Synthesis of 4-(N4-methyl-5-aryl-1,2,4-triazole-5-ilmethylthio) cresoxyacetic acids and their sulfonic analogues of new potential PPARδ/β agonists

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A nine-stage scheme for the synthesis of 4-( N 4-methyl-5-aryl-1,2,4-triazole-5-ilmethylthio) cresoxyacetic acids of new potential PPARδ/β agonists based on substituted benzoic acids has been developed. Their sulfon-containing analogues were obtained from the intermediate esters of such acids.

About the authors

D. V Minin

Mendeleev University of Chemical Technology

Email: minin30@mail.ru

S. V Popkov

Mendeleev University of Chemical Technology

Email: minin30@mail.ru

G. V Tsaplin

Mendeleev University of Chemical Technology

Email: minin30@mail.ru

References

  1. Evans R.M., Mangelsdorf D.J. Cell. 2014, 157, 255-266. doi: 10.1016/j.cell.2014.03.012
  2. Ciocoiu C.C., Nikoli N., Nguyen H.H., Thoresen G.H., Aasen A.J., Hansen T.V. Eur. J. Med. Chim. 2010, 45, 3047-3055. doi: 10.1016/j.ejmech.2010.03.035
  3. Pereira R., Claudine Gaudon C., Iglesias B., Germain P., Gronemeyer H., de Lera A.R. Bioorg. Med. Chem. Lett. 2006, 16, 49-54. doi: 10.1016/j.bmcl.2005.09.060
  4. Batista F.A.H., Trivella D.B.B., Bernardes A., Gratieri J., Oliveira P.S.L., Figueira A.C.M., Webb P., Polikarpov I. PLoS ONE. 2012, 7, 1-7. doi: 10.1371/journal.pone.0033643
  5. Holla B., Kalluraya B., Sridhar K., Drake E., Thomas L., Bhandary K., Levine M. Eur. J. Med. Chem. 1994, 29, 301-308. doi: 10.1016/0223-5234(94)90100-7
  6. Haber J. Cas. Lek. Cesk. 2001, 140, 596-604.
  7. Ergenc N., Ilhan E., Ötük G. Pharmazie. 1992, 47, 59-60.
  8. Rollas S., Kalyoncuoğlu N., Sür-Altiner D., Yegenoğlu Y. Pharmazie. 1993, 48, 308-309.
  9. Mir I., Siddiqui M., Comrie A. Tetrahedron. 1970, 26, 5235-5238. doi: 10.1016/s0040-4020(01)98732-0
  10. Holla B., Veerendra B., Shivananda M. Eur. J. Med. Chem. 2003, 38, 759-767. doi: 10.1016/S0223-5234(03)00128-4
  11. Yale H., Piala J. J. Med. Chem. 1966, 9, 42-46. doi: 10.1021/jm00319a010
  12. Mhasalkar M., Shah M., Nikam S., Anantanarayanan K., Deliwala C. J. Med. Chem. 1970, 13, 672-674.
  13. Shaker R. Arkivoc. 2006, 9, 59-112. doi: 10.3998/ark.5550190.0007.904
  14. Dittrich-Wengenroth E., Otteneder M., Bischoff H., Woltering M., Heckroth H. Пат. 2512502 (2004). Канада. С.A. 2005, 143, 153366.
  15. Connor S., Mantlo N., Zhu G., Herr R. Пат. 7544707 (2009). США. C.A. 2010, 41, 106371.
  16. Jaiswal R., Pamar S., Singh S., Bartwal J. J. Heterocycl. Chem. 1979, 16, 561-565. doi: 10.1002/jhet.5570160331
  17. Чурилов И.С. Диc. … канд. хим. наук. М., 2008.
  18. Sung K., Lee A. J. Heterocycl. Chem. 1992, 29, 1101-1109. doi: 10.1002/jhet.5570290512
  19. Ivanova N.V., Sviridov S.I., Shorshnev S.V., Stepanov A.E. Synthesis. 2006, 2006, 156-160. doi: 10.1055/s-2005-921754
  20. Thevis M., Moller I., Thomas A., Beuck S., Rodchenkov G., Bornatsch W., Geyer H., Schanzer W. Anal. Bioanal. Chem. 2010, 396, 2479-2491. doi: 10.1007/s00216-009-3283-x
  21. Thevis M., Moller I., Thomas A., Beuck S., Rodchenkov G., Bornatsch W., Geyer H., Schanzer W. Anal. Bioanal. Chem. 2010, 396, 2479-2491. doi: 10.1007/s00216-009-3283-x
  22. Минин Д.В., Попков С.В., Бурдейный М.Л., Гончаров В.М., Василевский С.В. Fine Chem. Technol. 2019, 14, 60-69. doi: 10.32362/2410-6593-2019-14-3-60-69
  23. Banerjee A., Banerjee G.C., Dutt S., Banerjee S., Samaddar H. J. Indian Chem. Soc. 1980, 57, 640.
  24. Houlihan W.J., Gogerty J.H., Parrino V.A., Ryan E. J. Med. Chem. 1983, 26, 765.
  25. Al-Aseer M.A., Allisson B.D., Smith S.G. J. Org. Chem. 1985, 50, 2715.
  26. Yagupol'skii L.M. Ukr. Khim. Zh. 1957, 23, 634.
  27. Horwitz J.P. J. Org. Chem. 1954, 19, 194.

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences