Efficient catalyst-free one-pot three-component synthesis of novel spirooxindole derivatives, and their cytotoxic activities

Synthesis (Germany)

Volumn 46, Issue 10, 2014, Pages 1389-1398

  Han, Chao ^a   Zhang, Tao ^a,b   Zhang, Anqi ^a   Wang, Dandan ^a   Shi, Weimin ^a   Tao, Jingchao ^a  

^a ZHENGZHOU UNIVERSITY   (China)

^b XINXIANG MEDICAL UNIVERSITY   (China)

Author keywords

cytotoxins; heterocyclic compounds; multicomponent reactions; polycyclic compounds; spiro compounds

Indexed keywords

CELL CULTURE; SYNTHESIS (CHEMICAL);

CYTOTOXINS; HETEROCYCLIC COMPOUND; MULTI-COMPONENT REACTIONS; POLYCYCLIC COMPOUNDS; SPIRO COMPOUNDS;

CATALYSTS;

2' AMINO 1 METHYL 2,5' DIOXO 6' (1 PHENYLETHYL) 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 1,6' DIBENZYL 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 2,5' DIOXO 6' (1 PHENYLETHYL) 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 2,5' DIOXO 6' PHENYL 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 5 METHYL 2,5' DIOXO 6' (1 PHENYLETHYL) 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 5 NITRO 2,5' DIOXO 6' PHENYL 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 1 BUTYL 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 1 ETHYL 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3'CARBONITRILE; 2' AMINO 6' BENZYL 1 METHYL 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 2,5' DIOXO 7 (TRIFLUOROMETHYL) 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 4 BROMO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 4 CHLORO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 5 BROMO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 5 CHLORO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 5 FLUORO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 5 METHYL 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 5 NITRO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 5,7' DIBROMO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 6 BROMO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; 2' AMINO 6' BENZYL 6 CHLORO 2,5' DIOXO 1,2,6',7' TETRAHYDRO 5'H SPIRO(INDOLE 3,4' PYRANO[2,3 C]PYRROLE) 3' CARBONITRILE; ANTINEOPLASTIC AGENT; CISPLATIN; INDOLE DERIVATIVE; SPIROOXINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYST; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; ONE POT SYNTHESIS; RAJI CELL LINE;

EID: 84900477018     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1341028     Document Type: Article

References (67)

1. Tietze L. F., Modi A. Med. Res. Rev.: 2000; 20 304
2. Zhu J. Eur. J. Org. Chem.: 2003; 1133
3. Karmakar B., Nayak A., Banerji J. Tetrahedron Lett.: 2012; 53 5004
4. Kidwai M., Jain A., Bhardwaj S. Mol. Diversity: 2012; 16 121
5. Orru R. V. A, de Greef M. Synthesis: 2003; 1471
6. Nair V., Rajesh C., Vinod A. U., Bindu S., Sreekanth A. R., Mathen J. S., Balagopal L. Acc. Chem. Res.: 2003; 36 899
7. Simon C., Constantieux T., Rodriguez J. Eur. J. Org. Chem.: 2004; 4957
8. Ramon D. J., Yus M. Angew. Chem. Int. Ed.: 2005; 44 1602
9. Wu Q., Feng H., Guo D.-D, Yi M.-S, Wang X.-H, Jiang B., Tu S.-Q. J. Heterocycl. Chem.: 2013; 50 599
10. Hulme C., Gore V. Curr. Med. Chem.: 2003; 10 51
11. Sunderhaus J. D., Dockendorff C., Martin S. F. Org. Lett.: 2007; 9 4223
12. Liéby-Muller F., Constantieux T., Rodriguez J. J. Am. Chem. Soc.: 2005; 127 17176
13. Knyazeva I. V., Groth U., Glasnov T. N., Kappe C. O. J. Org. Chem.: 2008; 73 5110
14. Zhang X.-N, Li Y.-X, Zhan Z.-H. Tetrahedron: 2011; 67 7426
15. Nakajima T., Yamashita D., Suzuki K., Nakazaki A., Suzuki T., Kobayashi S. Org. Lett.: 2011; 13 2980
16. Aho J. E., Pihko P. M., Rissa T. K. Chem. Rev.: 2005; 105 4406
17. Kotha S., Dipak M. K., Mobin S. M. Tetrahedron: 2011; 67 4616
18. Li J., Li L., Si Y., Jiang X., Guo L., Che Y. Org. Lett.: 2011; 13 2670
19. Chande M. S., Verma R. S., Barve P. A., Khanwelkar R. R., Vaidya R. B., Ajaikumar K. B. Eur. J. Med. Chem.: 2005; 40 1143
20. Palmer L. I., Read de Alaniz J. Angew. Chem. Int. Ed.: 2011; 50 7167
21. Bandichhor R., Lowell A. N., Kozlowski M. C. J. Org. Chem.: 2011; 76 6475
22. Wang G.-D, Zhang X.-N, Zhang Z.-H. J. Heterocycl. Chem.: 2013; 50 61
23. Kornet M. J., Thio A. P. J. Med. Chem.: 1976; 19 892
24. Galliford C. V., Scheidt K. A. Angew. Chem. Int. Ed.: 2007; 46 8748
25. Marti C., Carreira E. M. Eur. J. Org. Chem.: 2003; 2209
26. Yin X.-G, Liu X.-Y, Hu Z.-P, Yan M. Org. Biomol. Chem.: 2012; 10 1506
27. MacDonald J. P., Badillo J. J., Arevalo G. E., Silva-García A., Franz A. K. ACS Comb. Sci.: 2012; 14 285
28. Kidwai M., Jain A., Nemaysh V., Kumar R., Luthra P. M. Med. Chem. Res.: 2013; 22 2717
29. Ball-Jones N. R., Badillo J. J., Franz A. K. Org. Biomol. Chem.: 2012; 10 5165
30. Yu F.-C, Huang R., Ni H.-C, Fan J., Yan S.-J, Lin J. Green Chem.: 2013; 15 453
31. Rahmati A., Khalesi Z. Tetrahedron: 2012; 68 8472
32. Zhou Y.-J, Chen D.-S, Li Y.-L, Liu Y., Wang X.-S. ACS Comb. Sci.: 2013; 15 498
33. Khalafi-Nezhad A., Mohammadi S. ACS Comb. Sci.: 2013; 15 512
34. Kang T. H., Matsumoto K., Murakami Y., Takayama H., Kitajima M., Aimi N., Watanabe H. Eur. J. Pharmacol.: 2002; 444 39
35. Kidwai M., Jahan A., Mishra N. K. Appl. Catal., A: 2012; 425 35
36. Dandia A., Singh R., Khaturia S., Merienne C., Morgant G., Loupy A. Bioorg. Med. Chem.: 2006; 14 2409
37. Sebahar P. R., Williams R. M. J. Am. Chem. Soc.: 2000; 122 5666
38. Edmondson S., Danishefsky S. J., Sepp-Lorenzinol L., Rosen N. J. Am. Chem. Soc.: 1999; 121 2147
39. Royles B. J. L. Chem. Rev.: 1995; 95 1981
40. Schobert R., Schlenk A. Bioorg. Med. Chem.: 2008; 16 4203
41. Singh S. B., Zink D. L., Heimbach B., Genilloud O., Teran A., Silverman K. C., Lingham R. B., Felock P., Hazuda D. J. Org. Lett.: 2002; 4 1123
42. Baraldi P. G., Manfredini S., Simoni D., Tabrizi M. A., Balzarini J., De Clercq E. J. Med. Chem.: 1992; 35 1877
43. Perrella F. W., Chen S.-F, Behrens D. L., Kaltenbach R. F. III, Seitz S. P. J. Med. Chem.: 1994; 37 2232
44. Kashman Y., Gustafson K. R., Fuller R. W., Cardellina J. H. II, McMahon J. B., Currens M. J., Buckheit R. W. Jr, Hughes S. H., Cragg G. M., Boyd M. R. J. Med. Chem.: 1992; 35 2735
45. Patil A. D., Freyer A. J., Eggleston D. S., Haltiwanger R. C., Bean M. F., Taylor P. B., Caranfa M. J., Breen A. L., Bartus H. R., Johnson R. K., Hertzberg R. P., Westley J. W. J. Med. Chem.: 1993; 36 4131
46. Pore D. M., Patil P. B., Gaikwad D. S., Hegade P. G., Patil J. D., Undale K. A. Tetrahedron Lett.: 2013; 54 5876
47. Deng J., Mo L.-P, Zhao F.-Y, Zhang Z.-H, Liu S.-X. ACS Comb. Sci.: 2012; 14 335
48. Jadidi K., Ghahremanzadeh R., Bazgir A. J. Comb. Chem.: 2009; 11 341
49. Litvinov Y. M., Mortikov V. Y., Shestopalov A. M. J. Comb. Chem.: 2008; 10 741
50. Wu C.-L, Shen R.-P, Chen J.-H, Hu C.-Q. Bull. Korean Chem. Soc.: 2013; 34 2431
51. Tisseh Z. N., Ahmadi F., Dabiri M., Khavasi H. R., Bazgir A. Tetrahedron Lett.: 2012; 53 3603
52. Joshi K. C., Jain R., Arora S. J. Indian Chem. Soc.: 1988; 65 277
53. Nandakumar A., Thirumurugan P., Perumal P. T., Vembu P., Ponnuswamy M. N., Ramesh P. Bioorg. Med. Chem. Lett.: 2010; 20 4252
54. Watahiki T., Matsuzaki M., Oriyama T. Green Chem.: 2003; 5 82
55. Watahiki T., Ohba S., Oriyama T. Org. Lett.: 2003; 5 2679
56. Iwanami K., Hinakubo Y., Oriyama T. Tetrahedron Lett.: 2005; 46 5881
57. Khatik G. L., Kumar R., Chakraborti A. K. Org. Lett.: 2006; 8 2433
58. Oriyama T., Aoyagi M., Iwanami K. Chem. Lett.: 2007; 36 612
59. Li Y.-L, Chen H., Shi C.-L, Shi D.-Q, Ji S.-J. J. Comb. Chem.: 2010; 12 231
60. Zhang L.-J, Wu Q., Sun J., Yan C.-G. Beilstein J. Org. Chem.: 2013; 9 846
61. Guo R.-Y, Wang P., Wang G.-D, Mo L.-P, Zhang Z.-H. Tetrahedron: 2013; 69 2056
62. Trost B. M., Brennan M. K. Synthesis: 2009; 3003
63. Xie X., Peng C., He G., Leng H.-J, Wang B., Huang W., Han B. Chem. Commun.: 2012; 48 10487
64. Ramachary D. B., Venkaiah C., Madhavachary R. Org. Lett.: 2013; 15 3042
65. Speelman J. C., Talma A. G., Kellogg R. M., De Boer J. L., Beurskens P. T., Bosman W. P. J. Org. Chem.: 1989; 54 1055
66. Kimura Y., Atarashi S., Kawakami K., Sato K., Hayakawa I. J. Med. Chem.: 1994; 37 3344
67. Park T. H., Paik S., Lee S. H. Bull. Korean Chem. Soc.: 2003; 24 1227