Efficient Catalyst-Free One-Pot Three-Component Synthesis of Novel Spiro­oxindole Derivatives, and Their Cytotoxic Activities

Chao Han; Tao Zhang; Anqi Zhang; Dandan Wang; Weimin Shi; Jingchao Tao

doi:10.1055/s-0033-1341028

Synthesis, Table of Contents

Synthesis 2014; 46(10): 1389-1398
DOI: 10.1055/s-0033-1341028

paper

Efficient Catalyst-Free One-Pot Three-Component Synthesis of Novel Spirooxindole Derivatives, and Their Cytotoxic Activities

Authors

Chao Han

^aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052, Henan, P. R. of China
Tao Zhang

^aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052, Henan, P. R. of China

^bSchool of Pharmacy, Xinxiang Medical University, Xinxiang 453003, Henan, P. R. of China Fax: +86(371)67767200 Email: jctao@zzu.edu.cn
Anqi Zhang

^aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052, Henan, P. R. of China
Dandan Wang

^aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052, Henan, P. R. of China
Weimin Shi

^aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052, Henan, P. R. of China
Jingchao Tao*

^aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052, Henan, P. R. of China

Abstract

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Abstract

A simple and efficient one-pot approach for assembling novel spiro[indolepyranopyrrole] derivatives was developed and used to prepare a series of biologically important compounds. The reaction was easily performed with high efficiency under very simple and mild conditions without any catalysts and it gave good yields, avoiding time-consuming costly synthesis and laborious workup and purification of products. The cytotoxic activities of these new spiro[indolepyranopyrrole] derivatives were evaluated in vitro. Most of the tested compounds exhibited significant cytotoxicities to Raji cell lines.

Key words

polycyclic compounds - heterocyclic compounds - spiro compounds - multicomponent reactions - cytotoxins

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References

References

1a Tietze LF, Modi A. Med. Res. Rev. 2000; 20: 304
1b Zhu J. Eur. J. Org. Chem. 2003; 1133
1c Karmakar B, Nayak A, Banerji J. Tetrahedron Lett. 2012; 53: 5004
1d Kidwai M, Jain A, Bhardwaj S. Mol. Diversity 2012; 16: 121
1e Orru RV. A, de Greef M. Synthesis 2003; 1471

2a Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L. Acc. Chem. Res. 2003; 36: 899
2b Simon C, Constantieux T, Rodriguez J. Eur. J. Org. Chem. 2004; 4957
2c Ramon DJ, Yus M. Angew. Chem. Int. Ed. 2005; 44: 1602
2d Wu Q, Feng H, Guo D.-D, Yi M.-S, Wang X.-H, Jiang B, Tu S.-Q. J. Heterocycl. Chem. 2013; 50: 599

3a Hulme C, Gore V. Curr. Med. Chem. 2003; 10: 51
3b Sunderhaus JD, Dockendorff C, Martin SF. Org. Lett. 2007; 9: 4223
3c Liéby-Muller F, Constantieux T, Rodriguez J. J. Am. Chem. Soc. 2005; 127: 17176
3d Knyazeva IV, Groth U, Glasnov TN, Kappe CO. J. Org. Chem. 2008; 73: 5110
3e Zhang X.-N, Li Y.-X, Zhan Z.-H. Tetrahedron 2011; 67: 7426

4a Nakajima T, Yamashita D, Suzuki K, Nakazaki A, Suzuki T, Kobayashi S. Org. Lett. 2011; 13: 2980
4b Aho JE, Pihko PM, Rissa TK. Chem. Rev. 2005; 105: 4406
4c Kotha S, Dipak MK, Mobin SM. Tetrahedron 2011; 67: 4616
4d Li J, Li L, Si Y, Jiang X, Guo L, Che Y. Org. Lett. 2011; 13: 2670

5a Chande MS, Verma RS, Barve PA, Khanwelkar RR, Vaidya RB, Ajaikumar KB. Eur. J. Med. Chem. 2005; 40: 1143
5b Palmer LI, Read de Alaniz J. Angew. Chem. Int. Ed. 2011; 50: 7167
5c Bandichhor R, Lowell AN, Kozlowski MC. J. Org. Chem. 2011; 76: 6475
5d Wang G.-D, Zhang X.-N, Zhang Z.-H. J. Heterocycl. Chem. 2013; 50: 61

6a Kornet MJ, Thio AP. J. Med. Chem. 1976; 19: 892
6b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
6c Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209

7a Yin X.-G, Liu X.-Y, Hu Z.-P, Yan M. Org. Biomol. Chem. 2012; 10: 1506
7b MacDonald JP, Badillo JJ, Arevalo GE, Silva-García A, Franz AK. ACS Comb. Sci. 2012; 14: 285

8a Kidwai M, Jain A, Nemaysh V, Kumar R, Luthra PM. Med. Chem. Res. 2013; 22: 2717
8b Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165

9a Yu F.-C, Huang R, Ni H.-C, Fan J, Yan S.-J, Lin J. Green Chem. 2013; 15: 453
9b Rahmati A, Khalesi Z. Tetrahedron 2012; 68: 8472
9c Zhou Y.-J, Chen D.-S, Li Y.-L, Liu Y, Wang X.-S. ACS Comb. Sci. 2013; 15: 498
9d Khalafi-Nezhad A, Mohammadi S. ACS Comb. Sci. 2013; 15: 512

10a Kang TH, Matsumoto K, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H. Eur. J. Pharmacol. 2002; 444: 39
10b Kidwai M, Jahan A, Mishra NK. Appl. Catal., A 2012; 425: 35

11a Dandia A, Singh R, Khaturia S, Merienne C, Morgant G, Loupy A. Bioorg. Med. Chem. 2006; 14: 2409
11b Sebahar PR, Williams RM. J. Am. Chem. Soc. 2000; 122: 5666
11c Edmondson S, Danishefsky SJ, Sepp-Lorenzinol L, Rosen N. J. Am. Chem. Soc. 1999; 121: 2147

12a Royles BJ. L. Chem. Rev. 1995; 95: 1981
12b Schobert R, Schlenk A. Bioorg. Med. Chem. 2008; 16: 4203
12c Singh SB, Zink DL, Heimbach B, Genilloud O, Teran A, Silverman KC, Lingham RB, Felock P, Hazuda DJ. Org. Lett. 2002; 4: 1123

13 Bonsignore L, Loy G, Secci D, Calignano A. Eur. J. Med. Chem. 1993; 28: 517

14a Baraldi PG, Manfredini S, Simoni D, Tabrizi MA, Balzarini J, De Clercq E. J. Med. Chem. 1992; 35: 1877
14b Perrella FW, Chen S.-F, Behrens DL, Kaltenbach RF. III, Seitz SP. J. Med. Chem. 1994; 37: 2232

15a Kashman Y, Gustafson KR, Fuller RW, Cardellina JH. II, McMahon JB, Currens MJ, Buckheit RW. Jr, Hughes SH, Cragg GM, Boyd MR. J. Med. Chem. 1992; 35: 2735
15b Patil AD, Freyer AJ, Eggleston DS, Haltiwanger RC, Bean MF, Taylor PB, Caranfa MJ, Breen AL, Bartus HR, Johnson RK, Hertzberg RP, Westley JW. J. Med. Chem. 1993; 36: 4131

16a Pore DM, Patil PB, Gaikwad DS, Hegade PG, Patil JD, Undale KA. Tetrahedron Lett. 2013; 54: 5876
16b Deng J, Mo L.-P, Zhao F.-Y, Zhang Z.-H, Liu S.-X. ACS Comb. Sci. 2012; 14: 335
16c Jadidi K, Ghahremanzadeh R, Bazgir A. J. Comb. Chem. 2009; 11: 341
16d Litvinov YM, Mortikov VY, Shestopalov AM. J. Comb. Chem. 2008; 10: 741
16e Wu C.-L, Shen R.-P, Chen J.-H, Hu C.-Q. Bull. Korean Chem. Soc. 2013; 34: 2431

17a Tisseh ZN, Ahmadi F, Dabiri M, Khavasi HR, Bazgir A. Tetrahedron Lett. 2012; 53: 3603
17b Joshi KC, Jain R, Arora S. J. Indian Chem. Soc. 1988; 65: 277
17c Nandakumar A, Thirumurugan P, Perumal PT, Vembu P, Ponnuswamy MN, Ramesh P. Bioorg. Med. Chem. Lett. 2010; 20: 4252

18a Watahiki T, Matsuzaki M, Oriyama T. Green Chem. 2003; 5: 82
18b Watahiki T, Ohba S, Oriyama T. Org. Lett. 2003; 5: 2679

19a Iwanami K, Hinakubo Y, Oriyama T. Tetrahedron Lett. 2005; 46: 5881
19b Khatik GL, Kumar R, Chakraborti AK. Org. Lett. 2006; 8: 2433
19c Oriyama T, Aoyagi M, Iwanami K. Chem. Lett. 2007; 36: 612

20a Li Y.-L, Chen H, Shi C.-L, Shi D.-Q, Ji S.-J. J. Comb. Chem. 2010; 12: 231
20b Zhang L.-J, Wu Q, Sun J, Yan C.-G. Beilstein J. Org. Chem. 2013; 9: 846
20c Guo R.-Y, Wang P, Wang G.-D, Mo L.-P, Zhang Z.-H. Tetrahedron 2013; 69: 2056

21a Trost BM, Brennan MK. Synthesis 2009; 3003
21b Xie X, Peng C, He G, Leng H.-J, Wang B, Huang W, Han B. Chem. Commun. 2012; 48: 10487
21c Ramachary DB, Venkaiah C, Madhavachary R. Org. Lett. 2013; 15: 3042

22a Speelman JC, Talma AG, Kellogg RM, De Boer JL, Beurskens PT, Bosman WP. J. Org. Chem. 1989; 54: 1055
22b Kimura Y, Atarashi S, Kawakami K, Sato K, Hayakawa I. J. Med. Chem. 1994; 37: 3344
22c Park TH, Paik S, Lee SH. Bull. Korean Chem. Soc. 2003; 24: 1227

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Efficient Catalyst-Free One-Pot Three-Component Synthesis of Novel Spiro­oxindole Derivatives, and Their Cytotoxic Activities

Authors

Efficient Catalyst-Free One-Pot Three-Component Synthesis of Novel Spirooxindole Derivatives, and Their Cytotoxic Activities