Design, synthesis and biological evaluation of novel diphenylthiazole-based cyclooxygenase inhibitors as potential anticancer agents

Bioorganic Chemistry

Volumn 57, Issue , 2014, Pages 132-141

  Abdelazeem, Ahmed H ^a,c   Gouda, Ahmed M ^b,c   Omar, Hany A ^a,c   Tolba, Mai F ^d  

^a TAIF UNIVERSITY   (Saudi Arabia)

^b UMM AL QURA UNIVERSITY   (Saudi Arabia)

^c Beni Suef University   (Egypt)

^d Ain Shams University   (Egypt)

Author keywords

Anticancer; COX; Diphenylthiazole; Docking; NSAIDs; Thiazolidinone

Indexed keywords

2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO) 5 (4 METHOXYBENZYLIDENE)THIAZOLIDIN 4 ONE; 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO] 5 (3 NITROBENZYLIDENE)THIAZOLIDIN 4 ONE; 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO] 5 (4 HYDROXY3 METHOXYBENZYLIDENE)THIAZOLIDIN 4 ONE; 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO] 5 (4 METHYLBENZYLIDENE)THIAZOLIDIN 4 ONE; 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO] 5 (4 NITROBENZYLIDENE)THIAZOLIDIN 4 ONE; 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO] 5 (NAPHTHALEN 1 YLMETHYLENE)THIAZOLIDIN 4 ONE; 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO] 5 (PYRIDIN 4 YLMETHYLENE)THIAZOLIDIN 4 ONE; 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO]THIAZOLIDIN 4 ONE; 4 [2 [(4 OXOTHIAZOLIDIN 2 YLIDENE)AMINO] 4 PHENYLTHIAZOL 5 YL]BENZENESULFONAMIDE; 4 [2 [(5 BENZYLIDENE 4 OXOTHIAZOLIDIN 2 YLIDENE)AMINO] 4 PHENYLTHIAZOL 5 YL]BENZENESULFONAMIDE; 4 [2 [[ 5 (NAPHTHALEN 1 YLMETHYLENE) 4 OXOTHIAZOLIDIN 2 YLIDENE]AMINO] 4 PHEMYLTHIAZOL 5 YL]BENZENESULFONAMIDE; 5 (4 CHLOROBENZYLIDENE) 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO]THIAZOLIDIN 4 ONE; 5 BENZYLIDENE 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO]THIAZOLIDIN 4 ONE; 5 [4 (DIMETHYLAMINO)BENZYLIDENE] 2 [(4,5 DIPHENYLTHIAZOL 2 YL)IMINO]THIAZOLIDIN 4 ONE; ANTINEOPLASTIC AGENT; CELECOXIB; CYCLOOXYGENASE 2; DOXORUBICIN; PROSTAGLANDIN SYNTHASE INHIBITOR; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; PROSTAGLANDIN SYNTHASE;

ANGIOGENESIS; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BINDING SITE; CANCER CELL LINE; CANCER MORTALITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC50; MOLECULAR DOCKING; PRIORITY JOURNAL; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; METABOLISM; NEOPLASMS; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CYCLOOXYGENASE INHIBITORS; DRUG DESIGN; HUMANS; MOLECULAR DOCKING SIMULATION; NEOPLASMS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; THIAZOLES;

EID: 84934288431     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2014.10.001     Document Type: Article

References (39)

1. [1] Chan, T.A., Lancet Oncol. 3 (2002), 166–174.
2. [2] Thun, M.J., Henley, S.J., Patrono, C., J. Natl. Cancer Inst. 94 (2002), 252–266.
3. [3] Gasparini, G., Longo, R., Sarmiento, R., Morabito, A., Lancet Oncol. 4 (2003), 605–615.
4. [4] Mazhar, D., Gillmore, R., Waxman, J., QJM 98 (2005), 711–718.
5. [5] Zhang, L., Yu, J., Park, B.H., Kinzler, K.W., Vogelstein, B., Science 290 (2000), 989–992.
6. [6] Leahy, K.M., Ornberg, R.L., Wang, Y., Zweifel, B.S., Koki, A.T., Masferrer, J.L., Cancer Res. 62 (2002), 625–631.
7. [7] Rigas, B., Kashfi, K., J. Pharmacol. Exp. Ther. 314 (2005), 1–8.
8. [8] Sarkar, F.H., Adsule, S., Li, Y., Padhye, S., Med. Chem. 7 (2007), 599–608.
9. [9] Arico, S., Pattingre, S., Bauvy, C., Gane, P., Barbat, A., Codogno, P., Ogier-Denis, E., J. Biol. Chem. 277 (2002), 27613–27621.
10. [10] Bertagnolli, M.M., Eagle, C.J., Zauber, A.G., Redston, M., Solomon, S.D., Kim, K., Tang, J., Rosenstein, R.B., Wittes, J., Corle, D., Hess, T.M., Woloj, G.M., Boisserie, F., Anderson, W.F., Viner, J.L., Bagheri, D., Burn, J., Chung, D.C., Dewar, T., Foley, T.R., Hoffman, N., Macrae, F., Pruitt, R.E., Saltzman, J.R., Salzberg, B., Sylwestrowicz, T., Gordon, G.B., Hawk, E.T., N. Engl. J. Med. 355 (2006), 873–884.
11. [11] Hawcroft, G., D'Amico, M., Albanese, C., Markham, A.F., Pestell, R.G., Hull, M.A., Carcinogenesis 23 (2002), 107–114.
12. [12] Jones, M.K., Wang, H., Peskar, B.M., Levin, E., Itani, R.M., Sarfeh, I.J., Tarnawski, A.S., Nat. Med. 5 (1999), 1418–1423.
13. [13] Dadiboyena, S., Nefzi, A., Eur. J. Med. Chem. 45 (2010), 4697–4707.
14. [14] Carter, J.S., Kramer, S., Talley, J.J., Penning, T., Collins, P., Graneto, M.J., Seibert, K., Koboldt, C.M., Masferrer, J., Zweifel, B., Bioorg. Med. Chem. Lett. 9 (1999), 1171–1174.
15. [15] Havrylyuk, D., Zimenkovsky, B., Lesyk, R., Phosphorus Sulfur Silicon Rel. Elem. 184 (2009), 638–650.
16. [16] Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Zaprutko, L., Gzella, A., Lesyk, R., Eur. J. Med. Chem. 44 (2009), 1396–1404.
17. [17] Lesyk, R.B., Zimenkovsky, B.S., Curr. Org. Chem. 8 (2004), 1547–1577.
18. [18] Knight, S.D., Adams, N.D., Burgess, J.L., Chaudhari, A.M., Darcy, M.G., Donatelli, C.A., Luengo, J.I., Newlander, K.A., Parrish, C.A., Ridgers, L.H., Sarpong, M.A., Schmidt, S.J., Van Aller, G.S., Carson, J.D., Diamond, M.A., Elkins, P.A., Gardiner, C.M., Garver, E., Gilbert, S.A., Gontarek, R.R., Jackson, J.R., Kershner, K.L., Luo, L., Raha, K., Sherk, C.S., Sung, C.-M., Sutton, D., Tummino, P.J., Wegrzyn, R.J., Auger, K.R., Dhanak, D., ACS Med. Chem. Lett. 1 (2010), 39–43.
19. [19] Havrylyuk, D., Mosula, L., Zimenkovsky, B., Vasylenko, O., Gzella, A., Lesyk, R., Eur. J. Med. Chem. 45 (2010), 5012–5021.
20. [20] Carter, P.H., Scherle, P.A., Muckelbauer, J.K., Voss, M.E., Liu, R.Q., Thompson, L.A., Tebben, A.J., Solomon, K.A., Lo, Y.C., Li, Z., Strzemienski, P., Yang, G., Falahatpisheh, N., Xu, M., Wu, Z., Farrow, N.A., Ramnarayan, K., Wang, J., Rideout, D., Yalamoori, V., Domaille, P., Underwood, D.J., Trzaskos, J.M., Friedman, S.M., Newton, R.C., Decicco, C.P., Proc. Natl. Acad. Sci. USA 98:2001 (1884), 11879–11884.
21. [21] Degterev, A., Lugovskoy, A., Cardone, M., Mulley, B., Wagner, G., Mitchison, T., Yuan, J., Nat. Cell Biol. 3 (2001), 173–182.
22. [22] Ahn, J.H., Kim, S.J., Park, W.S., Cho, S.Y., Ha, J.D., Kim, S.S., Kang, S.K., Jeong, D.G., Jung, S.K., Lee, S.H., Kim, H.M., Park, S.K., Lee, K.H., Lee, C.W., Ryu, S.E., Choi, J.K., Bioorg. Med. Chem. Lett. 16 (2006), 2996–2999.
23. [23] Cutshall, N.S., O'Day, C., Prezhdo, M., Bioorg. Med. Chem. Lett. 15 (2005), 3374–3379.
24. [24] Geronikaki, A., Eleftheriou, P., Vicini, P., Alam, I., Dixit, A., Saxena, A.K., J. Med. Chem. 51 (2008), 5221–5228.
25. [25] Dayam, R., Aiello, F., Deng, J., Wu, Y., Garofalo, A., Chen, X., Neamati, N., J. Med. Chem. 49 (2006), 4526–4534.
26. [26] Ren, J., Wang, S.-M., Wu, L.-F., Xu, Z.-X., Dong, B.-H., Dyes Pigments 76 (2008), 310–314.
27. [27] Vicini, P., Geronikaki, A., Incerti, M., Zani, F., Dearden, J., Hewitt, M., Bioorg. Med. Chem. 16 (2008), 3714–3724.
28. [28] Momose, Y., Meguro, K., Ikeda, H., Hatanaka, C., Oi, S., Sohda, T., Chem. Pharm. Bull. (Tokyo). 39 (1991), 1440–1445.
29. [29] Lesyk, R., Vladzimirska, O., Holota, S., Zaprutko, L., Gzella, A., Eur. J. Med. Chem. 42 (2007), 641–648.
30. [30] Kaminskyy, D., Zimenkovsky, B., Lesyk, R., Eur. J. Med. Chem. 44 (2009), 3627–3636.
31. [31] Pommery, N., Taverne, T., Telliez, A., Goossens, L., Charlier, C., Pommery, J., Goossens, J.F., Houssin, R., Durant, F., Henichart, J.P., J. Med. Chem. 47 (2004), 6195–6206.
32. [32] Khan, M.N., Lee, Y.S., Med. Res. Rev. 31 (2011), 161–201.
33. [33] Boland, G.P., Butt, I.S., Prasad, R., Knox, W.F., Bundred, N.J., Br. J. Cancer 90 (2004), 423–429.
34. [34] Kurumbail, R.G., Stevens, A.M., Gierse, J.K., McDonald, J.J., Stegeman, R.A., Pak, J.Y., Gildehaus, D., Miyashiro, J.M., Penning, T.D., Seibert, K., Isakson, P.C., Stallings, W.C., Nature 384 (1996), 644–648.
35. [35] Accelrys Software Inc., Discovery Studio Modeling Environment, Release 2.5. San Diego: Accelrys Software Inc., 2007.
36. [36] Kulkarni, R.A., Thaker, S.R., J. Indian Chem. Soc. 65 (1988), 432–434.
37. [37] Arafa el, S.A., Abdelazeem, A.H., Arab, H.H., Omar, H.A., Acta Pharmacol. Sin. 35 (2014), 394–400.
38. [38] Omar, H.A., Arafa el, S.A., Salama, S.A., Arab, H.H., Wu, C.H., Weng, J.R., Toxicol. Appl. Pharmacol. 272 (2013), 616–624.
39. [39] Bhatia, N.M., Mahadik, K.R., Bhatia, M.S., Daru 18 (2010), 230–236.