Synthesis of new class of spirocarbocycle derivatives by multicomponent domino reaction and their evaluation for antimicrobial, anticancer activity and molecular docking studies

European Journal of Medicinal Chemistry

Volumn 83, Issue , 2014, Pages 190-207

  Sudhapriya, N ^a   Perumal, P T ^a   Balachandran, C ^b   Ignacimuthu, S ^b   Sangeetha, M ^c   Doble, Mukesh ^c  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

^b LOYOLA COLLEGE   (India)

^c INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Anticancer activity; Antimicrobial activity; Molecular docking; Multicomponent reaction; Spirocarbocycle; Vinylogous Michael addition

Indexed keywords

3 AMINO 1 (4 CHLOROPHENYL) 1',3' DIOXO 1,1',3',6,7,8,9,9A OCTAHYDROSPIRO(BENZO[7]ANNULENE 2,2' INDENE) 4 CARBONITRILE; 3 AMINO 1',3' DIOXO 1 4 TOLYL 1,1',3',6,7,8,9,9A OCTAHYDROSPIRO(BENZO[7]ANNULENE 2,2' INDENE) 4 CARBONITRILE; 3 AMINO 2' OXO 1 4 TOLYL 1,6,7,8,9,9A HEXAHYDROSPIRO(BENZO[7]ANNULENE 2,3' INDOLINE) 4 CARBONITRILE; 3' AMINO 1' (2 FLUOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (2 FLUOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 BROMOPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 BROMOPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2 NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 CHLOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4 ' CARBONITRILE; 3' AMINO 1' (4 CHLOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3'2 NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 METHOXYPHENYL) 2 OXO 6' ,7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 METHOXYPHENYL) 2,6 DIOXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(CYCLOHEXANE 1,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4AMETHOXYPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (FURAN 3 YL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (FURAN 3 YL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (NAPHTHALEN 1 YL) 1,3 DIOXO 1,3,6' ,7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (NAPHTHALEN 1 YL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2 NAPHTHALENE 4' CARBONITRILE; 3' AMINO 1,3 DIOXO 1' (THIOPHEN 2 YL) 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1,3 DIOXO 1' 4 TOLYL 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 2 OXO 1' (PYRIDIN 2 YL) 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 2 OXO 1' (THIOPHEN 2 YL) 6',7',8',8A' ETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE 4' CARBONITRILE; 3' AMINO 2 OXO 1' 4 TOLYL 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3.3 NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 2,6 DIOXO 1' 4 TOLYL 6',7',8',8A' TETRAHYDRO 1'H SPIROCYCLOHEXANE 1,2' NAPHTHALENE) 4' CARBONITRILE; 6 AMINO 1',3' DIOXO 4 4 TOLYL 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI[INDENE] 7 CARBONITRILE; 6 AMINO 4 (2 FLUOROPHENYL) 1',3' DIOXO 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE; 6 AMINO 4 (4 METHOXYPHENYL) 1',3' DIOXO 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; KETOCONAZOLE; SPIRO COMPOUND; STREPTOMYCIN; UNCLASSIFIED DRUG; 3 AMINO 1',3' DIOXO 1 PARA TOLYL 1,1',3',6,7,8,9,9A OCTAHY DROSPIRO(BENZO[7]ANNULENE 2,2' INDENE) 4 CARBONITRILE; 3 AMINO 1,3 DIOXO 1' PARA TOLYL 1,3,6 ,7 ,8 ,8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE] 4' CARBONITRILE; 3 AMINO 2 OXO 1 PARA TOLYL 1,6,7,8,9,9A HEXAHYDROSPIRO(BENZO [7]ANNULENE 2,3' INDOLINE) 4 CARBONITRILE; 3' AMINO 1' (2 FLUOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4 CARBONITRILE; 3' AMINO 1' (2 FLUOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 BROMOPHENYL) 1,3 DIOXO 1,3,6',7' ,8',8A' HEXAHYDRO 1' SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARNONITRILE; 3' AMINO 1' (4 BROMOPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 CHLOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 CHLOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 METHOXYPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (4 METHOXYPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (FURAN 3 YL) 1,3 DIOXO 1,3,6',7' ,8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (FURAN 3 YL) 2 OXO 6' ,7',8',8A' TETRAHYDRO 1'H SPIRO[INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (NAPHTHALEN 1 YL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 1' (NAPHTHALEN 1 YL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 2 OXO 1' (THIOPHEN 2 YL) 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE; 3' AMINO 2 OXO 1' PARA TOLYL 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE; 6 AMINO 1',3' DIOXO 4 PARA TOLYL 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; INDENE DERIVATIVE; UNINDEXED DRUG; ANAPLASTIC LYMPHOMA KINASE; DNA TOPOISOMERASE (ATP HYDROLYSING); PROTEIN TYROSINE KINASE;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL LINE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DISK DIFFUSION; DRUG SCREENING; DRUG SYNTHESIS; ENTEROBACTER AEROGENES; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; LUNG ADENOCARCINOMA; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; PROTEUS VULGARIS; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY; SALMONELLA TYPHIMURIUM; SHIGELLA FLEXNERI; STAPHYLOCOCCUS EPIDERMIDIS; SUBSTITUTION REACTION; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; IC50; IN VITRO STUDY; REACTION ANALYSIS; SALMONELLA ENTERICA SUBSP. ENTERICA SEROVAR TYPHIMURIUM; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY; BACTERIA; CHEMISTRY; DRUG EFFECTS; METABOLISM; PROTEIN CONFORMATION; SYNTHESIS; TUMOR CELL LINE;

ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BACTERIA; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, SYNTHETIC; DNA GYRASE; HUMANS; MOLECULAR DOCKING SIMULATION; PROTEIN CONFORMATION; RECEPTOR PROTEIN-TYROSINE KINASES; SPIRO COMPOUNDS;

EID: 84903177596     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.065     Document Type: Article

References (45)

1. A.S. Girgis Eur. J. Med. Chem. 44 2009 91 100
2. C. Young-Won, S. Angela, S. Bao-Ning, M. Qiuwen, C. Hee-Byung, R. Soedarsono, K. Leonardus, R. Agus, F. Norman, S. Steven, and K. Douglas J. Nat. Prod. 71 2008 390 395
3. R. Murugan, S. Anbazhagan, and S.S. Narayanan Eur. J. Med. Chem. 44 2009 3272 3279
4. S.A. Van der Sar, J.W. Blunt, and M.H. Munro Org. Lett. 8 2006 2059 2061
5. P. Prasanna, K. Balamurugan, S. Perumal, P. Yogeeswari, and D. Sriram Eur. J. Med. Chem. 45 2010 5653 5661
6. S.V. Karthikeyan, B.D. Bala, V.P.A. Raja, S. Perumal, P. Yogeeswari, and D. Sriram Bioorg. Med. Chem. Lett. 20 2010 350 353
7. K.M. Amin, M.M. Kamel, M.M. Anwar, M. Khedr, and Y.M. Syam Eur. J. Med. Chem. 45 2010 2117 2131
8. M.J. Pawar, A.B. Burungale, and B.K. Karale Arkivoc Part XIII 2009 97 107
9. B. Thadhaney, D. Sain, G. Pernawat, and G.L. Talesara Indian J. Chem. 49B 2010 368 373
10. M. Li, F.M. Gong, L.R. Wen, and Z.R. Li Eur. J. Org. Chem. 2011 3482 3490
11. S. Bruch, S.S.V. Berkel, and B. Westermann Chem. Soc. Rev. 42 2013 4948 4962
12. Y.C. Chen, D. Xue, J.G. Deng, X. Cui, J. Zhu, and Y.Z. Jiang Tetrahedron Lett. 45 2004 1555 1558
13. D. Xue, Y.C. Chen, X. Cui, Q.W. Wang, J. Zhu, and J.G. Deng J. Org. Chem. 70 2005 3584 3591
14. D. Xue, Y.C. Chen, L.F. Cun, Q.W. Wang, J. Zhu, and J.G. Deng Org. Lett. 7 2005 5293 5296
15. J.W. Xie, L. Yue, D. Xue, X.L. Ma, Y.C. Chen, Y. Wu, J. Zhu, and J.G. Deng Chem. Commun. 2006 1563 1565
16. J.W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.C. Chen, Y. Wu, J. Zhu, and J.G. Deng Angew. Chem. Int. Ed. 46 2007 389 392
17. T.B. Poulsen, C. Alemparte, and K.A. Jørgensen J. Am. Chem. Soc. 127 2005 11614 11615
18. T.B. Poulsen, M. Bell, and K.A. Jørgensen Org. Biomol. Chem. 4 2006 2001 2011
19. M.N. Elinson, A.I. Ilovaisky, V.M. Merkulova, F. Barba, and B. Batanero Tetrahedron 69 2013 7125 7130
20. Naoto Chatani, and Terukiyo Hanafusa Bull. Chem. Soc. Jpn. 63 1990 2134 2135
21. A.K. El-Shafei, A.A. Sultan, A.M. Soliman, and E.A. Ahmed Synth. Commun. 25 1995 3211 3217
22. J. Ficini, G. Revial, and J.P. Genêt Tetrahedron Lett. 22 1981 629 632
23. R. Kaiser, and P. Naegeli Tetrahedron Lett. 13 1972 2009 2012
24. B.M. Trost, and D.C. Lee J. Am. Chem. Soc. 110 1988 6556 6558
25. B. List, R.A. Lerner, and C.F. Barbas J. Am. Chem. Soc. 122 2000 2395 2396
26. T.L. Liu, Z.L. He, H.Y. Tao, Y.P. Cai, and C.J. Wang Chem. Commun. 47 2011 2616 2618
27. B.M. Trost, N. Cramer, and S.M. Silverman J. Am. Chem. Soc. 129 2007 12396 12397
28. S. Chikaoka, A. Toyao, M. Ogasawara, O. Tamura, and H. Ishibashi J. Org. Chem. 68 2003 312 318
29. M. Inui, A. Nakazaki, and S. Kobayashi Org. Lett. 9 2007 469 472
30. F. Gonzalez-Lopez de Turiso, and D.P. Curran Org. Lett. 7 2005 151 154
31. T. Lanza, R. Leardini, M. Minozzi, D. Nanni, P. Spagnolo, and G. Zanardi Angew. Chem. Int. Ed. 47 2008 9439 9442
32. A. Nandakumar, P. Thirumurugan, P.T. Perumal, P. Vembu, M.N. Ponnuswamy, and P. Ramesh Bioorg. Med. Chem. Lett. 20 2010 4252 4258
33. K. Karthikeyan, P.M. Sivakumar, M. Doble, and P.T. Perumal Eur. J. Med. Chem. 45 2010 3446 3452
34. G. Bhaskar, Y. Arun, C. Balachandran, C. Saikumar, and P.T. Perumal Eur. J. Med. Chem. 51 2012 79 91
35. T.H. Babu, P. Sujeet, D. Muralidharan, and P.T. Perumal Synlett 14 2010 2125 2129
36. T.H. Babu, A.J. Abragam, D. Muralidharan, and P.T. Perumal Tetrahedron Lett. 51 2010 994 996
37. T.H. Babu, and P.T. Perumal Synlett 3 2010 341 344
38. Crystallographic Data for Compound 6a in this Paper have been Deposited with the Cambridge Crystallographic Data Centre as Supplemental Publication No. CCDC-972722. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 01223 336033 or email: deposit@ccdc.cam.ac.uk
39. B. Matjaz, P. Andrej, R. Miha, A. Gregor, and T. Dusan J. Med. Chem. 55 2012 6413 6426
40. J.J. Cui, M. Tran-Dube, H. Shen, M. Nambu, P.P. Kung, M. Parish, L. Jia, J. Meng, L. Funk, I. Botrous, M. McTigue, N. Grodsky, K. Ryan, E. Padrique, G. Alton, S. Timofeevski, S. Yamazaki, Q. Li, H. Zou, J. Christensen, B. Mroczhowski, S. Bender, R.S. Kania, and M.P. Edwards J. Med. Chem. 54 2011 6342 6363
41. C.R. Corbeil, C.I. Williams, and P. Labute J. Comput. Aided Mol. Des. 26 2012 775 786
42. R. Ottana, R. Maccari, J. Mortier, A. Caselli, S. Amuso, G. Camici, A. Rotondo, G. Wolber, and P. Paoli Eur. J. Med. Chem. 71 2014 112 127
43. C. Balachandran, V. Duraipandiyan, N.A. Al-Dhabi, K. Balakrishna, N.P. Kalia, V.S. Rajput, I.A. Khan, and S. Ignacimuthu Indian J. Microbiol. 52 2012 676 681
44. C. Balachandran, V. Duraipandiyan, K. Balakrishna, R. Lakshmi Sundaram, A. Vijayakumar, S. Ignacimuthu, and N.A. Al-Dhabi Environ. Chem. Lett. 11 2013 303 308
45. C. Balachandran, V. Duraipandiyan, and S. Ignacimuthu Asian Pac. J. Trop. Biomed. 2012 712 716