Synthesis and antitumour evaluation of novel 2-phenylbenzimidazoles

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 23, Issue 5, 2008, Pages 641-647

  Kadri, Hachemi ^a   Matthews, Charles S ^b   Bradshaw, Tracey D ^b   Stevens, Malcolm F G ^b   Westwell, Andrew D ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Antitumour; Benzimidazoles; Fluorination; Synthesis

Indexed keywords

1 METHYL 2 (3,4,5 TRIMETHOXYPHENYL) 1H BENZIMIDAZOLE; 2 (3,4 DIMETHOXYPHENYL) 1 METHYL 1H BENZIMIDAZOLE; 2 (3,4 DIMETHOXYPHENYL) 1H BENZIMIDAZOLE; 2 (3,4 DIMETHOXYPHENYL) 5 FLUORO 1 TOLUENESULFONYL 1H BENZIMIDAZOLE; 2 (3,4 DIMETHOXYPHENYL) 5 FLUORO 1H BENZIMIDAZOLE; 2 (3,4 DIMETHOXYPHENYL) 5 FLUOROBENZOTHIAZOLE; 2 (3,4 DIMETHOXYPHENYL) 6 FLUORO 1 TOLUENESULFONYL 1H BENZIMIDAZOLE; 2 (3,4,5 TRIMETHOXYPHENYL) 1H BENZIMIDAZOLE; 2 (BENZO[1,3]DIOXOL 5 YL) 1 METHYL 1H BENZIMIDAZOLE; 2 (BENZO[1,3]DIOXOL 5 YL) 1H BENZIMIDAZOLE; 2 (BENZO[1,3]DIOXOL 5 YL) 5 FLUORO 1H BENZIMIDAZOLE; 5 FLUORO 2 (3,4,5 TRIMETHOXYPHENYL) 1H BENZIMIDAZOLE; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; PHENZIDOLE DERIVATIVE; PMX 610; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CELL STRAIN MCF 7; CONTROLLED STUDY; DERIVATIZATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; HYPOTHESIS; IN VITRO STUDY; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; BREAST NEOPLASMS; CELL LINE, TUMOR; FEMALE; HUMANS; HYDROCARBONS, FLUORINATED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 53249101414     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360802205398     Document Type: Article

References (16)

1. Boiani, M. and Gonzalez, M. (2005) Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini Rev Med Chem, 5, pp. 409-424.
2. Lansing, TJ, McConnell, RT, Duckett, DR, Spehar, GM, Knick, VB, Hassler, DF, Noro, N., Furuta, M., Emmitte, KA, Gilmer, TM, Mook Jr, RA and Cheung, M. (2007) In vitro biological activity of a novel small-molecule inhibitor of polo-like kinase 1. Mol Cancer Therap, 6, pp. 450-459.
3. White, AW, Curtin, NJ, Eastman, BW, Golding, BT, Hostomsky, Z., Kyle, S., Li, J., Maegley, KA, Skalitzky, DJ, Webber, SE, Yu, XH and Griffin, RJ (2004) Potentiation of cytotoxic drug activity in human tumour cell lines, by amino-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors. Bioorg Med Chem Lett, 14, pp. 2433-2437.
4. Berry, JM, Bradshaw, TD, Fichtner, I., Ren, R., Schwalbe, CH, Wells, G., Chew, E-H, Stevens, MFG and Westwell, AD (2005) Quinols as novel therapeutic agents. 2. 4-(1-arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2,5-dien-1-ones and related agents as potent and selective antitumor agents. J Med Chem, 48, pp. 639-644.
5. Bradshaw, TD and Westwell, AD (2004) The development of the antitumour benzothiazole prodrug, Phortress, as a clinical candidate. Curr Med Chem, 11, pp. 1241-1253.
6. Bradshaw, TD, Stevens, MFG and Westwell, AD (2001) The discovery of the potent and selective antitumour agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203) and related compounds. Curr Med Chem, 8, pp. 203-210.
7. Shah, P. and Westwell, AD (2007) The role of fluorine in medicinal chemistry. J Enz Inhib Med Chem, 22, pp. 527-540.
8. Hutchinson, I., Chua, M-S, Browne, H., Trapani, V., Fichtner, I., Bradshaw, TD, Westwell, AD and Stevens, MFG (2001) Antitumor benzothiazoles. 14. The synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles. J Med Chem, 44, pp. 1446-1455.
9. Kashiyama, E., Hutchinson, I., Chua, M-S, Stinson, SF, Phillips, LR, Kaur, G., Sausville, EA, Bradshaw, TD, Westwell, AD and Stevens, MFG (1999) Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N- oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles. J Med Chem, 42, pp. 4172-4184.
10. Hutchinson, I., Jennings, SA, Vishnuvajjala, BR, Westwell, AD and Stevens, MFG (2002) Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs. J Med Chem, 45, pp. 744-747.
11. Mortimer, CG, Wells, G., Crochard, J-P, Stone, EL, Bradshaw, TD, Stevens, MFG and Westwell, AD (2006) Antitumor benzothiazoles. 26. 2-(3,4-Dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines. J Med Chem, 49, pp. 179-185.
12. Brantley, E., Trapani, V., Alley, MC, Hose, CD, Bradshaw, TD, Stevens, MFG, Sausville, EA and Stinson, SF (2004) Fluorinated 2-(4-amino-3-methylphenyl)benzothiazoles induce CYP1A1 expression, become metabolized, and bind to macromolecules in sensitive human cancer cells. Drug Metab Dispos, 32, pp. 1392-1401.
13. Chua, M-S, Kashiyama, E., Bradshaw, TD, Stinson, SF, Brantley, E., Sausville, EA and Stevens, MFG (2000) Role of CYP1A1 in modulation of antitumor properties of the novel agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203, NSC 674495) in human breast cancer cells. Cancer Res, 60, pp. 5196-5203.
14. Ghose, AK and Crippen, GM (1987) Atomic physicochemical parameters for 3-dimensional structure-activity-directed quantitative structure-activity relationships. 2. Modeling dispersive and hydrophobic interactions. J Chem Inf Comp Sci, 27, pp. 21-35.
15. Grimmet, MR (1984) Imidazoles and their benzo derivatives. Comprehensive heterocyclic chemistry, 5, p. 457. Pergamon, Oxford
16. Chew, E-H, Matthews, CS, Zhang, J., McCarroll, AJ, Hagen, T., Stevens, MFG, Westwell, AD and Bradshaw, TD (2006) Antitumor quinols: Role of glutathione in modulating quinol-induced apoptosis and identification of putative cellular protein targets. Biochem Biophys Res Comm, 346, pp. 242-251.