M., Ammar Y.A., Micky J.A., Abbas H.A.S., and El-Gaby M.S.A. Indian J. Chem. 43B (2004) 2195
32. Tam S.Y.K., Klein R.S., Wempen I., and Fox J.J. J. Org. Chem. 44 (1979) 4547
33. Abbas-Temirek H.H. Assiut Univ. J. Chem. 35 (2006) 37
34. Ried W., and Aboul-Fetouh S. Tetrahedron 44 (1988) 7155
35. Lubbers T., Angehrn P., Gmunder H., Herzig S., and Kulhanek J. Bioorg. Med. Chem. Lett. 10 (2000) 821
36. Elgemeie G.H., El-Ezbawy S.R., and El-Aziz H.A. Synth. Commun. 31 (2001) 3453
37. Elgemeie G.H., and Sood S.A. J. Chem. Res. S (2001) 439
38. Elgemeie G.H., Zahran M.K., and Abbas E.M. Pigm. Resin Technol. 31 (2002) 297
39. Alqaradawi S.Y., and Elgemeie G.H. Synth. Commun. 34 (2004) 805
40. Caulkett P.W.R., Jones G., Collis M.G., and Poucher S.M. Pat. EP 459702, 1991. Chem. Abstr. 117 (1992) 171476
41. Mayer K.H., Sasse K., and Koenig A.V. Pat. DE 3001498, 1981. Chem. Abstr. 95 (1981) 132967
42. Elgemeie G.H., El-Ezbawy S.R., and Ali H.A. Synth. Commun. 31 (2001) 3459
43. Gupta C.M., Jones G.H., and Moffatt J.G. J. Org. Chem. 41 (1976) 3000
44. Cartwright D., Urlwin-Smith P., and Collins D.J. Pat. EP 4171, 1979. Chem. Abstr. 92 (1980) 94442
45. Salem M.A.I., Madkour H.M.F., Al-Nuaimi I.S., and Al-Qaradawi S.Y. J. Serb. Chem. Soc. 58 (1993) 89
46. Fischer E., Kreutzmann J., Rembarz G., and Rosenthal S. Pharmazie 31 (1976) 546
47. Fischer E., Rosenthal S., and Kreutzmann J. Pat. DD 123468, 1976. Chem. Abstr. 87 (1977) 102386
48. Krueger M., Westermann J., Arndt F., Rees R., and Hunt R.G. Pat. EP 297490, 1989. Chem. Abstr. 111 (1989) 7438
49. Chu C.K. Heterocycles 22 (1984) 345
50. Rooney C.S., and Williams H.W.R. Pat. US 3995039, 1976. Chem. Abstr. 86 (1977) 106664
51. Vogel A., and Troxler F. Pat. DE 2424334, 1974. Chem. Abstr. 83 (1975) 10160
52. Kobe J., O'Brien D.E., Robins R.K., and Novinson T. J. Heterocycl. Chem. 11 (1974) 991
53. Novinson T., Senga K., Kobe J., Robins R.K., O'Brien D.E., and Albert A.A. J. Heterocycl. Chem. 11 (1974) 691
54. Vogel A., and Troxler F. Helv. Chim. Acta 58 (1975) 761
55. Peseke K. Pat. DD 92457, 1972. Chem. Abstr. 78 (1973) 111376
56. Peseke K. Pharmazie 30 (1975) 802
57. Yamada Y., Yasuda H., and Yoshizawa K. Heterocycles 48 (1998) 2095
58. Chu C.K., Watanabe K.A., and Fox J.J. J. Heterocycl. Chem. 17 (1980) 1435
59. Robins R.K., Revankar G.R., O'Brien D.E., Springer R.H., Novinson T., Albert A., Senga K., Miller J.P., and Streeter D.G. J. Heterocycl. Chem. 22 (1985) 601
60. Fujii S., Kawamura H., Kiyokawa H., and Yamada S. Pat. EP 269859, 1988. Chem. Abstr. 109 (1988) 211092
61. O'Brien D.E., Senga K., and Novinson T. Pat. US 3910907, 1975. Chem. Abstr. 84 (1971) 44171
62. Kobe J., O'Brien D.E., and Robins R.K. Pat. US 3865824, 1975. Chem. Abstr. 83 (1971) 10163
63. Kiyokawa H., Yamada S., Miyajima K., Edamatsu K., Tatsumi K., Yamauchi T., Kishi K., and Kiyono K. Pat. EP 594149, 1994. Chem. Abstr. 122 (1995) 81414
64. Venkatesan A.M. Pat. US 5358947, 1994. Chem. Abstr. 122 (1995) 81413
65. Bernard P., and Raboisson P. Pat. FR 2842809, 2004. Chem. Abstr. 140 (2004) 146171
66. Gilligan P.J., Rabel R.S.R., and Meenan P.A. Pat. US 2005113375, 2005. Chem. Abstr. 143 (2005) 7737
67. Senga K., Kobe J., Robins R.K., and O'Brien D.E. J. Heterocycl. Chem. 12 (1975) 893
68. Vicentini C.B., Mares D., Tartari A., Manfrini M., and Forlani G. J. Agric. Food Chem. 52 (2004) 1898
69. Mares D., Romagnoli C., Andreotti E., Forlani G., Guccione S., and Vicentini C.B. Mycol. Res. 110 (2006) 686
70. Kristen H., Goerges S., and Peseke K. Pat. DD 203546, 1983. Chem. Abstr. 100 (1984) 156642
71. Chu C.K. J. Heterocycl. Chem. 21 (1984) 389
72. EI-Dean A.M.K., and Geies A. J. Chem. Res. S (1997) 352
73. EI-Dean A.M.K., and Geies A. J. Chem. Res. (M) S (1997) 2255
74. El-Gaby M.S., Taha N.M., Micky J.A., and El-Sharief M.A.M.Sh. Acta Chim. Sloven. 49 (2002) 159
75. Novinson T., Bhooshan B., Okabe T., Revankar G.R., Robins R.K., Senga K., and Wilson H.R. J. Med. Chem. 19 (1976) 512
76. Olson R.E., and Frietze W.E. Pat. WO 9967247, 1999. Chem. Abstr. 132 (2000) 64274
77. Lalezari I., and Sadeghi-Milani S. J. Heterocycl. Chem. 15 (1978) 171
78. Senga K., Robins R., and O'Brien D.E. J. Heterocycl. Chem. 12 (1975) 899
79. Lalezari I. J. Heterocycl. Chem. 13 (1976) 1249
80. Albert A.H., Robins R.K., and O'Brien D.E. J. Heterocycl. Chem. 10 (1973) 885
81. El Khadem H.S., Foltz R.L., Novinson T., and Senga K. J. Heterocycl. Chem. 12 (1975) 1255
82. Senga K., O'Brien D.E., Scholten M.B., Novinson T., Miller J.P., and Robins R.K. J. Med. Chem. 25 (1982) 243
83. Almansa C., de Arriba A.F., Cavalcanti F.L., Gomez L.A., Miralles A., Merlos M., Garcia-Rafanell J., and Forn J. J. Med. Chem. 44 (2001) 350
84. Gilligan P., Chorvat R., and Arvanitis A.G. Pat. US 6060478, 2000. Chem. Abstr. 132 (2000) 321873
85. He L., Gilligan P.J., Zaczek R., Fitzgerald L.W., McElroy J., Shen H.S.L., Saye J.A., Kalin N.H., Shelton S., Christ D., Trainor G., and Hartig P. J. Med. Chem. 43 (2000) 449
86. Darrow J.W., De Lombaert S., Blum C., Tran J., Giangiordano M., Griffith D.A., and Carpino P.A. Pat. WO 2001023387, 2001. Chem. Abstr. 134 (2001) 280866
87. Darrow J.W., De Lombaert S., Blum C., Tran J., Giangiordano M., Griffith D.A., and Carpino P.A. Pat. WO 2001023388, 2001. Chem. Abstr. (2001) 134 280853
88. Gilligan P.J. Pat. WO 2002072202, 2002. Chem. Abstr. 137 (2002) 237769
89. Jagoda E., Contoreggi C., Lee M.J., Kao C.H.K., Szajek L.P., Listwak S., Gold P., Chrousos G., Greiner E., Kim B.M., Jacobson A.E., Rice K.C., and Eckelman W. J. Med. Chem. 46 (2003) 3559
90. Raboisson P., Schultz D., Muller C., Reimund J., Pinna G., Mathieu R., Bernard P., Do Q.T., DesJarlais R.L., Justiano H., Lugnier C., and Bourguignon J.J. Eur. J. Med. Chem. (2008) doi: 10.1016/j.ejmech.2007.05.016
91. Griffith D.A. Pat. US 2004157839, 2004. Chem. Abstr. 141 (2004) 190806
92. Griffith D.A. Pat. WO 2005049615, 2005. Chem. Abstr. 143 (2005) 26645
93. Ghosh A., and Wei L. Pat. WO 2006131807, 2006. Chem. Abstr. (2007) 146 62749
94. Su Y.D., Zheng Y.H., and Li Y.C. Hecheng Huaxue 14 (2006) 380
95. Kobe J., Robins R.K., and O'Brien D.E. J. Heterocycl. Chem. 11 (1974) 199
96. Kobe J., Springer R.H., and O'Brien D.E. Pat. US 3846423, 1974. Chem. Abstr. 82 (1975) 43472
97. Mohareb R.M., Zohdi H.F., and Wardakhan W.W. Monatsh. Chem. 126 (1995) 1391
98. Ibrahim M.K.A., Elghandour A.H.H., Elshikh S.M.M., and Mishael S.A. Indian J. Chem. 36B (1997) 91
99. Ghabrial S.S., Zaki M.Y., and Eldin S.M. Egypt. J. Pharm. Sci. 37 (1996) 329
100. El-Hawash S.A., and El-Mallah A.I. Pharmazie 53 (1998) 368
101. Nie Z., Perretta C., Erickson P., Margosiak S., Almassy R., Lu J., Averill A., Yager K.M., and Chu S. Bioorg. Med. Chem. Lett. 17 (2007) 4191
102. Capuano L., and Schrepfer H.J. Chem. Ber. 104 (1971) 3039
103. Ramiz M.M.M., Elghandour A.H.H., Ibrahim M.K.A., and Mansour O.A.E.R. Arch. Pharm. (Weinheim) 322 (1989) 557
104. Elnagdi M.H., E.M. E.M., Kandeel Z., and Fahmy S.M. Z. Naturforsch, B. 32B (1977) 430
105. Youssef M.M., and Al-Haiza M.A. Egypt. J. Chem. 43 (2000) 165
106. Nie Z., Perretta C., Erickson P., Margosiak S., Lu J., Averill A., Almassy R., and Chu S. Bioorg. Med. Chem. Lett. 18 (2008) 619
107. De Las Heras F.G., Chu C.K., Tam S.Y.K., Klein R.S., Watanabe K.A., and Fox J.J. J. Heterocycl. Chem. 13 (1976) 175
108. Cabon G., Gaucher B., Gegout A., Heulle S., and Masquelin T. Chimia 57 (2003) 248
109. Guzi T.J., and Paruch K. Pat. US 2005187219, 2005. Chem. Abstr. 143 (2005) 248417
110. El-Dean A.M.K., Atalla A.A., and Gaber A.M. Bull. Fac. Sci. Assiut Univ. 19 (1990) 23
111. Mackenzie S.M., and Stevens M.F.G. J Chem. Soc. C (1970) 2298
112. Gescher A., Stevens M.F.G., and Turnbull C.P. J. Chem. Soc., Perkin Trans. 1 (1977) 103
113. Stevens M.F.G., Bliss E.A., Brown T.B., and Mackenzie S.M. Eur. J. Med. Chem. 19 (1984) 375
114. Elmoghayar M.R.H., Ghali E.A., Ramiz M.M.M., and Elnagdi M.H. Liebigs Ann. Chem. (1985) 1962
115. Elmoghayar M.R.H., Abdalla S.O., Yousry M., and Nasr A.S. J. Heterocycl. Chem. 21 (1984) 781
116. Abed N.M., Elagamey A.G.A., and Harb A.F.A. J. Chem. Soc. Pak. 10 (1988) 151
117. Abed N.M., Elagamey A.G.A., Sowellim S.Z., and Harb A.F.A. Rev. Roum. Chim. 33 (1988) 393
118. Chu C.K., and Suh J. Nucleic Acid Chem. 4 (1991) 19
119. Chu C.K., Suh J., Mesbah M., and Cutler S.J. J. Heterocycl. Chem. 23 (1986) 349
120. El-Saraf G., El-Sayed A., and El-Saghier M.M. Heteroarom Chem. 14 (2003) 211
121. Sato S., Tatsumi K., and Nishino T. Adv. Exp. Med. Biol. 309A (1991) 135
122. Okamoto K., Iwamoto T., and Nishino T. Flavins and Flavoproteins 1993: New Tight Binding Inhibitors of Xanthine Oxidase (1994), Walter de Gruyter & Co, Berlin 731-734
123. Okamoto K. Yokohama Igaku, 1994, 45, 47. Chem. Abstr. 120 (1994) 292737
124. Okamoto K., and Nishino T. J. Biol. Chem. 270 (1995) 7816
125. Naito S., Nishimura M., and Tamao Y. J. Pharm. Pharmacol. 52 (2000) 173
126. Uematsu T., and Nakashima M. J. Pharmacol. Exp. Ther. 270 (1994) 453
127. Suzuki H., Suematsu M., Ishii H., Kato S., Miki H., Mori M., Ishimura Y., Nishino T., and Tsuchiya M. J. Clin. Invest. 93 (1994) 155
128. Shibukawa A., Kadohara M., He J.Y., Nishimura M., Naito S., and Nakagawa T. J. Chromatogr. A 694 (1995) 81
129. Nishimura M., Yamaoka K., Naito S., and Nakagawa T. Biol. Pharm. Bull. 20 (1997) 1285
130. Naito S., and Nishimura M. Yakugaku Zasshi 121 (2001) 989
131. Naito S., and Nishimura M. Xenobiotica 32 (2002) 491
132. Naito S., and Nishimura M. Biol. Pharm. Bull. 25 (2002) 674
133. Hashimoto K., and Inai M. Pat. EP 414200, 1991. Chem. Abstr. 115 (1991) 29386
134. Matsugi M., Hashimoto K., Inai M., Fukuda N., Furuta T., Minamikawa J., and Otsuka S. Tetrahedron: Asymmetry 6 (1995) 2991
135. Hashimoto K., Matsugi M., Fukuda N., and Kurogi Y. Phosphorus, Sulfur Silicon Relat. Elem. 120-121 (1997) 305
136. Prevost G., Lonchampt M.O., Kim S., Morgan B., Ulibarri G., and Thurieau C. Pat. WO 2002050079, 2002. Chem. Abstr. 137 (2002) 47234
137. Miller J.P., Sigman C.C., Johnson H.L., Novinson T., Springer R.H., Senga K., O'Brien D.E., and Robins R.K. Adv. Cyclic Nucleotide Protein Phosphor. Res. 16 (1984) 277
138. Sullivan T.A., Duemler B.H., Kuttesch N.J., Keravis T.M., and Wells J.N. J. Cyclic Nucleotide Protein Phosphor. Res. 11 (1986) 355
139. de Zwart M., Vollinga R.C., Beukers M.W., Sleegers D.F., von Frijtag Drabbe Kunzel J.K., De Groote M., and Ijzerman A.P. Drug Dev. Res. 48 (1999) 95
140. Vu C., Petter R.C., and Kumaravel G. Pat. WO 2004092170, 2004. Chem. Abstr. 141 (2004) 395582
141. Raboisson P., Baurand A., Cazenave J.P., Gachet C., Schultz D., Spiess B., and Bourguignon J.J. J. Org. Chem. 67 (2002) 8063
142. Arvanitis A.G., and Chorvat R.J. Pat. WO 9803510, 1998. Chem. Abstr. 128 (1998) 154103
143. He L., Gilligan P., Chorvat R., and Arvanitis A.G. Pat. WO 9938868, 1999. Chem. Abstr. 131 (1999) 144616
144. He L., Gilligan P., Chorvat R., and Arvanitis A.G. Pat. US 6313124, 2001. Chem. Abstr. (2001) 135 344507
145. He L., Gilligan P., Chorvat R., and Arvanitis A.G. Pat. US 6191131, 2001. Chem. Abstr. (2001) 134 178572
146. Li Y.W., Fitzgerald L., Wong H., Lelas S., Zhang G., Lindner M.D., Wallace T., McElroy J., Lodge N.J., Gilligan P., and Zaczek R. CNS Drug Rev. 11 (2005) 21
147. Chen C. Curr. Med. Chem. 13 (2006) 1261
148. Zhao Y., Valdez G.R., Fekete E.M., Rivier J.E., Vale W.W., Rice K.C., Weiss F., and Zorrilla E.P. J. Pharmacol. Exp. Ther. 323 (2007) 846
149. Cao X., Liang L., Hadcock J.R., Iredale P.A., Griffith D.A., Menniti F.S., Factor S., Greenamyre J.T., and Papa S.M. J Pharmacol. Exp. Ther. 323 (2007) 318
150. Junien J.L., Guillaume M., Lakatos C., and Sterne J. Arch. Int. Pharmacodyn. Ther. 252 (1981) 313
151. Guillaume M., and Lakatos C. Prostaglandins Ser. 3 (1983) 332
152. Ruff F., Floch A., Chastagnol D., Blanc M., and Santais M.C. Prostaglandins Ser. 3 (1983) 205
153. Junien J.L., Lakatos C., Brohon J., Guillaume M., and Sterne J. Agents Actions 12 (1982) 459