Methods of synthesis and properties of thiazolopyridines

T. I. Chaban

Abstract


 

The review systematizes the theoretical and experimental data concerning methods of synthesis of condensed thiazolopyridines, which at present have been insufficiently studied, the prospects for their application in the directed synthesis of new physiologically active substances. The recent developments in their pharmacology have been also analyzed. The available methods for the synthesis of condensed thiazolopyridines can be divided into two fundamentally different approaches. The first approach is based on annelation of the thiazolidine or thiazole cycle to the pyridine ring, and the second one use pyridine derivatives as starting materials; their functional groups make it possible to change the pyridine ring. Methods for obtaining thiazolopyridines using solid media carriers, and their synthesis with domino reactions deserve a particular attention. Generalization of the scientific data published confirms that the condensed thiazolopyridines exhibit various biological effects. In particular, they are characterized by analgesic, anti-inflammatory, antimicrobial, antioxidant and antifungal activities. Due to the inhibitory action on integrally linked kinase the specified class of compounds can eliminate the hyperproliferative disorders in the living organisms. It has been found that these derivatives exhibit the antidiabetic, antibacterial and anti-tuberculosis action. It is known that derivatives of thiazolopyridines have shown a positive effect in the treatment of sexual dysfunction. Thiazolopyridine derivatives containing the α-amino phosphonate residue at 2 position of the basic heterocycle exhibit a significant anticancer effect.



Keywords


thiazolopyridine; synthesis; properties; condensed; pharmacological activity

Full Text:

PDF

References


Brown F. C. Chemical Reviews, 1961, Vol. 61, No.5, pp.463-521.

Singh S. P., Parmar S. S., Raman K. et. al. Chemical Reviews, 1981, Vol. 81, No.2, pp.175-203.

Zimenkovsky B. S., Lesyk R. B. 4-Тhiazolidony. Chimiya, fiziologichna diya, perspektyvy (4-Thiazolidones. Chemistry, physiological action, perspectives). Vinnycya, Nova knyga, 2004, 106 p.

Lesyk R. B., Zimenkovsky B. S. Current Organic Chemistry, 2004, Vol. 8, No.16, pp.1547-1579.

Komaritsa I. D. Chemistry of Heterocyclic Compound, 1968, No.3, pp.436-437.

Komaritsa I. D. Chemistry of Heterocyclic Compound, 1989, No.11, pp.1547-1549.

Chaban T. I., Zimenkovskii B. S., Komaritsa I. D. et. al. Russ. J. Org. Chem., 2012, Vol. 48, Issue 2, pp.268-270.

Chaban T. I., Ogurtsov V. V., Chaban I. G. et al. Zhurnal organichnoi ta farmacevtichnoi khimii – Journal of organic and pharmaceutical chemistry, 2012, Vol. 10, No.2(38), pp.70-76.

Chaban T. I., Panchuk R. R., Klenina O. V. et al. Biopolymers and Cell, 2012, Vol. 28, No.5, pp.389-396.

Chaban T. I., Ogurtsov V. V., Chaban I. G. et al. Phosphorus, Sulfur, and Silicon and the Related Elements, 2013, Vol. 188, pp.1611-1620.

Dudinov A. A., Lichitsky B. V., Antonov I. А. et al. Russian Chemical Bulletin., 2008, No.8, pp.1707-1710.

Lichitsky B., Komogortsev A., Dudinov A. et al. The 5th Eurasian Meeting on Heterocyclic Chemistry, Book of abstracts, 2008, Kuwait, p.124.

Lichitsky B., Komogortsev A., Dudinov A. et al. The 23nd International Symposium on the Organic Chemistry of Sulfur, Abstracts, 2008, Moscow, pp.100-102.

Lichitsky B., Komogortsev A., Dudinov A. et al. The III Youth conference Institute of organic Chemistry Russian Academy of Sciences, 2009, Moscow, U4-15-17.

Комогорцев А. Н. Трехкомпонентная конденсация гетероциклических аминов с карбонильными соединениями и кислотой Мельдрума: автореф. дисс. на соискание ученой степени канд. хим. наук: спец. 02.00.03 «Органическая химия» / А. Н. Комогорцев. – Москва, 2009. – 26 с.

Hayakawa I., Tanaka Y. Heterocycles, 1984, Vol. 22, No.8, pp. 1697-1700.

Schäfer H., Hartmann H., Gewald К. J. Prakt. Chem., 1974, Vol. 316, No.1, pp.19-25.

Leysen D. C., Haemers A., Bollaert W. J. Het. Chem., 1984, Vol. 21, No.2, pp.401-406.

Shafiee A., Ghazar H. J. Het. Chem., 1986, Vol. 23, No.4, pp.1171-1173.

El-Sayed I. El-Desoky, Aboul- Fetouh S., Metwally M. A. J. Chem. Tech. & Biotechnol., 1996, Vol. 67, No.2, pp.153-156.

Flaig R., Hartmann H. Monatshefte für Chemie, 1997, Vol. 128, No.10, pp.1051-1060.

Yarovenko V. N., Nikitin A. S., Zavarzyn I. V. et al. Zhurnal organicheskoi khimii, 2007, Vol. 43, No.9, pp.1368-1374.

Никитина А. С. Синтез гетероциклических соединений на основе тиогидразидов оксаминовых кислот: автореф. дисс. на соискание ученой степени канд. хим. наук: – спец. 02.00.03 «Органическая химия» / А. С. Никитина. – Москва, 2009. – 18 с.

Renskyy M. A, Zyabrev V. S., Drach B. S. Zhurnal obshchey khimii, 2002, Vol. 72, No.11, pp.1931-1932.

Ренський М. О. Нові перетворення 1,2,4-тіадіазол-5(2н)-імінів та їх солей у похідні інших азотистих гетероциклів: автореф. дис. на здобуття вченого ступеня канд. хім. наук: спец. 02.00.03 «Органічна хімія» / М. О. Ренський. – К., 2005. – 19 с.

Krayushkin M. M., Yarovenko V. N., Sedishev I. P. et al. Mendeleev Commun., 2005, Vol. 15, No.4, pp.151-152.

Krayushkin M. M., Sedishev I. P., Yarovenko V. N. et al. Russ. J. Org. Chem., 2008, Vol. 44, No.3, pp.407-411.

Iaroshenko V. O., Volochnyuk D. M., Kryvokhyzha N. V. et al. Synthesis, 2008, Vol. 15, pp.2337-2346.

Artyomov V. A., Ivanov V. L., Shestopalov A. M. et al. Tetrahedron, 1997, Vol. 53, No.39, pp.13351-13360.

Иванов В. Л. Каскадные реакции в синтезе конденсированных пиридинов и пиримидинов: автореф. дисс. на соискание ученой степени канд. хим. наук: спец. 02.00.03 «Органическая химия» / В. Л. Иванов. – М., 1997. – 20 с.

Pat. DE 233010. – Publ. 03.01.1974. Chem. Abstr., 1974, Vol. 80, 95916 p.

Suzuki N., Dohmori R. Chem. Pharm. Bull., 1979, Vol. 27, No.2, pp. 410-418.

Couture A., Grandclaudon P., Huguerre E. J. Het. Chem., 1987, Vol. 24, No.6, pp.1765-1770.

Couture A., Huguerre E., Grandclaudon P. Synt. Comm., 1989, Vol. 19, No.3, pp.713-719.

Zhu L., Zhang M., Dai M. J. Het. Chem., 2005, Vol. 42, No.4, pp.727-730.

Kulkarni D. G., Lokhande S. R. Ind. J. Pharm., 1981, Vol. 43, pp.37-39.

Altland H. W., Molander G. A. J. Het. Chem., 1977, Vol. 14, No.1, pp.129-134.

Altland H. W. J. Org. Chem., 1976, Vol. 41, No.21, pp.3395-3398.

Pat. US 2005065151; Publ. 24.03.2005, http://www.espacenet.com.

Tsuruoka A., Kaku Y., Kakinuma H. et al. Chem. Pharm. Bull., 1998, Vol. 46, No.4, pp.623-630.

Smith K., Lindsay C. M., Morris J. K. Chem. Ind (London), 1988, pp.302-303.

Ma E. Molecules, 2003, Vol. 8, pp.678-686.

El-Hiti G. A. Monatshefte fuer Chemie, 2003, Vol. 134, No.6, pp.837-841.

Smith K., Anderson D., Matthews I. Sulfur Letters, 1995, Vol. 18, No.2, pp.79-95.

Fridman S. G. Zhurnal obshchey khimii, 1956, Vol. 26, pp.613-617.

Fridman S. G. Zhurnal obshchey khimii, 1956, Vol. 26, pp.864-867.

Walczyn´ski K., Zuiderveld O. P., Timmerman H. European Journal of Medicinal Chemistry, 2005, Vol. 40, No.1, pp.15-23.

Gu and C. Jin L. Org. Biomol. Chem., 2012, Vol. 10, pp.7098-7102.

Couture A., Grandclaudon P. Heterocycle, 1984, Vol. 22, No.6, pp.1383-1385.

Kramberger L., Lorencak Р., Polanc S. et al. J. Het. Chem., 1975, Vol. 12, No.2, pp.337-342.

Zavarzin I. V., Krayushkin M. M., Yarovenko V. N. et al. Russian Chemical Bulletin, 2004, No.6, pp.1299-1301.

Zavarzin I. V., Smirnova N. G., Yarovenko V. N. et al. Russ. Chem. Bull., 2004, Vol. 53, No.6, pp.1353-1354.

Смирнова Н. Г. Монотиооксамиды в синтезе конденсированных гетероциклических структур: автореф. дисс. на соискание ученой степени канд. хим. наук: спец. 02.00.03 «Органическая химия» / Н. Г. Смирнова. – М., 2006. – 20 с.

Заварзин И. В. Монотиооксамиды и тиогидразиды оксаминовых кислот в органическом синтезе: автореф. дисс. на соискание ученой степени докт. хим. наук: спец. 02.00.03 «Органическая химия» / И. В. Заварзин. – М., 2009. – 48 с.

Matysiak J., Karpin´ska M., Niewiadomy A. et al. Chemistry & Biodiversity, 2012, Vol. 9, No.1, pp.48-56.

Taeho Lee, Doohyun Lee, Ill Young Lee et al. J. Comb. Chem, 2010, Vol. 12, No.1, pp.95-99.

Shestopalov A. M., Rodinovskaya L. A., Shestopalov A. A. Tetrahedron, 2010, Vol. 66, No.46, pp.8945-8948.

Shestopalov A. M., Rodinovskaya L. A. Proceedings of the Fourth International Conference “Modern aspects of heterocyclic chemistry”, St. Petersburg, 2010, pp.361-363.

Komaritsa I. D., Chaban I. G., Gеrman V. М. Pharmacevticheskoiy zhurnal, 1992, No.4, pp.39-43.

Al-Thebeiti Marzoog S. Il Farmaco. 2000, Vol. 55, pp.109-118.

Ulrich H. Georg Thieme Verlag: Stuttgart – New York, 2002, Vol. 11, pp.835-912.

El-Hiti G. A. Monatshefte fuer Chemie. 2003, Vol. 134, pp.837-841.

А.с. 1262931 СССР; заявл. 06.12.84 / ДСП.

А.с. 1282512 СССР; заявл. 14.06.85 / ДСП.

Pat. WO2004011460 – Publ. 05.02.2004. Chem. Abstr., 2004, Vol. 140, 163862 p.

Pat. WO 2005037845. – Publ. 28.04.2005, No.WO 2004US34397. – http://www.espacenet.com.

Pat. WO 2004099204. – Publ.18.11.2004, N.WO2004SE00694. – http://www.espacenet.com.

Pat. WO 2004011460. – Publ. 05.02.2004. Chem. Abstr., 2004, Vol. 140, 63862 p.

Pat. WO 2009147431. – Publ. 10.12.2009, No.GB2009/050609. – http://www.espacenet.com.

Chaban T., Klenina O., Drapak I. et al. Сh&ChT, 2014, Vol. 8 (3), pp.287-292.

Chaban T. I., Ogurtsov V. V., Komaritsa I. D. et al. Klinichna farmaciya, farmakoterapiya ta medychna standartyzaciya – Clinical pharmacy, pharmacotherapy and medical standardization, 2011, No.1-2, pp.208-213.

Klenina O. V., Chaban T. I., Ogurtsov V. V. et al. Zhurnal organichnoi ta farmacevtichnoi khimii – Journal of organic and pharmaceutical chemistry, 2014, Vol. 12, No.1(45), pp.60-68.

Pat. WO 2003101994. – Publ. 11.12.2003. Chem. Abstr., 2004, Vol. 140, 27845 p.

Kulkarni S. S., Newman A. H. Bioorg. Med. Chem. Lett., 2007, Vol. 17, pp.2987-2991.

Lin R., Johnson S. G., Connolly P. J. et al. Bioorg. Med. Chem. Lett., 2009, Vol. 19, pp.2333-2337.

Komoriya S., Kobayashi S., Osanai K. et al. Bioorg. Med. Chem., 2006, Vol. 14, pp.1309-1330.

Singh B., Bacon E. R., Lesher G. Y. et al. J. Med. Chem., 1995, Vol. 38, pp.2546-2550.


GOST Style Citations






DOI: https://doi.org/10.24959/ophcj.15.811

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)