Skip to main content
SpringerLink
Log in

Synthesis and Cytotoxicity of 3-(Hetarylthio)-1-propynyl(trimethyl)silanes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have developed a two-step method for synthesis of 3-(hetarylthio)-1-propynyl(trimethyl)silanes from thiols in a phase-transfer catalysis system HCCCH2Br-solid K2CO3-18-crown-6-toluene followed by reaction with n-BuLi-Me3SiCl in ether or THF. We have observed that 3-[1,3-bis(trimethylsilyl)-2-propynyl]thioindole displays high cytotoxicity in HT-1080 and MG-22A tumor cell lines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. E. Abele, K. Rubina, R. Abele, I. Sleiksha, and E. Lukevics, Khim. Geterotsikl. Soedin., 1197 (1999).

  2. F. P. Invidiata, S. Grimaudo, P. Giammanco, and L. Giammanco, Farmco, 46, 1489 (1991); Chem. Abstr. 116:187514 (1992).

    Google Scholar 

  3. Varvaresou, A. Papadaki-Valiraki, and Th. Siatra-Papastaikoudi, Bioorg. Med. Chem. Lett., 6, 861 (1996).

    Google Scholar 

  4. K. Tomita, K. Chiba, S. Kashimoto, K. Shibamori, and Y. Tsuzuki, PCT Int. Appl. WO Pat. 9534559; Chem. Abstr. 124:289559 (1996).

    Google Scholar 

  5. M. Gielen, A. Bouhdid, E. R. T. Tiekink, D. de Vos, and R. Willem, Metal Based Drugs, 3, 75 (1996).

    Google Scholar 

  6. A. Gangjee, Yu. Zhu, and S. F. Queener, J. Med. Chem., 41, 4533 (1998).

    Google Scholar 

  7. A. P. Krapcho, S. N. Haydar, S. Truong-Chiott, M. P. Hacker, E. Menta, and G. Beggiolin, Bioorg. Med. Chem. Lett., 10, 305 (2000).

    Google Scholar 

  8. J. P. Dumas, T. K. Joe, H. C. E. Kluender, W. Lee, D. Nagarathnam, R. N. Sibley, N. Su, S. J. Boyer, and J. A. Dixon, PCT Int. Appl. WO Pat. 0123375; Chem. Abstr. 134:266326 (2001).

  9. Y. Tsuzuki, K. Chiba, and K. Hino, Tetrahedron: Assym., 12, 1793 (2001).

    Google Scholar 

  10. W. O. Foye, S. H. An, and T. J. Maher, J. Pharm. Sci., 73, 1168 (1984).

    Google Scholar 

  11. D. T. Chu, J. J. Plattner, L. Klein, and L. L. Shen, Eur. Pat. 424802; Chem. Abstr. 115:136090 (1991).

    Google Scholar 

  12. Y. Ito, H. Kato, S. Yasuda, N. Yagi, T. Yoshida, and T. Suzuki, Jpn. Pat. 04117388; Chem. Abstr. 117:111597 (1992).

    Google Scholar 

  13. Y. Ito, H. Kato, S. Yasuda, T. Yoshida, Y. Yamamoto, and M. Ueshima, Jpn. Pat. 0570467; Chem. Abstr. 119:139203 (1993).

    Google Scholar 

  14. Y. Ito, H. Kato, S. Yasuda, T. Yoshida, and Y. Yamamoto, Jpn. Pat. 04356491; Chem. Abstr. 119:95504 (1993).

    Google Scholar 

  15. Y. H. Choi, A. Park, F. J. Schmitz, and I. van Altena, J. Natur. Prod., 56, 1431 (1993).

    Google Scholar 

  16. M. Flores, A. Fracesch, P. Gallego, J. L. Chicharro, M. Zarzuelo, C. Fernandez, and I. Manzanares, PCT Int. Appl. WO Pat. 0177115; Chem. Abstr. 135:304055 (2001).

    Google Scholar 

  17. K. W. Bair, Canad. Pat. 2012626; Chem. Abstr. 117:26549 (1992).

  18. J. H. Van Maarseveen, P. H. H. Hermkens, E. De Clercq, J. Balzarini, H. W. Scheeren, and C. G. Kruse, J. Med. Chem., 35, 3223 (1992).

    Google Scholar 

  19. J. J. Bhatt, B. R. Shah, H. P. Shah, P. B. Trivedi, N. K. Undavia, and N. C. Desai, Indian J. Chem., 33B, 189 (1994).

    Google Scholar 

  20. S. Ikeda, U. Kimura, T. Ashizawa, K. Gomi, H. Saito, M. Kasai, J. Kanazawa, K. Sasaki, E. Nukui, M. Okabe, and S. Sato, US Pat. 5952355; Chem. Abstr. 131:2286546 (1999).

  21. C. Chin, R. L. Tolman, M. Q. Nguyen, and R. Holcomb, PCT Int. Appl. WO Pat. 0102394; Chem. Abstr. 134:86237 (2001).

    Google Scholar 

  22. R. C. Schnur, R. J. Gallaschun, D. H. Singleton, M. Grissom, D. E. Sloan, P. Goodwin, P. A. McNiff, A. F. J. Fliri, and F. M. Mangano, J. Med. Chem., 34, 1975 (1991).

    Google Scholar 

  23. E.-S. A. Ibrahim, A.-M. M. E. Omar, and M. A. Khalil, J. Pharm. Sci., 69, 1348 (1980).

    Google Scholar 

  24. J. Okada, K. Nakano, H. Miyake, and S. Yasufuku, Chem. Pharm. Bull., 30, 91 (1982).

    Google Scholar 

  25. K. Tsujihara, N. Harada, M. Oohashi, T. Kashida, and K. Oda, Jpn. Pat. 05194517; Chem. Abstr. 120:164209 (1994).

    Google Scholar 

  26. E. Lukevics and L. Ignatovich, Appl. Organometal. Chem., 6, 113 (1992).

    Google Scholar 

  27. K. Rubina, E. Abele, P. Arsenyan, R. Abele, M. Veveris, and E. Lukevics, Metal Based Drugs, 8, 85 (2001).

    Google Scholar 

  28. Kh. Filipova, Yu. L. Frolov, G. S. Liashenko, V. B. Modonov, N. A. Ivanova, I. D. Khalikhman, M. G. Voronkov, and N. S. Vyazankin, Izv. Akad. Nauk SSSR, Ser. Khim., 1847 (1986).

  29. J. B. Baudin, S. A. Julia, and R. Lorne, Bull. Soc. Chim. France, 440 (1992).

  30. R. L. N. Harris, Org. Synth., 53, 1834 (1973).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV-1006

    R. Abele, E. Abele, K. Rubina, O. Dzenitis, P. Arsenyan, I. Shestakova, A. Nesterova, I. Domracheva, J. Popelis, S. Grinberga & E. Lukevics

Authors
  1. R. Abele
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. Abele
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Rubina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. Dzenitis
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. P. Arsenyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. Shestakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. Nesterova
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. I. Domracheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. J. Popelis
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. S. Grinberga
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. E. Lukevics
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abele, R., Abele, E., Rubina, K. et al. Synthesis and Cytotoxicity of 3-(Hetarylthio)-1-propynyl(trimethyl)silanes. Chemistry of Heterocyclic Compounds 38, 867–872 (2002). https://doi.org/10.1023/A:1020650224525

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1020650224525

Search

Navigation