1,227
Views
20
CrossRef citations to date
0
Altmetric
Research Article

Synthesis and antitumour evaluation of novel 2-phenylbenzimidazoles

, , , &
Pages 641-647 | Received 20 Dec 2007, Accepted 07 May 2008, Published online: 20 Oct 2008

References

  • M Boiani, and M Gonzalez. (2005). Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini Rev Med Chem 5:409–424.
  • TJ Lansing, RT McConnell, DR Duckett, GM Spehar, VB Knick, DF Hassler, N Noro, M Furuta, KA Emmitte, TM Gilmer, RA MookJr, and M Cheung. (2007). In vitro biological activity of a novel small-molecule inhibitor of polo-like kinase 1. Mol Cancer Therap 6:450–459.
  • AW White, NJ Curtin, BW Eastman, BT Golding, Z Hostomsky, S Kyle, J Li, KA Maegley, DJ Skalitzky, SE Webber, XH Yu, and RJ Griffin. (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 14:2433–2437.
  • JM Berry, TD Bradshaw, I Fichtner, R Ren, CH Schwalbe, G Wells, E-H Chew, MFG Stevens, and AD Westwell. (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 48:639–644.
  • TD Bradshaw, and AD Westwell. (2004). The development of the antitumour benzothiazole prodrug, Phortress, as a clinical candidate. Curr Med Chem 11:1241–1253.
  • TD Bradshaw, MFG Stevens, and AD Westwell. (2001). The discovery of the potent and selective antitumour agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203) and related compounds. Curr Med Chem 8:203–210.
  • P Shah, and AD Westwell. (2007). The role of fluorine in medicinal chemistry. J Enz Inhib Med Chem 22:527–540.
  • I Hutchinson, M-S Chua, H Browne, V Trapani, I Fichtner, TD Bradshaw, AD Westwell, and MFG Stevens. (2001). Antitumor benzothiazoles. 14. The synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles. J Med Chem 44:1446–1455.
  • E Kashiyama, I Hutchinson, M-S Chua, SF Stinson, LR Phillips, G Kaur, EA Sausville, TD Bradshaw, AD Westwell, and MFG Stevens. (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 42:4172–4184.
  • I Hutchinson, SA Jennings, BR Vishnuvajjala, AD Westwell, and MFG Stevens. (2002). Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs. J Med Chem 45:744–747.
  • CG Mortimer, G Wells, J-P Crochard, EL Stone, TD Bradshaw, MFG Stevens, and AD Westwell. (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 49:179–185.
  • E Brantley, V Trapani, MC Alley, CD Hose, TD Bradshaw, MFG Stevens, EA Sausville, and SF Stinson. (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 32:1392–1401.
  • M-S Chua, E Kashiyama, TD Bradshaw, SF Stinson, E Brantley, EA Sausville, and MFG Stevens. (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 60:5196–5203.
  • AK Ghose, and GM Crippen. (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 27:21–35.
  • MR Grimmet. Imidazoles and their benzo derivativesComprehensive heterocyclic chemistryAR Katritzky, and CW Rees. Pergamon, Oxford, (1984) Vol. 5 457.
  • E-H Chew, CS Matthews, J Zhang, AJ McCarroll, T Hagen, MFG Stevens, AD Westwell, and TD Bradshaw. (2006). Antitumor quinols: Role of glutathione in modulating quinol-induced apoptosis and identification of putative cellular protein targets. Biochem Biophys Res Comm 346:242–251.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.