H2O-mediated isatin spiro -epoxide ring opening with NaCN: Synthesis of novel 3-tetrazolylmethyl-3-hydroxy-oxindole hybrids and their anticancer evaluation

European Journal of Medicinal Chemistry

Volumn 104, Issue , 2015, Pages 11-24

  Sharma, Pankaj ^a   Senwar, Kishna Ram ^a   Jeengar, Manish Kumar ^a   Reddy, T Srinivasa ^b   Naidu, V G M ^a   Kamal, Ahmed ^b   Shankaraiah, Nagula ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

3 Hydroxy oxindole; Anticancer; Apoptosis; Azide nitrile cycloaddition; Isatin epoxide; Tetrazoles

Indexed keywords

3 [(1H TETRAZOL 5 YL)METHYL] 1 (4 BROMOBENZYL) 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 1 (4 BROMOBENZYL) 5 CHLORO 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 1 (4 BROMOBENZYL) 5 FLUORO 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 1 BENZYL 3 HYDROXY 5 METHYLINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 1 BENZYL 5 CHLORO 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 1 BENZYL 5 FLUORO 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 1 ETHYL 3 HYDROXY 5 METHYLINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 1 ETHYL 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 3 HYDROXY 1,5 DIMETHYLINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 5 BROMO 1 (4 BROMOBENZYL) 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 5 BROMO 1 ETHYL 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 5 BROMO 3 HYDROXY 1 METHYLINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 5 CHLORO 1 ETHYL 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 5 CHLORO 3 HYDROXY 1 METHYLINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL] 5 FLUORO 3 HYDROXY 1 METHYLINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL]1 BENZYL 3 HYDROXYINDOLIN 2 ONE; 3 [(1H TETRAZOL 5 YL)METHYL]1 BENZYL 5 BROMO 3 HYDROXYINDOLIN 2 ONE; 4',6 DIAMIDINO 2 PHENYLINDOLE; ACRIDINE ORANGE; ANTINEOPLASTIC AGENT; EPOXIDE; ETHIDIUM BROMIDE; INDOLE DERIVATIVE; ISATIN DERIVATIVE; LIPOCORTIN 5; REACTIVE OXYGEN METABOLITE; SODIUM CYANIDE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; WATER; 3-TETRAZOLYLMETHYL-3-HYDROXY-OXINDOLE; ISATIN; SPIRO COMPOUND;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BINDING ASSAY; BREAST CANCER CELL LINE; CELL PROLIFERATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLOADDITION; DNA FRAGMENTATION ASSAY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; FEMALE; G2 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; HYBRID; IC50; IN VITRO STUDY; MALE; MITOCHONDRIAL MEMBRANE POTENTIAL; OVARIAN CANCER CELL LINE; PROSTATE CANCER CELL LINE; PROSTATE EPITHELIUM CELL; RING OPENING; STAINING; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; EPOXY COMPOUNDS; HUMANS; INDOLES; ISATIN; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; SODIUM CYANIDE; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAZOLES; WATER;

EID: 84942590646     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.09.025     Document Type: Article

References (86)

1. J. Baselga, S.M. Swain, Nat. Rev. Cancer 9 (2009) 463-475.
2. C.H.J. Brown, S. Lain, C.H.S. Verma, A.R. Fersht, D.P. Lane, Nat. Rev. Cancer 9 (2009) 862-873.
3. S. Peddibhotla, Curr. Bioact. Compd. 5 (2009) 20-38 and references cited herein.
4. C.V. Galliford, K.A. Scheidt, Angew. Chem. Int. Ed. 46 (2007) 8748-8758.
5. C. Marti, E.M. Carreira, Eur. J. Org. Chem. (2003) 2209-2219.
6. T. Ueda, M. Inada, I. Okamoto, N. Morita, O. Tamura, Org. Lett. 10 (2008) 2043-2046.
7. T. Itoh, H. Ishikawa, Y. Hayashi, Org. Lett. 11 (2009) 3854-3857.
8. S. Lin, Z. Yang, B.H.B. Kwok, M. Koldobskiy, C.M. Crews, J. Am. Chem. Soc. 126 (2004) 6347-6355.
9. H.B. Rasmussen, J.K. Macleod, J. Nat. Prod. 60 (1997) 1152-1154.
10. H.V. Erkizan, Y. Kong, M. Merchant, S. Schlottmann, J.S. Barber-Rotenberg, L. Yuan, O.D. Abaan, T. Chou, S. Dakshanamurthy, M.L. Brown, A. Uren, J.A. Toretsky, Nat. Med. 15 (2009) 750-756.
11. V.U. Khuzhaev, I. Zhalolov, K.K. Turgunov, B. Tashkhodzhaev, M.G. Levkovich, S.F. Arpova, A.S. Shashkov, Chem. Nat. Compd. 40 (2004) 269-272.
12. J.I. Jimenez, U. Huber, R.E. Moore, G.M.L. Patterson, J. Nat. Prod. 62 (1999) 569-572.
13. J.S. Carle, C. Christophersen, J. Org. Chem. 46 (1981) 3440-3443.
14. M.J. Moon, S.K. Lee, J.W. Lee, W.K. Song, S.W. Kim, J.I. Kim, C. Cho, S.J. Choi, Y.C. Kim, Bioorg. Med. Chem. 14 (2006) 237-246.
15. A. Gursoy, N. Karali, Eur. J. Med. Chem. 38 (2003) 633-643.
16. P. Singh, P. Sharma, A. Anand, P.M.S. Bedi, T. Kaur, A.K. Saxena, V. Kumar, Eur. J. Med. Chem. 55 (2012) 455-461.
17. J. Ma, S. Li, K. Reed, P. Guo, J.M. Gallo, J. Pharmacol. Exp. Ther. 305 (2003) 833-839.
18. M.E. Lane, B. Yu, A. Rice, K.E. Lipson, C. Liang, L. Sun, C. Tang, G. McMahon, R.G. Pestell, S.A. Wadler, Cancer Res. 61 (2001) 6170-6177.
19. H. Prenen, J. Cools, N. Mentens, C. Folens, R. Sciot, P. Schoffski, A. Van Oosterom, P. Marynen, M. Debiec-Rychter, Clin. Cancer Res. 8 (2006) 2622-2627.
20. R.J. Motzer, M.D. Michaelson, B.G. Redman, G.R. Hudes, G. Wilding, R.A. Figlin, M.S. Ginsberg, S.T. Kim, C.M. Baum, S.E. DePrimo, J.Z. Li, C.L. Bello, C.P. Theuer, D.J. George, B.I. Rini, J. Clin. Oncol. 24 (2006) 16-24.
21. R.J. Roskoski, Biochem. Biophys. Res. Commun. 356 (2007) 323-328.
22. N.R. Penthala, T.R. Yerramreddy, N.R. Madadi, P.A. Crooks, Bioorg. Med. Chem. Lett. 20 (2010) 4468-4471.
23. M.D. Hall, N.K. Salam, J.L. Hellawell, H.M. Fales, C.B. Kensler, J.A. Ludwig, G. Szakacs, D.E. Hibbs, M.M. Gottesman, J. Med. Chem. 52 (2009) 3191-3204.
24. D. Havrylyuk, N. Kovach, B. Zimenkovsky, O. Vasylenko, R. Lesyk, Arch. Pharm. Chem. Life Sci. 344 (2011) 514-522.
25. K. Kumar, S. Sagar, L. Esau, M. Kaur, V. Kumar, Eur. J. Med. Chem. 58 (2012) 153-159
26. J.R. Chen, X.P. Liu, X.Y. Zhu, L. Li, Y.F. Qiao, J.M. Zhang, W.J. Xiao, Tetrahedron 63 (2007) 10437-10444.
27. M. Raj, N. Veerasamy, V.K. Singh, Tetrahedron Lett. 51 (2010) 2157-2159.
28. Q.S. Guo, M. Bhanushali, C.G. Zhao, Angew. Chem. Int. Ed. 49 (2010) 9460-9464.
29. C. Cassani, P. Melchiorre, Org. Lett. 14 (2012) 5590-5593.
30. S. Allu, N. Molleti, R. Panem, V.K. Singh, Tetrahedron Lett. 52 (2011) 4080-4083.
31. M. Kinsella, P.G. Duggan, C.M. Lennon, Tetrahedron Asymmetry 22 (2011) 1423-1429.
32. V. Bavetsias, J.H. Marriott, C. Melin, R. Kimbell, Z.S. Matusiak, F.T. Boyle, A.L. Jackman, J. Med. Chem. 43 (2000) 1910-1926
33. R.S. Upadhayaya, S. Jain, N. Sinha, N. Kishore, R. Chandra, S.K. Arora, Eur. J. Med. Chem. 39 (2004) 579-592.
34. V.A. Ostrovskii, R.E. Trifonov, E.A. Popova, Russ. Chem. Bull. 61 (2012) 768-780.
35. H. Gao, J.M. Shreeve, Chem. Rev. 111 (2011) 7377-7436 and references cited herein.
36. E.A. Popova, R.E. Trifonov, V.A. Ostrovskii, ARKIVOC (2012) 45-56.
37. G. Arom, L.A. Barrios, O. Roubeau, P. Gamez, Coord. Chem. Rev. 255 (2011) 485-546.
38. B. Maji, H. Yamamoto, Angew. Chem. Int. Ed. 53 (2014) 8714-8717.
39. M. Limbach, Chem. Biodiversity (2006) 119-133.
40. A.G. Doyle, E.N. Jacobsen, Chem. Rev. 107 (2007) 5713-5743.
41. C. Najera, J.M. Sansano, Chem. Rev. 107 (2007) 4584-4671.
42. M. Bhanushali, C.G. Zhao, Synthesis (2011) 1815-1819.
43. Y. Mirabal-Gallardo, J. Pierola, N. Shankaraiah, L.S. Santos, Tetrahedron Lett. 53 (2012) 3672-3675.
44. L.V. Myznikov, A. Hrabalek, G.I. Koldobskii, Chem. Heterocycl. Compd. 43 (2007) 1-9.
45. M.L. Barreca, S. Ferro, A. Rao, L.D. Luca, M. Zappala, A.M. Monforte, Z. Debyser, M. Witvrouw, A. Chimirri, J. Med. Chem. 48 (2005) 7084-7088.
46. X. Li, R. Vince, Bioorg. Med. Chem. 14 (2006) 5742-5755.
47. B. Schmidt, B. Schieffcr, J. Med. Chem. 46 (2003) 2261-2270.
48. R.A. Powers, B.K. Shoichet, J. Med. Chem. 45 (2002) 3222-3234.
49. O.K. Andersson, S. Neldam, Blood Pressure 7 (1998) 53-59.
50. Selected references related to azide-nitrile cycloaddition: B. Das, C.R. Reddy, D.N. Kumar, M. Krishnaiah, R. Narender, Synlett (2010) 391-394.
51. D. Cantillo, B. Gutmann, C.O. Kappe, J. Am. Chem. Soc. 133 (2011) 4465-4475.
52. S.D. Gawande, M.J. Raihan, M.R. Zanwar, V. Kavala, D. Janreddy, C. Kuo, M. Chen, T. Kuo, C. Yao, Tetrahedron 69 (2013) 1841-1848.
53. T. Jin, F. Kitahara, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 49 (2008) 2824-2827.
54. B. Akhlaghinia, S. Rezazadeh, J. Br. Chem. Soc. 23 (2012) 2197-2203.
55. L. Bosch, J. Vilarrasa, Angew. Chem. Int. Ed. 46 (2007) 3926-3930.
56. M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50 (2009) 4435-4438.
57. S. Kumar, S. Dubey, N. Saxena, S.K. Awasthi, Tetrahedron Lett. 55 (2014) 6034-6038.
58. N. Nowrouzi, S. Farahi, M. Irajzadeh, Tetrahedron Lett. 56 (2015) 739-743.
59. Z.P. Demko, K.B. Sharpless, Org. Lett. 4 (2002) 2525-2527.
60. Z.P. Demko, K.B. Sharpless, J. Org. Chem. 66 (2001) 7945-7950.
61. N. Shankaraiah, K.P. Siraj, S. Nekkanti, V. Srinivasulu, M. Satish, P. Sharma, K.R. Senwar, M.V.P.S. Vishnuvardhan, S. Ramakrishna, A. Kamal, Bioorg. Chem. 59 (2015) 130-139.
62. N. Shankaraiah, S. Nekkanti, K.J. Chudasama, K.R. Senwar, P. Sharma, M.K. Jeengar, V.G.M. Naidu, V. Srinivasulu, A. Kamal, Bioorg. Med. Chem. Lett. 24 (2014) 5413-5416.
63. A. Kamal, S. Prabhakar, M.J. Ramaiah, P.V. Reddy, Ch.R. Reddy, A. Mallareddy, N. Shankaraiah, T.L.N. Reddy, S.N.C.V.L. Pushpavalli, M.P. Bhadra, Eur. J. Med. Chem. 46 (2011) 3820-3831.
64. K.R. Senwar, P. Sharma, S. Nekkanti, M. Sathish, A. Kamal, B. Sridhar, N. Shankaraiah, New. J. Chem. 39 (2015) 3973-3981.
65. K.R. Senwar, P. Sharma, T.S. Reddy, M.K. Jeengar, V.L. Nayak, V.G.M. Naidu, A. Kamal, N. Shankaraiah, Eur. J. Med. Chem. 102 (2015) 413-424.
66. A. Kamal, N. Shankaraiah, Ch. R. Reddy, S. Prabhakar, N. Markandeya, H.K. Srivastava, G.N. Sastry, Tetrahedron 66 (2010) 5498-5506.
67. A. Kamal, K. Sreekanth, P.P. Kumar, N. Shankaraiah, G. Balakishan, M.J. Ramaiah, S.N.C.V.L. Pushpavalli, P. Ray, M.P. Bhadra, Eur. J. Med. Chem. 45 (2010) 2173-2181.
68. A. Kamal, N. Shankaraiah, V. Devaiah, K.L. Reddy, A. Juvekar, S. Sen, N. Kurian, S. Zingde, Bioorg. Med. Chem. Lett. 18 (2008) 1468-1473.
69. T. Sandmeyer, Helv. Chim. Acta 2 (1919) 234-242.
70. M. Chouhan, K.R. Senwar, R. Sharma, V. Grover, V.A. Nair, Green Chem. 13 (2011) 2553-2560.
71. E.J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 87 (1965) 1353-1364.
72. S. Shrivastava, P. Kulkarni, D. Thummuri, M.K. Jeengar, V.G.M. Naidu, M. Alvala, G.B. Reddy, S. Ramakrishna, Apoptosis 19 (2014) 1148-1164.
73. X.J. Song, Y. Shao, X.G. Dong, Chin. Chem. Lett. 22 (2011) 1036-1038.
74. N.A. Franken, H.M. Rodermond, J. Stap, J. Haveman, C.V. Bree, Nat. Protoc. 1 (2006) 2315-2319.
75. U.V. Mallavadhani, N.R. Vanga, M.K. Jeengar, V.G.M. Naidu, Eur. J. Med. Chem. 74 (2014) 398-404.
76. S. Shrivastava, M.K. Jeengar, V.S. Reddy, G.B. Reddy, V.G.M. Naidu, Exp. Mol. Pathol. 98 (2015) 313-327.
77. S.M. Konstantinov, M.R. Berger, Cancer Lett. 144 (1999) 153-160.
78. P.M. Henkels, J.J. Turchi, Cancer Res. 59 (1999) 3077-3083.
79. K.T. Chan, F.Y. Meng, Q. Li, C.Y. Ho, T.S. Lam, Y. To, W.H. Lee, M. Li, K.H. Chu, M. Toh, Cancer Lett. 294 (2010) 118-124.
80. J.K. Shen, H.P. Du, M. Yang, Y.G. Wang, J. Jin, Ann. Hematol. 88 (2009) 743-752.
81. R. Swami, I. Singh, M.K. Jeengar, V.G.M. Naidu, W. Khan, R. Sistla, Int. J. Pharm. 486 (2015) 287-296.
82. L.J. Browne, C. Gude, H. Rodriguez, R.E. Steele, A. Bhatnager, J. Med. Chem. 34 (1991) 725-736.
83. A. Kamal, T.S. Reddy, M.V.P.S. Vishnuvardhan, V.D. Nimbarte, A.V. Subba Rao, V. Srinivasulu, N. Shankaraiah, Bioorg. Med. Chem. 23 (2015) 4608-4623.
84. D. Trachootham, J. Alexandre, P. Huang, Nat. Rev. Drug Discov. 8 (2009) 579-590
85. T.S. Reddy, H. Kulhari, V.G. Reddy, V. Bansal, A. Kamal, R. Shukla, Eur. J. Med. Chem. 101 (2015) 790-805.
86. G.W. Wang, A.X. Zhou, J.J. Wang, R.B. Hu, S.D. Yang, Org. Lett. 15 (2013) 5270-5273.