Fused thiopyrano[2,3-d]thiazole derivatives as potential anticancer agents

Scientia Pharmaceutica

Volumn 80, Issue 3, 2012, Pages 509-529

  Kryshchyshyn, Anna ^a   Atamanyuk, Dmytro ^a,b   Lesyk, Roman ^a  

^a DANYLO HALYTSKY LVIV NATIONAL MEDICAL UNIVERSITY   (Ukraine)

^b MUTABILIS   (France)

Author keywords

Alkylation; Anticancer activity; COMPARE analysis; Cyanoethylation; Thiopyrano 2, 3 d 1, 3 thiazoles

Indexed keywords

ANTINEOPLASTIC AGENT; ETHYL REL 4[[(2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL)ACETYL]AMINO]BENZOATE; ETHYL REL[10 BROMO 2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETATE; ETHYL REL[2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETATE; REL 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H) YL] N [2 (TRIFLUOROMETHYL)PHENYL]ACETAMIDE; REL 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL] N [3 (TRIFLUOROMETHYL)PHENYL]ACETAMIDE; REL 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (2 METHOXYPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (2 METHYLPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (2,4 DICHLOROPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (3 METHOXYPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (3 METHYLPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (3,4 DICHLOROPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (4 ACETYLPHENYL) 2 [10 BROMO 2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (4 CHLOROPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (4 FLUOROPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (4 METHOXYPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (4 METHYLPHENYL) 2 [10 NITRO 2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; REL N (4 METHYLPHENYL) 2 [2 OXO 5A,11B DIHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 3(6H)YL]ACETAMIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA; LUNG NON SMALL CELL CANCER; MELANOMA; PROSTATE CANCER;

EID: 84866490988     PISSN: 00368709     EISSN: 22180532     Source Type: Journal    
DOI: 10.3797/scipharm.1204-02     Document Type: Article

References (27)

1. Kaminskyy DV, Lesyk RB. Structure-anticancer activity relationships among 4-azolidinone-3-carboxylic acids derivatives. Biopolym Cell. 2010; 26: 136-145.
2. Subtelna I, Atamanyuk D, Szymańska 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; 18: 5090-5102. http://dx.doi.org/10.1016/j.bmc.2010.05.073
3. Ead HA, Metwalli NH, Morsi NM. Cycloaddition reactions of 5-(2-thienyl)methylene derivatives of thiazolidinone-4-thiones and their antimicrobial activities. Arch Pharm Res. 1990; 13: 5-8. http://dx.doi.org/10.1007/BF02857825
4. Ead HA, Abdallah SO, Kassab NA, Metwalli NH, Saleh YE. 5-(Ethoxymethylene)thiazolidine-2,4-dione derivatives: reactions and biological activities. Arch Pharm. 1987; 320: 1227-1232. http://www.ncbi.nlm.nih.gov/pubmed/3439864
5. Kassab NA, Abdallah SO, Ead HA Reactions with 5-substituted-1,3-thiazolidine-2,4-dithiones heterodiene syntheses. Z Naturforsch. 1975; 30b: 441-445.
6. Lesyk RB, Zimenkovsky BS, Kaminskyy DV, Kryshchyshyn AP, Havryluk DYa, Atamanyuk DV, Subtel'Na IYu, Khyluk DV. Thiazolidinone motif in anticancer drug discovery. Experience of DH LNMU medicinal chemistry scientific group. Biopolym Cell. 2011; 27: 107-117.
7. Lesyk RB, Zimenkovsky BS. 4-Thiazolidones: Centenarian History, Current Status and Perspectives for Modern Organic and Medicinal Chemistry. Curr Org Chem. 2004; 8: 1547-1577. http://dx.doi.org/10.1002/chin.200506246
8. Kaminskyy DV, Zimenkovsky BS, Lesyk RB. Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivative. Eur J Med Chem. 2009; 44: 3627-3636. http://dx.doi.org/10.1016/j.ejmech.2009.02.023
9. 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. http://dx.doi.org/10.3797/scipharm.1109-14
10. 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. http://dx.doi.org/10.1016/j.bmc.2006.03.053
11. Matiychuk V, Lesyk R, Obushak M, Gzella A, Atamanyuk D, Ostapiuk Yu, Kryshchyshyn A. A new domino-Knoevenagel-hetero-Diels-Alder reaction. Tetrahedron Lett. 2008; 49: 4648-4651. http://dx.doi.org/10.1016/j.tetlet.2008.05.062
12. Atamanyuk D, Zimenkovsky B, Lesyk R. Synthesis and anticancer activity of novel thiopyrano[2,3-d]thiazole-based compounds containing norbornane moiety. J Sulf Chem. 2008; 29: 151-162. http://dx.doi.org/10.1080/17415990801911723
13. 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. http://dx.doi.org/10.1055/s-0030-1260765
14. Kryshchyshyn AP, Lesyk RB, Zimenkovsky BS. Synthesis and anticancer activity in vitro of isothiochromeno[3,4-d]thiazole derivarives. Ann Univ Mariae Curie Sklodowska. 2008; 21: 247-251. http://dx.doi.org/10.2478/v10080-008-0044-7
15. 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. http://dx.doi.org/10.1093/jnci/83.11.757
16. Boyd MR, Paull KD. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev Res. 1995; 34: 91-109. http://dx.doi.org/10.1002/ddr.430340203
17. Boyd MR. In: Cancer Drug Discovery and Development. Ed. Teicher BA, Volume 2. Totowa, NJ, USA: Humana Press, 1997: 23-43.
18. Shoemaker RH. The NCI60 human tumour cell line anticancer drug screen. Nat Rev Cancer. 2006; 6: 813-823. http://dx.doi.org/10.1038/nrc1951
19. Alley MC, Scudiero DA, Monks A, Hursey ML, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker RH, Boyd MR. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res.1988; 48: 589-601. http://www.ncbi.nlm.nih.gov/pubmed/3335022
20. Carter PH, Scherle PA, Muckelbauer JA, Voss ME, Liu RQ, Thompson LA, Tebben AJ, Solomon KA, Lo YC, Li Zh, Strzemienski P, Yang G, Falahatpisheh N, Xu M, Wu Zh, Farrow NA, Ramnarayan K, Wang J, Rideout D, Yalamoori V, Domaille P, Underwood DJ, Trzaskos JM, Friedman SM, Newton RC, Decicco CP. Photochemically enhanced binding of small molecules to the tumor necrosis factor receptor-1 inhibits the binding of TNF-α. Proc Natl Acad Sci U S A. 2001; 98: 11879-11886. http://dx.doi.org/10.1073/pnas.211178398
21. Grever MR, Schepartz SA, B.A. Chabner BA. The National Cancer Institute: cancer drug discovery and development program. Semin Oncol. 1992; 19: 622-638. http://www.ncbi.nlm.nih.gov/pubmed/1462164
22. Paull KD, Shoemaker RH, Hodes L, Monks A, Scudiero DA, Rubinstein L, Plowman J, Boyd MR. Display and analysis of patterns of differential activity of drugs against human tumor cell lines: development of mean graph and COMPARE algorithm. J Natl Cancer Inst. 1989; 81: 1088-1092. http://dx.doi.org/10.1093/jnci/81.14.1088
23. Paull KD, Lin CM, Malspeis L, Hamel E. Identification of novel antimitotic agents acting at the tubulin level by computer-assisted evaluation of differential cytotoxicity data. Cancer Res. 1992; 52: 3892-3900. http://www.ncbi.nlm.nih.gov/pubmed/1617665
24. Zaharevitz DW, Holbeck SL, Bowerman Ch, Svetlik PA. COMPARE: a web accessible tool for investigating mechanisms of cell growth inhibition. J Mol Graphics Modell. 2002; 20: 297-303. http://dx.doi.org/10.1016/S1093-3263(01)00126-7
25. Holbeck SL. Update on NCI in vitro drug screen utilities. Eur J Cancer. 2004; 40: 785-793. http://dx.doi.org/10.1016/j.ejca.2003.11.022
26. Bohen SP. Genetic and Biochemical Analysis of p23 and Ansamycin Antibiotics in the Function of Hsp90-Dependent Signaling Proteins. Mol Cell Biol. 1998; 18: 3330-3339. http://www.ncbi.nlm.nih.gov/pubmed/9584173
27. Zhao Y, Li X, Sun Y, Niu W, Hu Z, Lin L, Kong Q-Zh. MMPT: a thiazolidine compound inhibits the growth of lung cancer H1792 cells via Fas-mediated and caspase-dependent apoptosis pathway. Invest New Drugs. 2010; 28: 318-325. http://dx.doi.org/10.1007/s10637-009-9259-z