5-Ethoxymethylidene-4-thioxo-2-thiazolidinone as versatile building block for novel biorelevant small molecules with thiopyrano[2,3-D][1,3]thiazole Core

Synthetic Communications

Volumn 44, Issue 2, 2014, Pages 237-244

  Atamanyuk, Dmytro ^a   Zimenkovsky, Borys ^a   Atamanyuk, Vasyl ^a   Lesyk, Roman ^a  

^a DANYLO HALYTSKY LVIV NATIONAL MEDICAL UNIVERSITY   (Ukraine)

Author keywords

5 ethoxymethylidene 4 thioxo 2 thiazolidinone; Biological activity; hetero Diels Alder reaction; thiopyrano 2,3 D thiazole

Indexed keywords

2 OXO 2H THIOPYRANO[2,3 D][1,3]THIAZOLE 6 CARBOXYLIC ACID; 5 ETHOXYMETHYLIDENE 4 THIOXO 2 THIAZOLIDINONE; 5,10 DIHYDRO 2H BENZO[6,7]THIOCHROMENO[2,3 D][1,3]THIAZOLE 2,5,10 TRIONE; THIAZOLIDINE DERIVATIVE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; DIELS ALDER REACTION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFLUENZA VIRUS A H1N1; INFLUENZA VIRUS A H3N2; INFLUENZA VIRUS A H5N1; INFLUENZA VIRUS B; MEASLES VIRUS; NONHUMAN; PARAINFLUENZA VIRUS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RESPIRATORY SYNCYTIAL PNEUMOVIRUS; SARS CORONAVIRUS;

EID: 84887445169     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.800552     Document Type: Article

References (29)

1. Lesyk, R. B.;, Zimenkovsky, B. S. Curr. Org. Chem. 2004, 8, 1547-1577.
2. Brown, F. C. Chem. Rev. 1961, 61, 463-521.
3. Singh, S. P.;, Parmar, S. S.;, Raman, K.;, Stenberg, V. I. Chem. Rev. 1981, 81, 175-203.
4. Theocharis, S.;, Margeli, A.;, Kouraklis, G. Curr. Med. Chem. Anti-canc. Agents 2003, 3, 239-251.
5. Theocharis, S.;, Margeli, A.;, Vielh, P.;, Kouraklis, G. Cancer Treatment Rev. 2004, 30, 545-554.
6. Sing, W. T.;, Lee, C. L.;, Yeo, S. L.;, Lim, S. P.;, Sim, M. M. Bioorg. Med. Chem. Lett. 2001, 11, 91-94.
7. Rao, A.;, Balzarini, J.;, Carbone, A.;, Chimirri, A.;, De Clercq, E.;, Monforte, A. M.;, Monforte, P.;, Pannecouque, C.;, Zappalà, M. Farmaco 2004, 59, 33-39.
8. Murphy, G. J.;, Holder, J. C. Trends Pharmacol. Sci. 2000, 21, 469-474.
9. Bailey, C. J. Trends Pharmacol. Sci. 2000, 21, 259-265.
10. Reginato, M. J.;, Lazar, M. A. Trends Endocrinol. Metab. 1999, 10, 9-13.
11. Tomasic, T.;, Masic, L. P. Expert Opin. Drug Discov. 2012, 7 (7), 549-560.
12. Baell, J. B. Future Med. Chem. 2010, 2 (10), 1529-1546.
13. Baell, J. B.;, Holloway, G. A. J. Med. Chem. 2010, 53, 2719-2740.
14. Mendgen, T.;, Steuer, C.;, Klein, C. D. J. Med. Chem. 2012, 55, 743-753.
15. Lesyk, R.;, Zimenkovsky, B.;, Atamanyuk, D.;, Jensen, F.;, Kiec-Kononowicz, K.;, Gzella, A. Bioorg. Med. Chem. 2006, 14, 5230-5240.
16. Matiychuk, V. S.;, Lesyk, R. B.;, Obushak, M. D.;, Gzella, A.;, Atamanyuk, D. V.;, Ostapiuk Yu, V.;, Kryshchyshyn, A. P., Tetrahedron Lett. 2008, 49, 4648-4651.
17. Atamanyuk, D.;, Zimenkovsky, B.;, Lesyk, R. J. Sulfur Chem. 2008, 29, 151-162.
18. Kryshchyshyn, A.;, Atamanyuk, D.;, Lesyk, R. Sci. Pharm. 2012, 80 (3), 509-529.
19. Atamanyuk, D.;, Zimenkovsky, B.;, Atamanyuk, V.;, Nektegayev, I.;, Lesyk, R. Sci. Pharm. 2013,. 81 (2), 423-436.
20. Zelisko, N.;, Atamanyuk, D.;, Vasylenko, O.;, Grellier, P.;, Lesyk, R. Bioorg. Med. Chem. Lett. 2012, 22, 7071-7074.
21. Kaminskyy, D.;, Vasylenko, O.;, Atamanyuk, D.;, Gzella, A.;, Lesyk, R. Synlett 2011, 10, 1385-1388.
22. Ead, H. A.;, Abdallah, S. O.;, Kassab, N. A.;, Metwalli, N. H.;, Saleh, Y. E. Arch. Pharm. (Weinheim) 1987, 320, 1227-1231.
23. Boyd, M. R.;, Paull, K. D. Drug Dev. Res. 1995, 34, 91-109.
24. Boyd, M. R.; In Cancer Drug Discovery and Development: Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials, and Approval;; B. A. Teicher. (Ed.); Humana Press: Totowa, NJ; 1997; pp. 23-42.
25. Monks, A.;, Scudiero, D.;, Skehan, P.;, Shoemaker, R.;, Paull, K.;, Vistica, D.;, Hose, C.;, Langley, J.;, Cronise, P.;, Vaigro-Wolff, A. J. Natl. Cancer Inst. 1991, 83, 757-766.
26. Monks, A.;, Scudiero, D. A.;, Johnson, G. S.;, Paull, K. D.;, Sausville, E. A. Anti-cancer Drug Dis. 1997, 12, 533-541.
27. Shoemaker, R. H.;, Scudiero, D. A.;, Melillo, G.;, Currens, M. J.;, Monks, A. P.;, Rabow, A. A.;, Covell, D. G.;, Sausville, E. A. Curr. Top. Med. Chem. 2002, 2, 229-246.
28. Plowman, J.;, Dykes, D. J.;, Hollingshead, M.;, Simpson-Herren, L.;, Alley, M. C. Human tumor xenograft models in NCI drug development. In Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials, and Approval; B. Teicher. (Ed.); Humana Press: New York, 1997; pp. 101-125.
29. Antimicrobial Acquisition and Coordinating Facility, sponsored by the NIAID of the US National Institutes of Health. Available at http://niaid-aacf. org