The synthesis and physiological activity of 2,3,4,5-tetrahydro-1H-pyrido[4, 3-b]indoles

Russian Chemical Reviews

Volumn 79, Issue 4, 2010, Pages 285-306

  Ivachtchenko, A V ^a,b   Mitkin, O D ^a,b   Kadieva, M G ^a,b   Tkachenko, S E ^a,b  

^a Chemical Diversity Research Institute   (Russian Federation)

^b CHEMDIV INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954799181     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2010v079n04ABEH004122     Document Type: Article

References (132)

1. A-E F Nassar, R E Talaat Drug Discov. Today 9 317 (2004)
2. I Agranat, H Caner, J Caldwell Nat. Rev. Drug Discov. 1 753 (2002)
3. L Hu IDrugs 7 736 (2004)
4. A Burns, R Jacoby Lancet 372 179 (2008)
5. A N Kost, M A Yurovskaya, F A Trofimov Khim. Geterotsikl. Soed. 291 (1973)a
6. A Bridoux, L Goossens, R Houssin, J-P Hganichart J. Heterocycl. Chem. 43 571 (2006)
7. N G Tsyshkova, F ATrofimov Khim.-Farm. Zh. 5 (9) 14 (1971)
8. C A Harbert, J J Plattner, W M Welch, A Weissman, B K Koe J. Med. Chem. 23 635 (1980)
9. W M Welch Synthesis 645 (1977)
10. L A Aksanova, I N Pidevich, L M Sharkova, N F Kucherova Khim.-Farm. Zh. 2 (7) 3 (1968)b
11. A V Ivachtchenko, O D Mit'kin, M G Kadieva, E S Dubrovskaya, I M Okun', S E Tkachenko, Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol. 52 (10) 31 (2009)
12. L Zhang, W Meier, E Wats, T D Costello, P Ma, C L Ensinger, J M Rodgers, I C Jacobson, P Rajagopalan Tetrahedron Lett. 36 8387 (1995)
13. M E Lizarzaburu, S J Shuttleworth Tetrahedron Lett. 45 4781 (2004)
14. C J Cattanach, A Cohen, B Heath-Brown J. Chem. Soc., C 1235 (1968)
15. R G W Spickett J. Med. Chem. 9 436 (1966)
16. N F Kucherova, N K Kochetkov Zh. Obshch. Khim. 26 3149 (1956)c
17. WO 2008112280; Chem. Abstr. 149 378917 (2008)
18. A V Ivachtchenko, O D Mit'kin, I V Kuznetsova, M G Kadieva, A N Ivchenko, Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol. 52 (10) 38 (2009)
19. A N Kost, E V Vinogradova, F A Trofimov, T I Mikhanova, V I Nozdrich, K S Shadurskii Khim.-Farm. Zh. 1 (7) 25 (1967)b
20. V A Zagorevskii, N F Kucherova, N M Sharkova, T I Ivanova, S M Klyuev Khim. Geterotsikl. Soedin. 1353 (1975)a
21. U Hörlein Chem. Ber. 87 463 (1954)
22. A N Kost, E V Vinogradova, Kh Daut, A P Terent'ev Zh. Obshch. Khim. 32 2050 (1962)c
23. T Lee, A J Robichaud, K E Boyle, Y Lu, D W Robertson, K J Miller, L W Fitzgerald, J F McElroyb, B L Largent Bioorg. Med. Chem. Lett. 13 767 (2003)
24. M K Eberle, G G Kahle, S M Talati Tetrahedron 29 4045 (1973)
25. S R Prakash, K M Cable, I D Correa, I Fellows, S Montgomery, J J Newman, I Waterhouse, G N Wells, D R Sutherland J. Label. Compd. Radiopharm. 36 993 (1995)
26. C J Cattanach, A Cohen, B Heath-Brown J. Chem. Soc., C 359 (1971)
27. A Ebnöther, P Niklaus, R Süess Helv. Chim. Acta 52 629 (1969)
28. V Padmavathi, T V R Reddy, K A Reddy, A Padmaja, D B Reddy Indian J. Chem., Sect. B 44 2527 (2005)
29. R E Mewshaw, R G Sherrill, R M Mathew, C Kaiser, M A Bailey, E W Karbon J. Med. Chem. 36 343 (1993)
30. R E Mewshaw, L S Silverman, R M Mathew, C Kaiser, R G Sherrill, M Cheng, C W Tiffany, E W Karbon, M A Bailey, S A Borosky, J W Ferkany, M E Abreu J. Med. Chem. 36 1488 (1993)
31. J T Braunholtz, F G Mann J. Chem. Soc. 381 (1955)
32. C-y Chen, D R Lieberman, R D Larsen, T R Verhoeven, P J Reider J. Org. Chem. 62 2676 (1997)
33. H Iida, Y Yuasa, C Kibayashi J. Org. Chem. 45 2938 (1980)
34. N Moskalev, M Barbasiewicz, M Makosza Tetrahedron 60 347 (2004)
35. L V Kudzma Synthesis 1661 (2003)
36. T A Engler, J Wanner J. Org. Chem. 65 2444 (2000)
37. T A Engler, J Wanner Tetrahedron Lett. 38 6135 (1997)
38. N Valls, V M Segarra, X López, J Bosch Heterocycles 29 231 (1989)
39. F A Trofimov, V I Garnova, A N Grinev, N G Tsyshkova Khim. Geterotsikl. Soedin. 72 (1979)a
40. N N Komzolova, N F, Kucherova, V A Zagorevskii Khim. Geterotsikl. Soedin. 668 (1968)a
41. K Bhandari, V A Murti, P C Jain, N Anand Indian J. Chem., Sect. B 17 246 (1979)
42. R J Sundberg, J D Bloom J. Org. Chem. 46 4836 (1981)
43. S Cutri, A Diez, M Bonin, L Micouin, H-P Husson Org. Lett. 7 1911 (2005)
44. M Salas, I K Al-Khawaja, M J Thomas, J A Joule J. Chem. Res. (S) 7 218 (1988)
45. R Grigg, V Sridharan, D A Sykes Tetrahedron 64 8952 (2008)
46. J Kraxner, P Gmeiner Synthesis 1081 (2000)
47. P Molina, J Alcantara, C Lopez-Leonardo Tetrahedron 52 5833 (1996)
48. M Abou-Gharbia, U R Patel, M B Webb, J A Moyer, T H Andree, E A Muth J. Med. Chem. 30 1818 (1987)
49. M Decker, R Faust, M Wedig, M Nieger, U Holzgrabe, J Lehmann Heterocycles 55 1455 (2001)
50. J M Bobbitt, C L Kulkarni, C P Dutta, H Kofod, K N Chiong J. Org. Chem. 43 3541 (1978)
51. J H Wynne, W M Stalick J. Org. Chem. 68 4845 (2003)
52. E M Beccalli, G Broggini, A Marchesini, E Rossi Tetrahedron 58 6673 (2002)
53. H Ohno, A Aso, Y Kadoh, N Fujii, T Tanaka Angew. Chem., Int. Ed. 46 6325 (2007)
54. M Bandini, A Melloni, F Piccinelli, R Sinisi, S Tommasi, A Umani-Ronchi J. Am. Chem. Soc. 128 1424 (2006)
55. R Grigg, T Coulter Tetrahedron Lett. 32 1359 (1991)
56. Y Shimoji, T Hashimoto, H Yanagisawa Heterocycles 36 123 (1993)
57. A Padwa, S M Lynch, J M Mejta-Oneto, H Zhang J. Org. Chem. 70 2206 (2005)
58. N N Smolyar, A S Volchkov, Yu M Yutilov Khim.-Farm. Zh. 35 (9) 514 (2001)b
59. Yu M Yutilov, N N Smolyar, A S Volchkov Khim.-Farm. Zh. 34 (12) 33 (2000)b
60. N N Novikova, I D Silenko, N F Kucherova, V A Zagorevskii Khim. Geterotsikl. Soedin. 1630 (1976)a
61. M L Bennasar, T Roca, M Monerris, D García-Díaz J. Org. Chem. 71 7028 (2006)
62. M L Bennasar, E Zulaica, S Alonso Tetrahedron Lett. 46 7881 (2005)
63. N Khorana, A Purohit, K Herrick-Davis, M Teitler, R A Glennon Bioorg. Med. Chem. 11 717 (2003)
64. A V Ivachtchenko, O D Mit'kin, V M Kisil', S E Tkachenko, in XLV Vserossiiskaya Konferentsiya po Problemam Matematiki, Informatiki, Fiziki i Khimii (Tez. Dokl. Sektsii Khimii), Moskva, 2009 [The XLVth All-Russian Conference on Problems of Mathematics, Informatics, Physics and Chemistry (Abstracts of Reports of Chemistry Section) Moscow, 2009] p. 95
65. M A Seefeld, W H Miller, K A Newlander, W J Burgess, D J Payne, S F Rittenhouse, T D Moore, W E DeWolf, P M Keller, X Qiu, C A Janson, K Vaidya, A P Fosberry, M G Smyth, D D Jaworski, C Slater-Radosti, W F Huffman Bioorg. Med. Chem. Lett. 11 2241 (2001)
66. A V Ivachtchenko, O D Mit'kin, V M Kisil', E B Frolov, S E Tkachenko Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol. 52 (10) 79 (2009)
67. A V Ivachtchenko, E B Frolov, O D Mitkin, V M Kysil, A V Khvat, I M Okun, S E Tkachenko Bioorg. Med. Chem. Lett. 19 3183 (2009)
68. F A Trofimov, A N Kost, N G Tsyshkova, K S Shadurskii, E V Vinogradova Khim.-Farm. Zh. 1 (3) 22 (1967)b
69. A V Ivachtchenko, E B Frolov, O D Mit'kin, S E Tkachenko, A V Khvat Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol. 52 (10) 55 (2009)
70. A N Kost, M A Yurovskaya, T V Mel'nikova, O I Potanina Khim. Geterotsikl. Soedin. 207 (1973)a
71. B A Trofimov, R N Nesterenko, A I Mikhaleva, A B Shapiro, I A Aliev, I V Yakovleva, G A Kalabin Khim. Geterotsikl. Soedin. 481 (1986)a
72. A V Ivachtchenko, E B Frolov, O D Mitkin, S E Tkachenko, I M Okun, A V Khvat Bioorg. Med. Chem. Lett. 20 78 (2010)
73. A V Ivachtchenko, E B Frolov, O D Mitkin, V M Kysil, A V Khvat, S E Tkachenko Arch. Pharm. 342 740 (2009)
74. C A Harbert, J J Plattner,W M Welch, A Weissman, B K Koe Mol. Pharmacol. 17 38 (1979)
75. A V Ivachtchenko, O D Mitkin, S E Tkachenko, I M Okun, V M Kysil Eur. J. Med. Chem. 45 782 (2010)
76. K S Bhandari, V Snieckus Synthesis 327 (1971)
77. Br. P. 733123; Chem. Abstr. 50 57189 (1956)
78. BRD P. 930444; Chem. Abstr. 52 113832 (1958)
79. US P. 3522262; Chem. Abstr. 73 120600 (1970)
80. B K Koe, A Weissman, J J Plattner, C A Harbert, W I MWelch Pharmacologist 21 180 (1979)
81. Yu G Verkhovskii, L P Kokina Farmakol. Toksikol. 209 (1968)
82. Russ. P. 2106864; Byull. Izobret. (8) 323 (1998)
83. R S Doody, S I Gavrilova, M Sano, R G Thomas, P S Aisen, S O Bachurin, L Seely, D Hung Lancet 372 207 (2008)
84. WO 2007041697; Chem. Abstr. 146 395317 (2007)
85. WO 2006058088; Chem. Abstr. 145 27846 (2006)
86. WO 2005089764; Chem. Abstr. 143 347332 (2005)
87. US P. 3535326; Chem. Abstr. 74 125428 (1971)
88. D A Kharkevich Farmakol. Toksikol. 6 (1967)
89. WO 1999012926; Chem. Abstr. 130 237551 (1999)
90. M D Mashkovskii Lekarstvennye Sredstva ( Pharmaceutical Drugs) Vol.1 (Khar'kov: Torsing, 1998)
91. Russ. P. 2339637; Byull. Iizobret. (33) 818 (2008)
92. WO 9715225; Chem. Abstr. 126 338861 (1997)
93. USSR author's certificate 1138164; Chem. Abstr. 102 198010 (1985)
94. WO 2009055828; Chem. Abstr. 150 494843 (2009)
95. Russ. P. 2338745; Byull. Izobret. (32) 799 (2008)
96. V Boekelheide, C Ainsworth J. Am. Chem. Soc. 72 2132 (1950)
97. A A Kurland, A Nagaraju, T E Hanlon J. Clin. Pharmacol. 22 441 (1982)
98. WO 2000037466; Chem. Abstr. 133 74013 (2000)
99. A M Ismaiel, M Dukat, D L Nelson, V L Lucaites, R A Glennon Med. Chem. Res. 6 197 (1996)
100. N Khorana, C Smith, K Herrick-Davis, A Purohit, M Teitler, B Grella, M Dukat, R A Glennon J. Med. Chem. 46 3930 (2003)
101. S H Snyder, B L Largent J. Neuropsychiatry 1 7 (1989)
102. J Boksa, S Charakchieva-Minol, B Duszyñska, R Bugno, A Klodziñska, E Tatarczyñska, E Chojnacka-Wójcik, A J Bojarski Pol. J. Pharmacol. 55 1013 (2003)
103. Russ. P. 2329044; Byull. Izobret. (20) 793 (2008)
104. WO 2009082268; Chem. Abstr. 151 123969 (2009)
105. S E Tkachenko, A I Ivachtchenko, A V Khvat, Y V Lavrovsky, I M Okun, in Proceedings of the 1st International Conference on Drug Design and Discovery, Dubai, 2008 p. 187
106. S E Tkachenko, A I Ivachtchenko, A V Khvat, Y V Lavrovsky, I M Okun, in Proceedings of the 11th International Conference on Alzheimer's Disease and Related Disorders, Chicago, 2008 P2-478
107. S E Tkachenko, A V Khvat, Y V Lavrovsky, I M Okun, A I Ivachtchenko, in Proceedings of the XXth International Symposium on Medicinal Chemistry, Vienna, 2008 P021
108. Russ. P. 2374245; Byull. Izobret. (33) 618 (2009)
109. Russ. P. 2227028; Byull. Izobret. (11) 459 (2004)
110. N N Lermontova, A E Redkozubov, E F Shevtsova, T P Serkova, E G Kireeva, S O Bachurin Byull. Eksperim. Biol. Med. 132 545 (2001)
111. V V Grigor'ev, O A Dranyi, S O Bachurin Byull. Eksperim. Biol. Med. 136 535 (2003)
112. N N Lermontova, N V Lukoyanov, T P Serkova, E A Lukoyanova, S O Bachurin Byull. Eksperim. Biol. Med. 129 640 (2000)
113. S O Bachurin, E P Shevtsova, E G Kireeva, G F Oxenkrug, S O Sablin Ann. N.Y. Acad. Sci. 993 334 (2003)
114. D Hung, in Proceedings of the 11th International Conference on Alzheimer's Disease and Related Disorders, Chicago, 2008 S4-04-05
115. I Okun, S E Tkachenko, A Khvat, O Mitkin, V Kazey, A V Ivachtchenko Curr. Alzheimer Res. 7 97 (2010)
116. M Yamashita, T Nonaka, T Ara, F Kametani, V L Buchman, N Ninkina, S O Bachurin, H Akiyama, M Goedert, M Hasegawa FEBS Lett. 583 2419 (2009)
117. B L Roth, D J Sheffler,W K Kroeze Nat. Rev. Drug Discov. 3 353 (2004)
118. Russ. P. 2283108; Byull. Izobret. (25) 441 (2006)
119. Russ. P. 2338533; Byull. Izobret. (22) 694 (2008)
120. P A Galenko-Yaroshevskii, O A Chekanova, V V Skibitskii, V V Bartashevich, A I Khankoeva, T I Polyashova Byull. Eksperim. Biol. Med. 119 375 (1995)
121. P A Galenko-Yaroshevskii, I L Cherednik, V V Bartashevich, Yu R Sheikh-Zade, A I Khankleva Byull. Eksperim. Biol. Med. 124 691 (1997)
122. P A Galenko-Yaroshevskii, Yu R Sheikh-Zade, O A Chekanova, E R Melkumova, V V Bartashevich, A I Khankoeva Byull. Eksperim. Biol. Med. 121 506 (1996)
123. K Kieburtz, M McDermott, T S Voss, J Corey-Bloom, L M Deuel, E R Dorsey, S Factor, M D Geschwind, K Hodgeman, E Kayson, S Noonberg, M Pourfar, K Rabinowitz, B Ravina, J Sanchez-Ramos, L Seely F Walker, A Feigin Arch. Neurol. 67 154 (2010)
124. US P. 3718657; Chem. Abstr. 79 5320 (1973)
125. R A Glennon, J De Vry, D G Spencer, T Glaser Pharmacol. Biochem. Behav. 37 769 (1990)
126. J Castaner, H Koch Drugs Fut. 8 516 (1983)
127. L Hegemann, R Fruchtmann, B Bonnekoh, B H Schmidt, J Trabler, G Mahrle, R Muller-Peddinghaus, L A van Rooijen Arch. Dematol. Res. 283 456 (1991)
128. US P. 6448257; Chem. Abstr. 137 216937 (2002)
129. WO 2005117868; Chem. Abstr. 144 22907 (2005)
130. J Quetin-Leclercq, B Bouzahzah, A Pons, R Greimers, L Angenot, R Bassleer, H Barbason Planta Med. 59 59 (1993)
131. Y-X Cheng, X Luo, M Pourashraf, M Tomaszewski Drugs Fut. 33 (Suppl. A) P031 (2008)
132. A Patchett, R Nargund Ann. Rep. Med. Chem. 35 289 (2000)