The synthesis and the biological activity of azolylthioacetic acids

Authors

  • V. O. Chornous Bukovinian State Medical University, Ukraine
  • A. O. Palamar Bukovinian State Medical University, Ukraine
  • A. M. Grozav Bukovinian State Medical University, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.895

Keywords:

azolylthioacetic acids, carboxymethyl thiol fragment, synthesis, biological activity

Abstract

The review systematizes the published data concerning the methods of synthesis of azoles (imidazoles, oxazoles, thiazoles, pyrazoles, triazoles, and tetrazoles) functionalized by the carboxymethyl thiol fragment; the results of studies of the biological activity of this class of compounds have been also analysed. Today the main directions for the synthesis of azolylthioacetic acids and their derivatives are reactions of azoles that contain the thiol group with haloacetic acids and their derivatives, and the nucleophilic substitution of halogen in the haloazoles under the action of thioglycolic acid. Moreover, the addition of thioles to multiple bonds, activated with electron withdrawing groups has found its application together with formation of the azole cycle from heterofunctional systems that already contain the component of thioacetic acid. To obtain polyfunctional derivatives of azolylthioacetic acids the modification of azole functional groups that already contain the fragment of thioacetic acid is sometimes used. The summary of the published data gives strong reasons to assert that the derivatives of azolylthioacetic acids are characterized by diverse biological effects. For instance, they are characterized by the antioxidant, hypoglycemic, antitubercular, analgesic, antiviral, antimicrobial, and antifungal activity. The material analysed indicates that the search for new bioactive compounds among the azolylthioacetic acids is very promising.

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References

  1. Mashkovskii M. D. Drugs. Moscow, “Novaya Volna”: Publisher Umerenkov, 2012, pp.917-924.
  2. Farmacevty`chna khimiya: Pidruchny`k / Za zag. red. P. O. Bezuglogo. Vinny`cya: Nova Kny`ga, 2008, pp.309-354.
  3. My`tny`k Z. N., Kolesny`k Yu. M. Zaporozhsky`j medy`cy`nsky`j zhurnal, 2010, T. 12, No.5, pp.7-9.
  4. Tiotriazolin. Farmakologicheskie aspektyi i klinicheskoe primenenie: Monografiya / I. A. Mazur, N. A. Voloshin, I. S. Chekman, Zaporozhe-Lvov, 2005, 146 p.
  5. Katritskiy A. Himiya geterotsiklicheskih soedineniy / A. Katritskiy, Dzh. Lagovskaya. Moskva: IL, 1963, 288 p.
  6. Iddon B., Khan N., Lim B. L. J. Chem. Soc., Perkin Trans. 1, 1987, pp.1437-1443.
  7. Chornous V. A., Palamar A. A., Yaremiy I. N., Vovk M. V. Himiko-farmatsevticheskiy zhurnal, 2013, T. 47, No.2, pp.28-30.
  8. Mukherjee А., Kumar S., Seth M., Bhaduri A.P. Ind. J. of Chemistry. Section B Organic Chemistry Including Medicinal Chemistry, 1989, Vol. 28, No.5, pp.391-396.
  9. Crawford D. J. K., Maddocks J. L., Jones D. N., Szawlowski P. J. of Med. Chem., 1996, Vol. 39, No.14, pp.2690-2695.
  10. Al-Soud Y. A., Al-Masoudi N. A., De Clercq E., Paneccoque C. Heteroatom Chemistry, 2007, Vol. 18, No.4, pp.333-340.
  11. Toto P., Chenault J., Hakmaoui A. E., Akssira M., Guillaumet G. Synthetic Communications, 2008, Vol. 38, No.5, pp.674-683.
  12. Galal S. A., Khairat S. H. M., Ragab F. A. F, Abdelsamie A. S., Ali M. M., Soliman S. M., Mortier J., Wolber G. Eur. J. of Med. Chem., 2014, No.86, pp.122-132.
  13. Пат. US2012071489 (2012). Заявл.: 16.04.2010. Опубл: 22.03.2012. [Електронний ресурс] https://data.epo.org
  14. Пат. EP1775298 (2007). Заявл.: 01.07.2005. Опубл.: 18.04.2007. [Електронний ресурс] https://data.epo.org
  15. Ilyn A. P., Loseva M. V., Vvedensky V. Y., Putsykina E. B., Tkachenko S. E., Kravchenko D. V., Khvat A. V., Krasavin M. Y., Ivachtchenko A. V. J. Org. Chem., 2006, Vol. 71, No.7, pp.2811-2819.
  16. Dalinger I. L., Vatsadze I. A., Shkineva T. K., Popova G. P., Schvelev S. A. Mendeleev Communications, 2010, Vol. 20, No.5, pp.253-254.
  17. Dalinger I. L., Vatsadze I. A., Shkineva T. K., Popova G. P., Shevelev S. A., Nelyubina Y. V. J. of Heterocyclic Chem., 2013, Vol. 50, No.4, pp.911-924.
  18. Buchanan J. G., Jumaah A. O., Kerr G., Talekar R. R., Wiqhtman R. H. J. of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 1991, No.5, pp.1077-1083.
  19. Burger K., Geith K., Hubl D. Synthesis, 1988, No.3, pp.199-203.
  20. Adb-Alla M. A., Ahmed A. N., El-Zohry M. F., Omar F. A. Collection of Czechoslovak Chemical Communications, 1992, Vol. 57, No.7, pp.1547-1552.
  21. Пат. US4935438 (1990). Заявл.: 29.12.1987. Опубл.: 19.01.1990. [Електронний ресурс] https://data.epo.org
  22. Pesson M. Bulletin de la Societe Chimique de France, 1961, pp.1581-1585.
  23. Пат. US20110268801. Заявл.: 30.06.2011. Опубл.: 03.11.2011. [Електронний ресурс] https://data.epo.org
  24. Wang J., Tang W., Fang G., Pan M., Wang S. J. of the Chinese Chemical Society, 2011, Vol. 58, No.4, pp.463-469.
  25. Пат. US6342608 B1 (2002). Заявл.: 30.01.2001. Опубл.: 29.01.2002. [Електронний ресурс] https://data.epo.org
  26. Pellei M., Alidori S., Benetollo F., Lobbia G. G., Mancini M., Santini C. J. of Organometallic Chem., 2008, Vol. 693, No.6, pp.996-1004.
  27. Lumb K. J., DeCarr L. B., Milardo L. F. J. Med. Chem., Vol. 50, No.9, pp.2264-2268.
  28. Пат. WO2006/121860 A2 (2006). Заявл.: 05.05.2006. Опубл.: 16.11.2006. [Електронний ресурс] http://patentscope.wipo.int
  29. Пат. WO2006/121904 (2006). Заявл.: 27.10.2006. Опубл.: 16.11.2006. [Електронний ресурс] http://patentscope.wipo.int
  30. Пат. WO2011/37780 (A1) (2011). Заявл.: 14.09.2010. Опубл.: 31.03.2011. [Електронний ресурс] http://patentscope.wipo.int
  31. Пат. WO 2010/135530 A2 (2010). Заявл.: 20.05.2010. Опубл.: 25.11.2010. [Електронний ресурс] http://patentscope.wipo.int
  32. Gagnon A., Landry S., Coulombe R., Jakalian A., Guse I., Thavonekham B., Bonneau P. R., Yoakim C., Simoneau B. Bioorg. Med. Chem. Lett., 2009, No.19(4), pp.1199-1205.
  33. Пат. WO 2005/118575 A1 (2005). Заявл.: 30.05.2005. Опубл.: 15.12.2005. [Електронний ресурс] http://patentscope.wipo.int
  34. Ahluwalia V. K., Sharma H. R., Tyagi R. Tetrahedron, 1987, Vol. 43, No.6, pp.1141-1146.
  35. Пат. EP1939181 A1 (2008). Заявл.: 27.12.2006. Опубл.: 02.07.2008. [Електронний ресурс] https://data.epo.org
  36. Maliszewska-Guz A., Wujec M., Pitucha M., Dobosz M., Chodkowska A., Mazur L., Koziol A. E. Collection of Czechoslovak Chemical Communications, 2005, No.70, pp.51-62.
  37. Altintop M. D., Kaplancikli Z. A., Ciftci G. A., Demirel R. Eur. J. of Med. Chem., 2014, No.74, pp.264-277.
  38. Sayed G. H., Radwan A., Hamed A. A., Boraie W. E. Bulletin of the Chem. Soc. of Japan, 1993, Vol. 66, No.2, pp.477-482.
  39. Пат. WO 2014008295 A1 (2014). Заявл.: 02.07.2013. Опубл.: 09.01.2014. [Електронний ресурс] http://patentscope.wipo.int
  40. Popiolek L., Dobosz M., Chodkowska A., Kosikowska U., Malm A., Mazur L., J. of Heterocyclic Chem., 2011, No.48, pp.339-346.
  41. Buchanan J., McCaig A., Wightman R. J. of the Chem. Soc., Perkin Transactions 1, 1990, No.4, pp.955-963.
  42. Attanasi O. A., Foresti F., Liao Z., Serra-Zanetti F. J. of Org. Chem., 1995, No.60, pp.149-155.
  43. Bakulev V. A., Berseneva V. S., Belskaia N. P., Morzherin Y. Y., Zaitsev A., Dehaen W., Luyten I., Toppet S. Organic and Biomolecular Chem., 2003, No.1, pp.134-139.
  44. Asgharian-Sheykhi F., Hassanabadi A., Akhgar M. R., Karbalaei-Harofteh M., Khajehpour E. J. of Chem. Res., 2013, Vol. 37, No.9, pp.523-525.
  45. Yavari I., Alizadeh A., Anary-Abbasinejad M. Phosphorus, Sulfur and Silicon and the Related Elements, 2003, Vol. 178, No.2, pp.269-277.
  46. Gallagher J. F., Coleman C. M., O’Shea D. F. Acta Crystallographica Section C: Crystal Structure Communications, 2002, Vol. 58, No.3, pp.139-141.
  47. Bolgunas S., Clark D. А., Hanna W. S., Mauvais P. A., Pember S. O. J. of Med. Chem., 2006, Vol.49, No.15, pp.4762-4766.
  48. Chornous V. O., Palamar A. O., Yaremij I. M., Burdenyuk I. P., Vovk M. V. Visny`k farmaciyi, 2013, No.2(74), pp.30-33.
  49. Пат. 92647, Україна (2014). Заявл.: 01.04.2014. Опубл.: 26.08.2014. Бюл. №16.
  50. Grozav A. M., Chornous V. O., Demydovska S. A., Palamar A. O., Vovk M. V. Farmacevty`chny`j zhurnal, 2012, No.6, pp.61-66.
  51. Chornous V. O., Palamar A. O., Grozav A. M., Yaremij I. M., Vovk M. V. Zhurnal organichnoyi ta farmacevty`chnoyi ximiyi, 2013, T. 11, No.4(44), pp.55-60.
  52. Maddila S., Palakondu L., Chunduri V. Der Pharmacia Lettre, 2010, Vol. 4, No.2, pp.393-402.
  53. Steenackers H. P. L., Ermolat’ev D. S., Savaliya B. Bioorg. & Med. Chem., 2011, Vol.19, No.11, pp.3462-3473.
  54. Chornous V. O., Palamar A. O., Grozav A. M., Yaremij I. M., Vovk M. V. Ukrayins`ky`j biofarmacevty`chny`j zhurnal, 2015, No.2, pp.79-84.
  55. Chornous V. O., Palamar A. O., Yaremij I. M., Yakovy`chuk N. D., Vovk M. V. Zaporiz`ky`j medy`chny`j zhurnal, 2014, No.2(83), pp.103-106.
  56. Belenichev I. F., Tishkin V. S., Dunaev V. V. Sb. nauch. trudov Zaporozhsk. med. instituta,1991, pp.323-325.
  57. Avramenko M. O., Nesterova N. O., Byelenichev I. F. Zb. nauk. statej. Zaporizhzhya, 1997, No.1, pp.3-13.
  58. Avramenko N. A., Chekrovskaya L. G., Katkevich R. I. Sb. nauch. trudov Zaporozhsk. med. instituta, 1991, pp.255-256.
  59. Yarosh O. K., Nagorna O. O., Kucherenko L. I., Bidnenko O. S. Farmakologiya ta likars`ka toksy`kologiya, 2014, No.2, pp.64-69.
  60. Byelenichev I. F., Pavlov S. V., Kucherenko L. I. Farmakologiya ta likars`ka toksy`kologiya, 2014, No.3, pp.3-11.
  61. Belenichev I., Pavlov S., Sokolik E., Mazur I., Buhtiyarova N., Kucherenko L. Molecular Pharmacol., 2011, Issue 3, No.1, pp.90-95.
  62. Пат. US2014309207 A1 (2010). Заявл.: 27.12.2006. Опубл: 02.07.2008. [Електронний ресурс] https://data.epo.org
  63. Пат. US2014309207 A1. Заявл.: 18.12.2012. Опубл: 16.10.2014. [Електронний ресурс] https://data.epo.org
  64. Пат. WO2005066145 A1 (2005). Заявл.: 06.01.2005. Опубл.: 21.07.2005. [Електронний ресурс] http://patentscope.wipo.int
  65. Пат. 49481, Україна (2010). Заявл.: 07.12.2009. Опубл.: 26.04.2010. Бюл. №8.
  66. Rajesha G., Mahadevan K. M., Satyanarayan N. D., Bhojya Naik S. Phosphorus, Sulfur and Silicon and the Related Elements, 2011, Vol. 186, No.8, pp.1733-1743.
  67. Parchenko V. V. Farmacevty`chny`j zhurnal, 2011, No.3, pp.49-53.
  68. Пат. 18863, Україна (2006). Заявл.: 13.06.2006. Опубл.: 15.11.2006. Бюл. №11.
  69. Пат. WO 2012108794 А3 (2012). Заявл.: 10.12.2011. Опубл.: 26.10.2012. [Електронний ресурс] http://patentscope.wipo.int
  70. Пат. 61715, Україна (2011). Заявл.: 17.01.2011. Опубл.: 25.07.2011. Бюл. №14.
  71. Пат. EP 2560642 A2 (2013). Заявл.: 29.03.2011. Опубл.: 27.02.2013. [Електронний ресурс] https://data.epo.org

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Published

2016-09-19

How to Cite

(1)
Chornous, V. O.; Palamar, A. O.; Grozav, A. M.; Vovk, M. V. The Synthesis and the Biological Activity of Azolylthioacetic Acids. J. Org. Pharm. Chem. 2016, 14, 4-23.

Issue

Vol. 14 No. 3(55) (2016)

Section

Original Researches

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