Silyl modification of biologically active compounds. 13. Synthesis, cytotoxicity and antibacterial action of N-methyl-N-(2-triorganylsiloxyethyl)-1, 2,3,4-tetrahydro(iso)quinolinium iodides

Applied Organometallic Chemistry

Volumn 27, Issue 2, 2013, Pages 114-124

  Zablotskaya, Alla ^a   Segal, Izolda ^a   Popelis, Yuris ^a   Grinberga, Solveiga ^a   Shestakova, Irina ^a   Nikolajeva, Vizma ^b   Eze, Daina ^b  

^a LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

^b UNIVERSITY OF LATVIA   (Latvia)

Author keywords

antimicrobial activity; antitumour activity; choline; drug research; silicon; silylation; tetrahydro(iso)quinoline

Indexed keywords

ANTI-MICROBIAL ACTIVITY; ANTITUMOUR ACTIVITY; CHOLINE; DRUG RESEARCH; SILYLATIONS; TETRAHYDRO(ISO)QUINOLINE;

AROMATIC COMPOUNDS; CELL CULTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILICON; SYNTHESIS (CHEMICAL);

BIOACTIVITY;

EID: 84872679440     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.2952     Document Type: Article

References (38)

1. A. M. van Hattum, H. M. Pinedo, H. M. M. Schluper, F. N. Hausheer, E. Boven, Int. J. Cancer 2000, 88, 260.
2. A. K. Bence, C. A. Mattingly, T. G. Burke, V. R. Adams, Cancer Chemother. Pharmacol. 2004, 54, 354.
3. W. K. Anderson, R. Kasliwal, D. M. Houston, Y.-S. Wang, V. L. Narayanan, R. D. Haugwitz, J. Plowman, J. Med. Chem. 1995, 38, 3789.
4. M.-C. Bonache, C. Chamorro, S. Velazquez, E. de Clercq, J. Balzarini, F. Rodriquez-Barrios, F. Gago, M.-J. Camarasa, A. San-Felix, J. Med. Chem. 2005, 48, 6653.
5. M. D. Mashkovsky, Drugs (12th edn), Medicina, Moscow, 1993.
6. W. Bains, R. Tacke, Curr. Opin. Drug Discovery Dev. 2003, 6, 526.
7. D. Schirlin, J. N. Collard, J. M. Hornspreger, P. R. Keshary, Acetylcholinesterase inhibitors. Merrel Pharmaceuticals, US-05693668, 1997.
8. F. H. Hausheer, K. Haridas, P. Seetharamulu, D. G. Reddy, S. Yao, P. N. Petluru, M. Dhanabalan, Highly lipophilic camptothecin derivatives. Bionumeric Pharmaceuticals, WO-09835940, 1998.
9. D. P. Curran, H. Josien, D. Bom, T. G. Burke, Camptotecin analogs and methods of preparation thereof. University of Pittsburgh, WO-0035924, 2000.
10. S. Farkas, S. Foldeak, E. Karpati, P. Hegyes, J. Kreidl, L. Szporny, L. Czibula, S. Petofi Vassne, Organosilicon derivatives, pharmaceutical compositions containing them and process of preparing same. Richter Gedeon Vegyeszeti Gyar RT, EP-00468825 (1992).
11. J. S. Millership, M. L. Shanks, Int. J. Pharm. 1986, 28, 1-9.
12. E. Lukevics, A. Zablotskaya, Metalloorg. Khim. 1993, 6, 263.
13. V. V. Belakhov, Y. D. Shenin, Pharm. Chem. J. 2008, 42, 322.
14. M. A. Peterson, M. Oliveira, M. A. Christiansen, C. E. Cutler, Bioorg. Med. Chem. Lett. 2009, 19, 6775.
15. J. R. Shelton, S. R. Burt, M. A. Peterson, Bioorg. Med. Chem. Lett. 2011, 21, 1484.
16. O. J. Donadel, T. Martin, V. S. Martin, J. Villar, J. M. Padron, Bioorg. Med. Chem. Lett. 2005, 15, 3536.
17. C. Nguyen, G. F. Ruda, A. Schipani, G. Kasinathan, I. Leal, A. Musso-Buendia, M. Kaiser, R. Brun, L. M. Ruiz-Perez, B.-L. Sahlberg, N. G. Johansson, J. Med. Chem. 2006, 49, 4183.
18. E. Lukevics, I. Segal, I. Birgele, A. Zablotskaya, Chem. Heterocycl. Compd. 1998, 34, 1076.
19. A. Zablotskaya, I. Segal, S. Germane, I. Shestakova, I. Domracheva, A. Nesterova, A. Geronikaki, E. Lukevics, Chem. Heterocycl. Compd. 2002, 38, 859.
20. A. Zablotskaya, I. Segal, Yu. Popelis, E. Lukevics, S. Baluja, I. Shestakova, I. Domracheva, Appl. Organomet. Chem. 2006, 20, 721.
21. M. Lemort, L. S. Chao, M. Radermecker, R. Demeure, MAGNETOM Flesh 2007, 38.
22. J. M. Sanz, R. Lopez, J. L. Garcia, FEBS Lett. 1988, 232, 308.
23. G. W. A. Milne, (Ed), Ashgate Handbook of Antineoplastic Agents, Gower Publishing, Aldershot, UK, 2000.
24. H. Malonne, G. Atassi, Anticancer Drugs 1997, 8, 811.
25. J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1668.
26. Y. Mikami, K. Yokoyama, H. Tabeta, K. Nakagaki, T. Arai, J. Pharm. Dyn. 1981, 4, 282.
27. G. R. Pettit, V. Gaddamidi, D. L. Herald, S. B. Singh, G. M. Cragg, J. M. Schmidt, F. E. Boettner, M. Williams, Y. Sagawa, J. Nat. Prod. 1986, 49, 995.
28. E. Izbicka, R. Lawrence, E. Raymond, G. Eckhardt, G. Faircloth, J. Jimeno, G. Clark, D. D. Von Hoff, Ann. Oncol. 1998, 9, 981.
29. A. Kleeman, J. Engel, B. Kutscher, D. Reichert,. Pharmaceutical Substances (4th edn), Thieme, New York, 2001.
30. H. R. Lin, M. K. Safo, D. J. Abraham, Bioorg. Med. Chem. Lett. 2007, 17, 2581.
31. C. M. Tarby, R. F. Kaltenbach III, T. Huynh, A. Pudzianowski, H. Shen, M. Ortega-Nanos, S. Sheriff, J. A. Newitt, P. A. McDonnell, N. Burford, C. R. Fairchild, W. Vaccaro, Z. Chen, R. M. Borzilleri, J. Naglich, L. J. Lombardo, M. Gottardis, G. L. Trainor, D. L. Roussell, Bioorg. Med. Chem. Lett. 2006, 16, 2095.
32. C. Jiang, Q. You, F. Liu, W. Wu, Q. Guo, J. Chern, L. Yang, M. Chen, Chem. Pharm. Bull. 2009, 57, 567.
33. A. Zablotskaya, I. Segal, E. Lukevics, S. Belyakov, H. Spies, Appl. Organomet. Chem. 2007, 21, 288.
34. I. Segal, A. Zablotskaya, E. Lukevics, Chem. Heterocycl. Comp. 2005, 41, 613.
35. P. J. Freshney, Culture of Animal Cells: A Manual of Basic Technique, Wiley-Liss, New York, 1994, pp. 296.
36. D. J. Fast, R. C. Lynch, R. W. Leu, J. Leukocyte Biol. 1992, 52, 255.
37. A. Wanger, in Antimicrobial Susceptibility Testing Protocols, (Eds:, R. Schwalbe, L. Steele-Moore, A. C. Goodwin,), CRC Press, Boca Raton, FL, 2007, p. 53.
38. C. Eaborn, Organosilicon Compounds, Butterworths, London, 1960, pp. 89.