Combretastatin A-4 derivatives: Synthesis and evaluation of 2,4,5-triaryl-1H-imidazoles as potential agents against H1299 (non-small cell lung cancer cell)

Molecular Diversity

Volumn 16, Issue 4, 2012, Pages 697-709

  Tseng, Chih Hua ^a   Li, Chi Yi ^a   Chiu, Chien Chih ^a   Hu, Huei Ting ^a   Han, Chein Hwa ^b   Chen, Yeh Long ^a   Tzeng, Cherng Chyi ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b CHIA NAN UNIVERSITY OF PHARMACY AND SCIENCE   (Taiwan)

Author keywords

Cell cycle; Combretastatin A 4 (CA 4); Cytotoxicity; H1299; Triarylimidazoles

Indexed keywords

2 (4' BROMOPHENYL) 4,5 BIS[4 [2 (PYRROLIDIN 1 YL)ETHOXY]PHENYL] 1H IMIDAZOLE; 2 (4' BROMOPHENYL) 4,5 BIS[4 [3 (DIMETHYLAMINO)PROPOXY]PHENYL] 1H IMIDAZOLE; 2 (4' METHOXYPHENYL) 4,5 BIS[4 [2 (PYRROLIDIN 1 YL)ETHOXY]PHENYL] 1H IMIDAZOLE; 2 (4' METHOXYPHENYL) 4,5 BIS[4 [3 (DIMETHYLAMINO)PROPOXY]PHENYL] 1H IMIDAZOLE; 2 (5' BROMOFURAN 2' YL) 4,5 BIS(4 METHOXYPHENYL) 1H IMIDAZOLE; 2 (5' NITROFURAN 2' YL) 4,5 BIS [4 [2 (PYRROLIDIN 1 YL)ETHOXY]PHENYL] 1H IMIDAZOLE; 2 (FURAN 2 YL) 4,5 BIS[4 [3 (DIMETHYLAMINO)PROPOXY]PHENYL] 1H IMIDAZOLE; 2 (FURAN 2' YL) 4,5 BIS(4 METHOXYPHENYL) 1H IMIDAZOLE; 2 (FURAN 2' YL) 4,5 BIS[4 [2 (PYRROLIDIN 1YL)ETHOXY]PHENYL] 1H IMIDAZOLE; 2 [4' (TRIFLUOROMETHYL)PHENYL] 4,5 BIS[4 [3 (DIMETHYLAMINO)PROPOXY]PHENYL] 1H IMIDAZOLE; 2 PHENYL 4,5 BIS[4 [2 (PYRROLIDIN 1 YL)ETHOXY]PHENYL] 1H IMIDAZOLE; 4,4 [2 (4' BROMOPHENYL) 1H IMIDAZOLE 4,5 DIYL]DIPHENOL; 4,4 [2 (4' METHOXYPHENYL) 1H IMIDAZOLE 4,5 DIYL]DIPHENOL; 4,4 [2 (5' BROMOFURAN 2' YL) 1H IMIDAZOLE 4,5 DIYL]DIPHENOL; 4,4 [2 (5' NITROFURAN 2' YL) 1H IMIDAZOLE 4,5 DIYL]DIPHENOL; 4,4 [2 (FURAN 2' YL) 1H IMIDAZOLE 4,5 DIYL]DIPHENOL; 4,4 [2 [4' (TRIFLUOROMETHYL)PHENYL] 1H IMIDAZOLE 4,5 DIYL]DIPHENOL; 4,5 BIS(4 METHOXYPHENYL) 2 (5' NITROFURAN 2' YL) 1H IMIDAZOLE; 4,5 BIS(4 METHOXYPHENYL) 2 [4' (TRIFLUOROMETHYL)PHENYL] 1H IMIDAZOLE; 4,5 BIS[4 [2 (PYRROLIDIN 1 YL)ETHOXY]PHENYL] 2 [4' (TRIFLUOROMETHYL)PHENYL] 1H IMIDAZOLE; 4,5 BIS[4 [3 (DIMETHYLAMINO)PROPOXY]PHENYL] 2 (5 NITROFURAN 2 YL) 1H IMIDAZOLE; 4,5 BIS[4 [3 (DIMETHYLAMINO)PROPOXY]PHENYL] 2 PHENYL 1H IMIDAZOLE; ANTINEOPLASTIC AGENT; COMBRETASTATIN A4; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG; COMBRETASTATIN A4 PHOSPHATE; STILBENE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; FETUS LUNG; HUMAN; HUMAN CELL; IN VITRO STUDY; LUNG SMALL CELL CANCER; PRIORITY JOURNAL; APOPTOSIS; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; IMMUNOBLOTTING; LUNG NON SMALL CELL CANCER; METHODOLOGY; PATHOLOGY; SYNTHESIS; TRANSITION TEMPERATURE; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CARCINOMA, NON-SMALL-CELL LUNG; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IMIDAZOLES; IMMUNOBLOTTING; STILBENES; TRANSITION TEMPERATURE;

EID: 84878023932     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-012-9396-8     Document Type: Article

References (36)

1. Shustik C, Dalton W, Gros P (1995) P-glycoprotein-mediated multidrug resistance in tumor cells: biochemistry, clinical relevance and modulation. Mol Aspects Med 16: 1-78. doi: 10.1016/0098-2997(94)00040-A
2. Fardel O, Lecureur V, Guillouzo A (1996) The P-glycoprotein multidrug transporter. Gen Pharmacol 27: 1283-1291. doi: 10.1016/S0306-3623(96)00081-X (Pubitemid 26419684)
3. Pettit GR, Toki BE, Herald DL, Boyd MR, Hamel E, Pettit RK, Chapuis JC (1999) Antineoplastic Agents. 410. Asymmetric hydroxylation of trans-combretastatin A-4. J Med Chem 42: 1459-1465. doi: 10.1021/jm9807149 (Pubitemid 29200882)
4. Pettit GR, Rhodes MR, Herald DL, Chaplin DJ, Stratford MR, Hamel E, Pettit RK, Chapuis JC, Oliva D (1998) Antineoplastic agents. 393. Synthesis of the trans isomer of combretastatin A-4 prodrug. Anti-Cancer Drug Des 13: 981-993 (Pubitemid 29178769)
5. Bedford SB, Quarterman CP, Rathbone DL, Slack JA, Griffin RJ, Stevens MFG (1996) Synthesis of water-soluble prodrugs of the cytotoxic agent combretastatin A4. Bioorg Med Chem Lett 6: 157-160. doi: 10.1016/0960-894X(95) 00580-M (Pubitemid 26048659)
6. Ohsumi K, Nakagawa R, Fukuda Y, Hatanaka T, Morinaga Y, Nihei Y, Ohishi K, Suga Y, Akiyama Y, Tsuji T (1998) Novel combretastatin analogues effective against murine solid tumors: design and structure-Activity relationships. J Med Chem 41: 3022. doi: 10.1021/jm980101w (Pubitemid 28359938)
7. Shirai R, Takayama H, Nishikawa A, Koiso Y, Hashimoto Y (1998) Asymmetric synthesis of antimitotic combretadioxolane with potent antitumor activity against multi-drug resistant cells. Bioorg Med Chem Lett 8: 1997-2000. doi: 10.1016/S0960-894X(98)00344-8 (Pubitemid 28372477)
8. Ohsumi K, Hatanaka T, Fujita K, Nakagawa R, Fukuda Y, Niher Y, Suga Y, Morinaga Y, Akiyama Y, Tsuji T (1998) Syntheses and antitumor activity of cis-restricted combretastatins: five-membered heterocyclic analogues. Bioorg Med Chem Lett 8: 3153-3158. doi: 10.1016/S0960-894X(98)00579-4 (Pubitemid 28551638)
9. Medarde M, Ramos AC, Caballero E, Peláez-Lamamiéde Clairac R, López JL, Grávalos DG, Feliciano AS (1999) Synthesis and pharmacological activity of diarylindole derivatives: cytotoxic agents based on combretastatins. Bioorg Med Chem Lett 9: 2303-2308. doi: 10.1016/S0960-894X(99) 00370-4 (Pubitemid 29391511)
10. Wang L, Woods KW, Li Q, Barr KJ, McCroskey RW, Hannick SM, Gherke L, Credo RB, Hui YH, Marsh K, Warner R, Lee JY, Zielinski-Mozng N, Frost D, Rosenberg SH, Sham HL (2002) Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-Activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. J Med Chem 45: 1697-1711. doi: 10.1021/jm010523x (Pubitemid 34293536)
11. Tron GC, Pagliai F, Del Grosso E, Genazzani AA, Sorba G (2005) Synthesis and cytotoxic evaluation of combretafurazans. J Med Chem 48: 3260-3268. doi: 10.1021/jm049096o (Pubitemid 40628046)
12. Pirali T, Busacca S, Beltrami L, Imovilli D, Pagliai F, Miglio G, Massarotti A, Verotta L, Tron GC, Sorba G, Genazzani AA (2006) Synthesis and cytotoxic evaluation of combretafurans, potential scaffolds for dual-Action antitumoral agents. J Med Chem 49: 5372-5376. doi: 10.1021/jm060621o (Pubitemid 44260231)
13. Abu Thaher B, Koch P, Schattel V, Laufer S (2009) Role of the hydrogen bonding heteroatom-Lys53 interaction between the p38 alpha mitogen-Activated protein (MAP) kinase and pyridinyl-substituted 5-membered heterocyclic ring inhibitors. J Med Chem 52: 2613-2617. doi: 10.1021/jm801467h
14. Bracht C, Hauser DR, Schattel V, Albrecht W, Laufer SA (2010) Synthesis and biological testing of N-Aminoimidazole-based p38alpha MAP kinase inhibitors. ChemMedChem 5: 1134-1142. doi: 10.1002/cmdc.201000114
15. Abu Thaher B, Arnsmann M, Totzke F, Ehlert JE, Kubbutat MH, Schächtele C, Zimmermann MO, Koch P, Boeckler FM, Laufer SA (2012) Tri- and tetrasubstituted pyrazole derivates: regioisomerism switches activity from p38MAP kinase to important cancer kinases. J Med Chem 55: 961-965. doi: 10.1021/jm201391u
16. Tseng CH, Chen YL, Chung KY, Wang CH, Peng SI, Cheng CM, Tzeng CC (2011) Synthesis and antiproliferative evaluation of 2,3-diarylquinoline derivatives. Org Biomol Chem 9: 3205-3216. doi: 10.1039/C0OB01225D
17. Bedeschi A, Zarini F, Cabri W, Candiani I, Penco S, Capolongo L, Ciomei M, Farao M, Grandi M (1996) Synthesis and antitumor activity of a new class of water soluble camptothecin derivatives. Bioorg Med Chem Lett 6: 671-674. doi: 10.1016/0960-894X(96)00083-2 (Pubitemid 26107898)
18. Schmid B, Chung DE, Warnecke A, Fichtner I, Kratz F (2007) Albumin-binding prodrugs of camptothecin and doxorubicin with an Ala-Leu-Ala-Leu-linker that are cleaved by cathepsin B: synthesis and antitumor efficacy. Bioconj Chem 18: 702-716. doi: 10.1021/bc0602735 (Pubitemid 47010789)
19. Ishii M, Iwahana M, Mitsui I, Minami M, Imagawa S, Tohgo A, Ejima A (2000) Growth inhibitory effect of a new camptothecin analog, DX-8951f, on various drug-resistant sublines including BCRP-mediated camptothecin derivative-resistant variants derived from the human lung cancer cell line PC-6. Anti-cancer drugs 11: 353-362 (Pubitemid 30459470)
20. Kim YY, Park CK, Kim SK, Phi JH, Kim JH, Kim CY, Wang KC, Cho BK (2009) CKD-602, a camptothecin derivative, inhibits proliferation and induces apoptosis in glioma cell lines. Oncol Rep 21: 1413-1419. doi: 10.3892/or-00000369
21. Pettit GR, Cragg GM, Herald DL, Schmidt JM, Lobavanijaya P (1982) Anti-neoplastic agents. 84. Isolation and structure of combretastatin. Can J Chem 60: 1347-1376
22. Chen YW, Chen YL, Tseng CH, Liang CC, Yang CN, Yao YC, Lu PJ, Tzeng CC (2011) Discovery of 4-Anilinofuro[2,3-b]quinoline derivatives as selective and orally active compounds against non-small-cell lung cancers. J Med Chem 54: 4446-4461. doi: 10.1021/jm200046z
23. Cheng SH, Chen CM, Jian JJ, Tsai SY, Liu WT, Liu MC, Chen CM, Lin HH (1996) Breast-conserving surgery and radiotherapy for early breast cancer in Taiwan. J Formos Med Assoc 95: 372-377 (Pubitemid 126700333)
24. Lu YS, Kuo SH, Huang CS (2004) Recent advances in the management of primary breast cancers. J Formos Med Assoc 103: 579-598
25. Ko YC, Wang JL, Wu CC, Huang WT, Lin MC (2005) Lung cancer at a medical center in southern Taiwan. Chang Gung Med J 28: 387-395
26. Chien CR, Tsai CM, Tang ST, Chung KP, Chiu CH, Lai MS s (2008) Quality of care for lung cancer in Taiwan: a pattern of care based on core measures in the Taiwan cancer database registry. J Formos Med Assoc 107: 635-643. doi: 10.1016/S0929-6646(08)60181-3
27. Kuo YH, Lin ZZ, Yang YY, Shao YY, Shau WY, Kuo RN, Yang JC, Lai MS (2012) Survival of patients with small cell lung carcinoma in Taiwan. Oncology 82: 19-24. doi: 10.1159/000335084
28. 2 B monomers. Macromolecules 38: 297-306. doi: 10.1021/ma0489467 (Pubitemid 40184303)
29. Tseng CH, Lin CS, Shih PK, Tsao LT, Wang JP, Cheng CM, Tzeng CC, Chen YL (2009) Furo[3′,2′:3,4]naphtho[1,2-d] imidazole derivatives as potential inhibitors of inflammatory factors in sepsis. Bioorg Med Chem 17: 6773-6779. doi: 10.1016/j.bmc.2009.07.054
30. 2 synthase-1 (mPGES-1). Mol Divers 16: 2153-2229. doi: 10.1007/s11030-011-9347-9
31. Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao Z, Lindsley CW (2004) Efficient synthesis of imidazoles from aldehydes and 1,2-diketones using microwave irradiation. Org Lett 6: 1453-1456. doi: 10.1021/ol049682b (Pubitemid 38626327)
32. Antolini M, Bozzoli A, Ghiron C, Kennedy G, Rossi T, Ursini A (1999) Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. Bioorg Med Chem Lett 9: 1023-1028. doi: 10.1016/S0960-894X(99)00112-2 (Pubitemid 29179901)
33. Ota H, Tokunaga E, Chang K, Hikasa M, Iijima K, Eto M, Kozaki K, Akishita M, Ouchi Y, Kaneki M (2006) Sirt1 inhibitor, Sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells. Oncogene 25: 176-185. doi: 10.1038/sj.onc.1209049 (Pubitemid 43083679)
34. Wada T, Penninger JM (2004) Mitogen-Activated protein kinases in apoptosis regulation. Oncogene 23: 2838-2849. doi: 10.1038/sj.onc.1207556 (Pubitemid 38638846)
35. Altieri DC (2008) Survivin, cancer networks and pathway-directed drug discovery. Nat Rev Cancer 8: 61-70. doi: 10.1038/nrc2293
36. Roehm NW, Rodgers GH, Hatfield SM, Glasebrook AL (1991) An improved colorimetric assay for cell proliferation and viability utilizing the tetrazolium salt XTT. J Immunol Methods 142: 257-265. doi: 10.1016/0022-1759(91) 90114-U