Design, synthesis and biological evaluations of chirally pure 1,2,3,4-tertrahydroisoquinoline analogs as anti-cancer agents

European Journal of Medicinal Chemistry

Volumn 92, Issue , 2015, Pages 608-618

  Ramanivas, Triparagiri ^a,b   Sushma, Bottu ^c   Nayak, V Lakshma ^a   Chandra Shekar, Kunta ^a   Srivastava, Ajay Kumar ^a,b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

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

Author keywords

1,2,3,4 Tetrahydroisoquinolines (THIQ); Annexin V FITC assay and apoptosis; Caspase 3; Cell cycle analysis; Tubulin polymerization

Indexed keywords

(4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLIN 2(1H) YL) (2 HYDROXY 4 METHOXYPHENYL) METHANONE; 1 4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDRO ISOQUINOLIN 2(1H) YL 3 (2,3 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDRO ISOQUINOLIN 2(1H) YL 3 (4 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDRO ISOQUINOLIN 2(1H) YL 3 PHENYLPROP 2 EN 1 ONE; 1 4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLIN 2(1H) YL 3 (3 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLIN 2(1H) YL 3 (4 HYDROXY 3 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLIN 2(1H) YL 3 (4 NITROPHENYL)PROP 2 EN 1 ONE; 1 [4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLIN 2(1H) YL]BUT 2 YN 1 ONE; 11 (BENZYLOXY) 2 TOSYL 2,3,11,11A TETRAHYDRO 1H PYRAZINO[1,2 B]ISOQUINOLIN 4(6H) ONE; 11 (BENZYLOXY) 3 METHYL 2 TOSYL 2,3,11,11A TETRAHYDRO 1H PYRAZINO[1,2 B]ISOQUINOLIN 4(6H) ONE; 3 BENZYL 11 (BENZYLOXY) 2 TOSYL 2,3,11,11A TETRAHYDRO 1H PYRAZINO[1,2 B]ISOQUINOLIN 4(6H) ONE; ANTINEOPLASTIC AGENT; CASPASE 3; ETOPOSIDE; N [1 [4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLINE 2(1H) YLL] 1 OXO 3 PHENYLPROPAN 2 YL] 4 METHYLBENZENESULFONAMIDE; N [1 [4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLINE 2(1H) YLL] 1 OXOPROPAN 2 YL] 4 METHYLBENZENESULFONAMIDE; N [1 [4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLINE 2(1H) YLL] 3 METHYL 1 OXYBUTAN 2 YL] 4 METHYLBENZENESULFONAMIDE; N [2 [4 (BENZYLOXY) 3 (HYDROXYMETHYL) 1,2,3,4 TETRAHYDROISOQUINOLINE 2 CARBONYL]PHENYL] 4 METHYLBENZENESULFONAMIDE; N [2 [4 (BENZYLOXY) 3 (HYDROXYMETHYL) 3,4 DIHYDROISOQUINOLINE 2(1H) YLL] 2 OXOETHYL] 4 METHYLBENZENESULFONAMIDE; NOCODAZOLE; PROTEIN BAX; PROTEIN BCL 2; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; ISOQUINOLINE DERIVATIVE;

A549 CELL LINE; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; G2 PHASE CELL CYCLE CHECKPOINT; HELA CELL LINE; HEPG2 CELL LINE; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; MCF 7 CELL LINE; MICROTUBULE ASSEMBLY; PROSTATE CANCER CELL LINE; STRUCTURE ACTIVITY RELATION; TUBULIN POLYMERIZATION ASSAY; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HEP G2 CELLS; HUMANS; ISOQUINOLINES; MCF-7 CELLS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84922266776     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.01.030     Document Type: Article

References (31)

1. J.D. Scott, R.M. Williams, Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics, Chem. Rev. 102 (2002) 1669e1730.
2. K.L. Rinehart, Antitumor compounds from tunicates, Med. Res. Rev. 20 (2000) 1e27.
3. T. Saitoh, K. Abe, M. Ishikawa, M. Nakatani, S. Shimazu, N. Satoh, F. Yoneda, K. Taguchi, Y. Horiguchi, Synthesis and in vitro cytotoxicity of 1,2,3,4-tetrahydroisoquinoline derivatives, Eur. J. Med. Chem. 41 (2006) 241e252.
4. R. Pingaew, P. Mandi, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity, Eur. J. Med. Chem. 81 (2014) 192e203.
5. Y. Zhang, J. Feng, Y. Jia, X. Wang, L. Zhang, C. Liu, H. Fang, W. Xu, Development of tetrahydroisoquinoline-based hydroxamic acid derivatives: potent histone deacetylase inhibitors with marked in vitro and in vivo antitumor activities, J. Med. Chem. 54 (2011) 2823e2838.
6. A. Wasik, E. Mozdzen, I. Romanska, J. Michaluk, L. Antkiewicz-Michaluk, Antidepressant-like activity of the endogenous amine, 1-methyl-1,2,3,4-tetrahydroisoquinoline in the behavioral despair test in the rat, and its neurochemical correlates: a comparison with the classical antidepressant, imipramine, Eur. J. Pharmacol. 700 (2013) 110e117.
7. J.J. Luszczki, L. Antkiewicz-Michaluk, S.J. Czuczwar, Isobolographic analysis of interactions between 1-methyl-1,2,3,4-tetrahydroisoquinoline and four conventional antiepileptic drugs in the mouse maximal electroshock-induced seizure model, Eur. J. Pharmacol. 602 (2009) 298e305.
8. Z. Zhu, J. Furr, J.K. Buolamwin, Synthesis, Flow Cytometric, Evaluation of novel 1,2,3,4-Tetrahydroisoquinoline conformationally constrained analogues of Nitrobenzylmercaptopurine Riboside (NBMPR) designed for probing its conformation when bound to the es nucleoside transporter, J. Med. Chem. 46 (2003) 831e837.
9. D. Dou, P. Viwanathan, Y. Li, G. He, K.R. Alliston, G.H. Lushington, J.D. Brown-Clay, R. Padmanabhan, W.C. Groutas, Design, Synthesis, and in vitro evaluation of potential West Nile Virus protease inhibitors based on the 1-Oxo-1,2,3,4-tetrahydroisoquinoline and 1-oxo-1,2-dihydroisoquinoline Scaffolds, J. Comb. Chem. 12 (2010) 836e843.
10. X. Fang, Y. Yin, Y.T. Chen, L. Yao, B. Wang, M.D. Cameron, L. Lin, S. Khan, C. Ruiz, T. Schroter, W. Grant, A. Weiser, J. Pocas, A. Pachori, S. Schürer, P. LoGrasso, Y. Feng, Tetrahydroisoquinoline derivatives as highly selective and potent Rho kinase inhibitors, J. Med. Chem. 53 (2010) 5727e5737.
11. R. Pingaew, A. Worachartcheewan, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Synthesis, cytotoxicity and QSAR study of N-tosyl-1,2,3,4-tetrahydroisoquinoline derivatives, Arch. Pharm. Res. 36 (2013) 1066e1077.
12. H. Hatano, F. Takekawa, K. Hashimoto, M. Ishihara, M. Kawase, C. Qing, W. Qin-Tao, H. Sakagami, Tumor-specific cytotoxic activity of 1,2,3,4-Tetrahydroisoquinoline derivatives against human oral squamous cell carcinoma cell lines, Anticancer Res. 29 (2009) 3079e3086.
13. A.K. Srivastava, M. Koh, S.B. Park, A synthetic route to highly substituted 1,2,3,4-tetrahydroisoquinolines via Yb(OTf)3-catalyzed diastereoselective ring opening of bridged oxazolidines: asymmetric synthesis of 2-Azapodophyllotoxin, Chem. Eur. J. 17 (2011) 4905e4913.
14. D. Ghosh, D. Sahu, S. Saravanan, S.H.R. Abdi, B. Ganguly, N.-U.H. Khan, R.I. Kureshy, H.C. Bajaj, Synthetically amenable amide derivatives of tosylatedamino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity, Org. Biomol. Chem. 11 (2013) 3451e3460.
15. M. Botta, S. Armaroli, D. Castagnolo, G. Fontana, P. Perad, E. Bombardelli, Synthesis and biological evaluation of new taxoids derived from 2-deacetoxytaxinine J, Bioorg. Med. Chem. Lett. 17 (2007) 1579.
16. M. Blank, Y. Shiloh, Programs for cell death: apoptosis is only one way to go, Cell. Cycle 6 (2007) 686e695.
17. K. Samanta, B. Chakravarti, J.K. Mishra, S.K.D. Dwivedi, V.L. Nayak, P. Choudhry, H.K. Bid, R. Konwar, N. Chattopadhyay, G. Panda, Anti-tumor activity of a new series of benzoxazepine derivatives in breast cancer, Bioorg. Med. Chem. Lett. 20 (2010) 283e287.
18. 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, Cucurbitacin B induces apoptosis and S phase cell cycle arrest in BEL-7402 human hepatocellular carcinoma cells and is effective via oral administration, Cancer Lett. 294 (2010) 118e124.
19. C. Kanthou, O. Greco, A. Stratford, I. Cook, R. Knight, O. Benzakour, G. Tozer, The tubulin-binding agent combretastatin a-4-phosphate arrests endothelial cells in mitosis and induces mitotic cell death, Am. J. Pathol. 165 (2004) 1401e1411.
20. K. Huber, P. Patel, L. Zhang, H. Evans, A.D. Westwell, P.M. Fischer, S. Chan, S. Martin, 2-[(1-Methylpropyl)dithio]-1H-imidazole inhibits tubulin polymerization through cysteine oxidation, Mol. Cancer Ther. 7 (2008) 143e151.
21. A. Kamal, Y.V.V. Srikanth, T.B. Shaik, M.N.A. Khan, M. Ashraf, M.K. Reddy, K.A. Kumar, S.V. Kalivendi, 2-Anilinonicotinyl linked 1,3,4-oxadiazole derivatives: synthesis, antitumour activity and inhibition of tubulin polymerization, Med. Chem. Commun. 2 (2011) 819e823.
22. S.M. Konstantinov, M.R. Berger, Human urinary bladder carcinoma cell lines respond to treatment with alkylphosphocholines, Cancer Lett. 144 (1999) 153e160.
23. P.M. Henkels, J.J. Turchi, Cisplatin-induced apoptosis proceeds by caspase-3-dependent and-independent pathways in cisplatin-resistant and-sensitive human ovarian Cancer cell lines, Cancer Res. 59 (1999) 3077e3083.
24. L.H. Zhang, L. Wu, H.K. Raymon, R.S. Chen, L. Corral, M.A. Shirley, R.K. Narla, J. Gamez, G.W. Muller, D.I. Stirling, B.J. Bartlett, P.H. Schafer, F. Payvandi, The synthetic compound CC-5079 is a potent inhibitor of tubulin polymerization and tumor necrosis factor-a Production with antitumor activity, Cancer Res. 66 (2006) 951e959.
25. N.M. Weir, K. Selvendiran, V.K. Kutala, L. Tong, S. Vishwanath, M. Rajaram, S. Tridandapani, S. Anant, P. Kuppusamy, Curcumin induces G2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by modulating akt and p38 mAPK, Cancer Biol. Ther. 6 (2007) 178e184.
26. S. Iyer, D.J. Chaplin, D.S. Rosenthal, A.M. Boulares, L. Li, M.E. Smulson, Induction of apoptosis in proliferating human endothelial cells by the tumorspecific antiangiogenesis agent combretastatin A-4, Cancer Res. 58 (1998) 4510e4514.
27. H. Zhu, J. Zhang, N. Xue, Y. Hu, B. Yang, Q. He, Novel combretastatin A-4 derivative XN0502 induces cell cycle arrest and apoptosis in A549 cells, Invest New. Drugs 28 (2010) 493e501.
28. J.E. Chipuk, T. Moldoveanu, F. Llambi, M.J. Parsons, D.R. Green, The BCL-2 family reunion, Mol. Cell 37 (2010) 299e310.
29. M. Szumilak, A. Szulawska-Mroczek, K. Koprowska, M. Stasiak, W. Lewgowd, A. Stanczak, M. Czyz, Synthesis and in vitro biological evaluation of new polyamine conjugates as potential anticancer drugs, Eur. J. Med. Chem. 45 (2010) 5744e5751.
30. G. Shafi, A. Munshi, T.N. Hasan, A.A. Alshatwi, A. Jyothy, D.K.Y. Lei, Induction of apoptosis in HeLa cells by chloroform fraction of seed extracts of Nigella sativa, Cancer Cell. Int. 9 (2009) 1475e2867.
31. L.J. Browne, C. Gude, H. Rodriguez, R.E. Steele, A.J. Bhatnager, Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease, J. Med. Chem. 34 (1991) 725e736.