Synthesis and evaluation of anticancer activity of 5-ylidene-4-aminothiazol-2(5H)-one derivatives

Medicinal Chemistry

Volumn 11, Issue 6, 2015, Pages 517-530

  Kaminskyy, Danylo ^a   Subtel'na, Ivanna ^a   Zimenkovsky, Borys ^a   Karpenko, Olexandr ^b   Gzella, Andrzej ^c,d   Lesyk, Roman ^a  

^a DANYLO HALYTSKY LVIV NATIONAL MEDICAL UNIVERSITY   (Ukraine)

^b ENAMINE LTD   (Ukraine)

^c POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^d NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

4 (Imino)amino 2 thiazolidinone; Anticancer activity; Synthesis; X ray study

Indexed keywords

2 AMINOTHIAZOLE DERIVATIVE; 2,4 THIAZOLIDINEDIONE DERIVATIVE; 5 (3 PHENYLALLYLIDENE) 4 (4 ETHOXYPHENYLAMINO)THIAZOL 2(5H)ONE; 5 (3,4 DIMETHOXYPHENYLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (3HYDROXY 3 METHOXYPHENYLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (4 CHLOROPHENYLMETHYLIDENE) 4 (4 HYDROXYPHENYLAMINO)THIAZOL 2(5H)ONE; 5 (4 CHLOROYPHENYLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (4 DIETHYLAMINOPHENYLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (4 FLUOROPHENYLMETHYLIDENE) 4 (4 HYDROXYPHENYLAMINO)THIAZOL 2(5H)ONE; 5 (4 FLUOROPHENYLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (4 HYDROXYPHENYLMETHYLIDENE) 4 (4 HYDROXYPHENYLAMINO)THIAZOL 2(5H)ONE; 5 (4 HYDROXYPHENYLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (4 HYDROXYPHENYLMETHYLIDENE) 4 PHENYLAMINOTHIAZOL 2(5H)ONE; 5 (FURAN 2 YLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (FURAN 2 YLMETHYLIDENE) 4 PHENYLAMINOTHIAZOL 2(5H)ONE; 5 (THIOPHEN 2 YLMETHYLIDENE) 4 (4 HYDROXYPHENYLAMINO)THIAZOL 2(5H)ONE; 5 (THIOPHEN 2 YLMETHYLIDENE) 4 AMINOTHIAZOL 2(5H)ONE; 5 (THIOPHEN 2 YLMETHYLIDENE) 4 PHENYLAMINOTHIAZOL 2(5H)ONE; 5 YLIDENE 4 AMINOTHIAZOL 2(5H)ONE DERIVATIVE; 5 [4 (3,5 DIPHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL)PHENYLMETHYLIDENE] 4 AMINOTHIAZOL 2(5H)ONE; ANTINEOPLASTIC AGENT; CYCLODISONE; MITOGUAZONE; N,N DIBENZYLDAUNOMYCIN; PENTAMETHYLMELAMINE; PIPERAZINE; RHIZOXIN; TAMOXIFEN; TETRANDRINE; TRIAZINATE; UNCLASSIFIED DRUG; 5-YLIDENE-4- AMINOTHIAZOL-2(5H)-ONE; THIAZOLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL LINE; CONTROLLED STUDY; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; HYDROGEN BOND; MALE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TAUTOMER; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 84938819719     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/1573406411666150211112049     Document Type: Article

References (58)

1. Lesyk, R. B.; Zimenkovsky, B. S. 4-Thiazolidones: centenarian history, current status and perspectives for modern organic and medicinal chemistry. Curr. Org. Chem., 2004, 8, 1547-1577.
2. Jain, A. K.; Vaidya, A.; Ravichandran, V.; Kashaw, S. K.; Agrawal, R. K. Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorg. Med. Chem., 2012, 20, 3378-3395.
3. Lesyk, R. B.; Zimenkovsky, B. S.; Kaminskyy, D. V.; Kryshchyshyn, A. P.; Havryluk, D. Ya.; Atamanyuk, D. V.; Subtel'na, I. Yu.; Khyluk, D. V. Thiazolidinone motif in anticancer drug discovery. Experience of DH LNMU medicinal chemistry scientific group. Biopolym. Cell, 2011, 27, 107-117.
4. Tripathi, A. C.; Gupta, S. J.; Fatima, G. N.; Sonar, P. K.; Verma, A.; Saraf, S. K.; 4-Thiazolidinones: The advances continue... Eur. J. Med. Chem., 2013, 27, 52-77.
5. Prabhakar, Y. S.; Solomon, V. R.; Gupta, M. K.; Katti, S. B. QSAR studies on thiazolidines: a biologically privileged scaffold. Top. Heterocycl. Chem., 2006, 4, 161-249.
6. Tomasic, T.; Masic, L. P. Rhodanine as a privileged scaffold in drug discovery. Curr. Med. Chem., 2009, 16, 1596-1629.
7. Zhang, Y.; Wang, S.; Wu, S.; Zhu, S.; Dong, G.; Miao, Z.; Yao, J.; Zhang, W.; Sheng, C.; Wang, W. Facile construction of structurally diverse thiazolidinedione-derived compounds via divergent stereoselective cascade organocatalysis and their biological exploratory studies. ACS Comb. Sci., 2013, 15, 298-308.
8. Jain, V. S.; Vora, D. K.; Ramaa, C. S. Thiazolidine-2, 4-diones: progress towards multifarious applications. Bioorg. Med. Chem., 2013, 27, 1599-1620.
9. Kaminskyy, D.; Vasylenko, O.; Atamanyuk, D.; Gzella, A.; Lesyk, R. Isorhodanine and thiorhodanine motifs in the synthesis of fused thiopyrano[2, 3-d][1, 3]thiazoles. Synlett, 2011, 10, 1385-1388.
10. Matiychuk, V. S.; Lesyk, R. B.; Obushak, M. D.; Gzella, A.; Atamanyuk, D. V.; Ostapiuk, Y. V.; Kryshchyshyn, A. P. A new domino-Knoevenagel-hetero-Diels-Alder reaction. Tetrahedron Lett., 2008, 49, 4648-4651.
11. Lesyk, R.; Zimenkovsky, B.; Atamanyuk, D.; Jensen, F.; Kiec-Kononowicz, K.; Gzella A. Anticancer thiopyrano[2, 3-d][1, 3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies. Bioorg. Med. Chem., 2006, 14, 5230-5240.
12. Komaritsa, I. D. Studies on azolidones and their derivatives. Chem. Heterocycl. Compd., 1968, 4, 324-325.
13. Plevachuk, N. E.; Komaritsa, I. D. A study of azolidones and their derivatives, Chem. Heterocycl. Compd., 1970, 6, 144-145.
14. Pinson, J. A.; Schmidt-Kittler, O.; Frazzetto, M.; Zheng, Z.; Jennings, I. G.; Kinzler, K. W.; Vogelstein, B.; Chalmers, D. K.; Thompson, P. E. Synthesis and pharmacological evaluation of 4-iminothiazolidinones for inhibition of PI3 kinase. Aust. J. Chem., 2012, 65, 1396-1404.
15. Komogortsev, A. N;. Lichitsky, B. V.; Dudinov, A. A.; Krylov, K. S.; Bogacheva, A. M.; Kobeleva, O. I.; Barachevskii, V. A.; Krayushkin, M. M. Three-component condensation of iminoazolidines with aldehydes and 5-aminopyrazole. Mendeleev Commun., 2013, 23, 222-223.
16. Gewald, K.; Hain, U.; Schindler, R.; Gruner, M. Zur Chemie der 4-amino-thiazolin-2-thione, 2. Mitt. Monatsh. Chem., 1994, 125, 1129-1143.
17. Komaritsa I. D. Reaction of 4-iminothiazolidinone-2 with acetoacetic ester. Chem. Heterocycl. Compd., 1989, 25, 1297-1299.
18. Sayed, H. H.; Morsy, E. M. H.; Kotb, E. R. A facile novel synthesis and reactions of thiazolidin-4-one derivatives for antimicrobial agents. Synthetic Commun., 2010, 40, 2712-2722.
19. Chaban, T. I.; Ogurtsov, V. V.; Chaban, I. G.; Klenina, O. V.; Komarytsia, J. D. Synthesis and antioxidant activity evaluation of novel 5, 7-dimethyl-3H-thiazolo[4, 5-b]pyridines. Phosphorus Sulfur., 2013, 188, 1611-1620.
20. Subtel'na, I.; Atamanyuk, D.; Szymanska, E.; Kieć-Kononowicz, K.; Zimenkovsky, B.; Vasylenko, O.; Gzella, A.; Lesyk, R. Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity. Bioorg. Med. Chem., 2010, 14, 5090-5102.
21. Havrylyuk, D.; Zimenkovsky, B.; Lesyk, R. Synthesis and anticancer activity of novel nonfused bicyclic thiazolidinone derivatives. Phosphorus Sulfur., 2009, 184, 638-650.
22. Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Zaprutko, L.; Gzella, A.; Lesyk, R. Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity. Eur. J. Med. Chem., 2009, 44, 1396-1404.
23. Attardo, G.; Tripathy, S.; Gagnon, M. Arylmethylidene heterocycles as novel analgesics. WO Patent 2009/097695, August 13, 2009.
24. Kaminskyy, D.; Zimenkovsky, B.; Lesyk, R. Synthesis and in vitro anticancer activity of 2, 4-azolidinedione-acetic acids derivatives. Eur. J. Med. Chem., 2009, 44, 1396-1404.
25. Kaminskyy, D.; Bednarczyk-Cwynar, B.; Vasylenko, O.; Kazakova, O.; Zimenkovsky, B.; Zaprutko, L.; Lesyk, R. Synthesis of new potential anticancer agents based on 4-thiazolidinone and oleanane scaffolds. Med. Chem. Res., 2012, 21 3568-3580.
26. Kaminskyy, D. V.; Lesyk, R. B.; Structure-anticancer activity relationships among 4-azolidinone-3-carboxylic acids derivatives. Biopolym. Cell., 2010, 26, 136-145.
27. Kaminskyy, D.; Khyluk, D.; Vasylenko, O.; Zaprutko, L.; Lesyk, R. A facile synthesis and anticancer activity evaluation of spiro [thiazolidinone-isatin] conjugates. Sci. Pharm., 2011, 79, 763-777.
28. Kaminskyy, D.; Khyluk, D.; Vasylenko, O.; Lesyk, R. An efficient method for the transformation of 5-ylidenerhodanines into 2, 3, 5-trisubstituted-4-thiazolidinones. Tetrahedron Lett., 2012, 53, 557-559.
29. Kaminskyy, D. V.; Roman, O. M.; Atamanyuk, D. V.; Lesyk, R. B. 5-Ylidene-2-thioxo-4-thiazolidone-3-succinic acids and their derivatives: anticancer activity, QSAR-analysis. J. Org. Pharm. Chem., 2006, 4, 41-48 (in Ukrainian). CAN 148:33653.
30. Kim, H.-J.; Choo, H.; Cho, Y. S.; No, K. T.; Pae, A. N. Novel GSK-3β inhibitors from sequential virtual screening, Bioorg. Med. Chem., 2008, 16, 636-643.
31. Calderón, F.; Barros, D.; Bueno, J. M.; Coterón, J. M.; Fernández, E.; Gamo, F. J.; Lavandera, J. L.; León, M. L.; Macdonald, S. J. F.; Mallo, A.; Manzano, P.; Porras, E.; Fiandor, J. M.; Castro, J. An invitation to open innovation in malaria drug discovery: 47 quality starting points from the TCAMS, ACS Med. Chem. Lett., 2011, 2, 741-746.
32. Matsumoto, S.; Ono, K.; Tominari, Y.; Katoh, T.; Miwa, K.; Hasuoka, A.; Imamura, S. Nitrogen-containing heterocyclic compound. US Patent 20130072467, March 21, 2013.
33. Hasuoka, A.; Ono, K. Prophylactic or therapeutic agent for cancer. EP Patent 2450352, May 09, 2012.
34. Abdelaal, S. M.; Bauer, L. Synthesis of 2-amino-4-imino-4, 5-dihydrothiazoles from N-sulfonyl-α-chloroamidines and thiourea. J. Heterocycl. Chem., 1988, 25, 1849-1856.
35. Komaritsa, I. D.; Grishchuk, A. P. Azolidine-4-thiones, their derivatives and analogs. Chem. Heterocycl. Compd., 1968, 4, 517-519.
36. Labouta, I. M.; Salama, H. M.; Eshba, N. H.; Kader, O.; El-Chrbini, E. Potential anti-microbial: syntheses and in vitro antimicrobial evaluation of some 5-arylazo-thiazolidones and related compounds. Eur. J. Med. Chem., 1987, 22, 485-489.
37. Hahnemann, C.; Hartmann, H. On the reaction of thiazole-2, 4-diamines with isothiocyanates. Preparation and transformation of 2, 4-diaminothiazole-5-carbothioamides. Helv. Chim. Acta, 2003, 86, 1949-1965.
38. Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Cryst. Sect. B, 2002, 58, 380-388.
39. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. Typical interatomic distances: organic compounds. J. Chem. Soc. Perkin Trans. 2, 1987, 84, 1-19.
40. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Nat. Cancer Inst., 1991, 83, 757-766.
41. Boyd, M. R.; Paull, K. D. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev. Res., 1995, 34, 91-109.
42. Boyd, M. R. In: Cancer Drug Discovery and Development; Teicher, B. A. Ed.; Humana Press, 1997, Chap 2, pp. 23-43.
43. Shoemaker, R. H. The NCI60 human tumour cell line anticancer drug screen. Nat. Rev. Cancer, 2006, 6, 813-823.
44. Zaharevitz, D. W.; Holbeck, S. L.; Bowerman, C.; Svetlik, P. A. COMPARE: a web accessible tool for investigating mechanisms of cell growth inhibition. J. Mol. Graph. Modell., 2002, 20, 297-303.
45. Keskin, O.; Bahar, I.; Jernigan, R. L.; Beutler, J. A.; Shoemaker, R. H.; Sausville, E. A.; Covell, D. G. Characterization of anticancer agents by their growth inhibitory activity and relationships to mechanism of action and structure. Anticancer Drug Des., 2000, 15, 79-98.
46. Liu, C.; Gong, K.; Mao, X.; Li, W. Tetrandrine induces apoptosis by activating reactive oxygen species and repressing activity in human hepatocellular carcinoma. Int. J. Cancer. 2011, 129, 1519-1531.
47. Weistein, J. H.; Kohn, K. W.; Grever, M. R.; Viswanadhan, V. N.; Rubinstein, L. V.; Monks, A. P.; Scudiero, D. A.; Welch, L.; Koutsoukos, A. D.; Chiausa, A. J.; Paull, K. D. Neural computing in cancer drug development: predicting mechanism of action. Science, 1992, 258(5081), 447-451.
48. Muindi, J. R.; Newell, D. R.; Smith, I. E.; Harrap, K. R. Pentamethylmelamine (PMM): Phase I clinical and pharmacokinetic studies. Br. J. Cancer. 1983, 47, 27-33.
49. Arseneau, J. C.; Bundy, B.; Dolan, T.; Homesley, H.; Di Saia, P. J. Phase II study of Baker's antifol (triazinate, TZT, NSC-139, 105) in advanced squamous cell carcinoma of cervix. Am. J. Clin. Oncol., 1982, 5, 61-64.
50. Westendorf, J.; Marquardt, H.; Marquardt, H. Structure-activity relationship of anthracycline-induced genotoxicity in vitro. Cancer Res., 1984, 44, 5599-5604.
51. Gibson, N. W. Comparison of the in vitro cytotoxicity of cyclodisone with a series of structurally related analogues. Anticancer Drug. Des., 1988, 3, 199-204.
52. Raymond, P.; Warrell, Jr.; Burchenal, J. H. Methylglyoxalbis (guanylhydrazone) (Methyl-GAG): current status and future prospects. J. Clin. Oncol., 1983, 1, 52-65.
53. Grischuk, A. P.; Komaritsa, I. D.; Baranov, S. N. 4-Thionazolidones, derivatives and analogs. Chem. Heterocycl. Compd., 1966, 5, 541-543.
54. Komaritsa, I. D.; Plevachuk, N. E. Azolidones and their derivatives. II. Condensation of 4-imino-2-thiazolidones with aromatic aldehydes. Khimiya Geterotsiklicheskikh Soedinenii (Sbornik Serusoderzhashchie Geterotsikly), 1971, 3, 150-152. (In Russian)
55. Sheldrick, G. A short history of SHELX. Acta Cryst. Sect. A, 2008, 64, 112-122.
56. Farrugia, L. J. WinGX and ORTEP for Windows: an update. J. Appl. Cryst., 2012, 45, 849-854.
57. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst., 2009, 42, 229-341.
58. Spek, A. L. Structure validation in chemical crystallography. Acta Cryst. Sect. D, 2009, 65, 148-155.