Simple three-component method for the synthesis of spiroindeno[1,2-b] pyrido[2,3-d]pyrimidine-5,3′-indolines

ACS Combinatorial Science

Volumn 13, Issue 1, 2011, Pages 96-99

  Imani Shakibaei, Ghazaleh ^a   Feiz, Afsaneh ^a   Reza Khavasi, Hamid ^a   Abolhasani Soorki, Ali ^a   Bazgir, Ayoob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Acenaphthylene 1,2 dione; Amino uracils; Catalyst free; Isatins; Spiroacenaphthylene 1,4 indeno 1,5 pyrido 2,3 d pyrimidines; Spiroindeno 1,2 b pyrido 2,3 d pyrimidine 5,3 indolines

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; MICROBIOLOGICAL EXAMINATION; SYNTHESIS;

INDOLES; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR;

EID: 78651454144     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co1000053     Document Type: Article

References (45)

1. Bacelar, A. H.; Carvalho, M. A.; Proença, M. F. Eur. J. Med. Chem. 2010, 45, 3234-3239
2. Amin, K. M.; Hanna, M. M.; Abo-Youssef, H. E.; George, R. F. Eur. J. Med. Chem. 2009, 44, 4572-4584
3. Lin, W.; Buolamwini, J. K. J. Med. Chem. 2007, 50, 3906-3920
4. Curtin, N. J.; Barlow, H. C.; Bowman, K. J.; Calvert, A. H.; Davison, R.; Golding, B. T.; Huang, B.; Loughlin, P. J.; Newell, D. R.; Smith, P. G.; Griffin, R. J. J. Med. Chem. 2004, 47, 4905-4922
5. Ram, V. J.; Goel, A.; Sarkhel, S.; Maulik, P. R. Bioorg. Med. Chem. 2002, 10, 1275-1280
6. Tenser, R. B.; Gaydos, A.; Hay, K. A. Antimicrob. Agents Chemother. 2001, 45, 3657-3659
7. Rewcastle, G. W.; Bridges, A. J.; Fry, D. W.; Rubin, J. R.; Denny, W. A. J. Med. Chem. 1997, 40, 1820-1826
8. Fry, D. W.; Becker, M. A.; Switzer, R. L. Mol. Pharmacol. 1995, 47, 810-815
9. Gebauer, M. G.; McKinlay, C.; Gready, J. E. Eur. J. Med. Chem. 2003, 38, 719-728
10. Tu, S.; Zhang, J.; Zhu, X.; Xu, J.; Zhang, Y.; Wang, Q.; Jia, R.; Jiang, B.; Zhang, J. Bioorg. Med. Chem. Lett. 2006, 16, 3578-3561
11. Agarwal, A.; Chauhan, P. M. S. Synth. Commun. 2004, 34, 4447-4461
12. Quiroga, J.; Cisneros, C.; Insuasty, B.; Abonía, R.; Nogueras, M.; Sánchez, A. Tetradehron Lett. 2001, 42, 5625-5627
13. Devi, I.; Kumar, B. S. D.; Bhuyan, P. J. Tetrahedron Lett. 2003, 44, 8307-8310
14. Quiroga, J.; Cisneros, C.; Insuasty, B.; Abonía, Silvia Cruz, R.; Nogueras, M.; de la Torre, J. M.; Sortino, M.; Zacchino, S. J. Heterocycl. Chem. 2006, 43, 299-306
15. Zhang, J.; El-Shabrawy, A.-R. O.; El-Shanawany, M. A.; Schiff, P. L.; Slatkin, D. J. J. Nat. Prod. 1987, 50, 800-806
16. Nugiel, D. A.; Etzkorn, A.-M.; Vidwans, A.; Benfield, P. A.; Boisclair, M.; Burton, C. R.; Cox, S.; Czerniak, P. M.; Doleniak, D.; Seitz, S. P. J. Med. Chem. 2001, 44, 1334-1336
17. Féderick, R.; Dumont, W.; Ooms, F.; Aschenbach, L.; Van der Schyf, C. J.; Castagnoli, N.; Wouters, J.; Krief, A. J. Med. Chem. 2006, 49, 3743-3747
18. Anzini, M.; Cappelli, A.; Vomero, S.; Cagnotto, A.; Skorupska, M. Med. Chem. Res. 1993, 3, 44-51
19. Quraishi, A. M.; Thakur, V. R.; Dhawan, S. N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1989, 28B, 891-892
20. Sundberg, R. J. The Chemistry of Indoles; Academic: New York, NY, 1996.
21. Joshi, K. C.; Chand, P. Pharmazie 1982, 37, 1-12
22. Da-Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273-324
23. Abdel-Rahman, A. H.; Keshk, E. M.; Hanna, M. A.; El-Bady, Sh. M. Bioorg. Med. Chem. 2004, 12, 2483-2488
24. Zhu, S.-L.; Ji, S.-J.; Yong, Z. Tetrahedron 2007, 63, 9365-9372
25. Kang, T.-H.; Matsumoto, K.; Murakami, Y.; Takayama, H.; Kitajima, M.; Aimi, N.; Watanabe, H. Eur. J. Pharmacol. 2002, 444, 39-45
26. Ma, J.; Hecht, S. M. Chem. Commun. 2004, 1190-1191
27. Usui, T.; Kondoh, M.; Cui, C.-B.; Mayumi, T.; Osada, H. Biochem. J. 1998, 333, 543-548
28. Khafagy, M. M.; El-Wahas, A. H. F. A.; Eid, F. A.; El-Agrody, A. M. Farmaco 2002, 57, 715-722
29. Ahadi, S.; Ghahremanzadeh, R.; Mirzaei, P.; Bazgir, A. Tetrahedron 2009, 65, 9316-9321
30. Jadidi, K.; Ghahremanzadeh, R.; Bazgir, A. J. Comb. Chem. 2009, 11, 341-344
31. Ghahremanzadeh, R.; Sayyafi, M.; Ahadi, S.; Bazgir, A. J. Comb. Chem. 2009, 11, 393-396
32. Ghahremanzadeh, R.; Ahadi, S.; Imani Shakibaei, G.; Bazgir, A. Tetrahedron Lett. 2010, 51, 499-502
33. Ghahremanzadeh, R.; Imani Shakibaei, G.; Ahadi, S.; Bazgir, A. J. Comb. Chem. 2010, 12, 191-194
34. Ghahremanzadeh, R.; Amanpoor, T.; Bazgir, A. J. Heterocycl. Chem. 2009, 46, 1266-1270
35. Ghahremanzadeh, R.; Amanpoor, T.; Sayyafi, M.; Bazgir, A. J. Heterocycl. Chem. 2010, 47, 421-424
36. Ghahremanzadeh, R.; Amanpoor, T.; Bazgir, A. J. Heterocycl. Chem. 2010, 47, 46-49
37. Zhu, S.-L.; Ji, S.-J.; Zhang, Y. Tetrahedron 2007, 63, 9365-9372
38. Redkin, R. Gr.; Shemchuk, L. A.; Chernykh, V. P.; Shishkin, O. V.; Shishkina, S. V. Tetrahedron 2007, 63, 11444-11450
39. Shanthi, G.; Subbulakshmi, G.; Perumal, P. T Tetrahedron 2007, 63, 2057-2063
40. Wang, L.-M.; Jiao, N.; Qiu, J.; Yu, J.-J.; Liu, J.-G.; Guo, F.-L.; Liu, Y. Tetrahedron 2010, 66, 339-343
41. Dabiri, M.; Bahramnejad, M.; Baghbanzadeh, M. Tetrahedron 2009, 65, 9443-9447
42. Litviniv, Y. M.; Mortikov, V. Y.; Shestopalov, A. M. J. Comb. Chem. 2008, 10, 741-745
43. 2 = 0.2454, and S = 1.098 with 330 parameters using 6211 independent reflection (- range = 1.98-29.27°). Hydrogen atoms were located from expected geometry and were not refined. Crystallographic data for 4 { 1, 5 } have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained, free of charge, on application to The Director, CCDC 789416, Union Road, Cambridge CB2 1EZ, U.K. Fax: +44 1223 336033. E-mail: deposit@ccdc.cam.ac.uk.
44. NCCLS. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, which Grows Aerobically, 5 th ed.; Approved Standard M7-A5; NCCLS: Villanova, PA, 2000.
45. X-STEP32, version 1.07b, X-ray structure evaluation package; Stoe & Cie: Darmstadt, Germany, 2000.