Three-dimensional quantitative structure–farnesyltransferase inhibition analysis for some diaminobenzophenones

References

• Bell DR, Jorgensen P, Christophel EM, Palmer KL. Malaria risk estimation of the malaria burden. Nature 2005;437:E3–4.
   PubMed Web of Science ®Google Scholar
• Snow RW, Guerra CA, Noor AM, Myint HY, Hay SI. The global distribution of clinical episodes of plasmodium falciparum malaria. Nature 2005;434:214–17.
   PubMed Web of Science ®Google Scholar
• Rosenthal PJ. Antimalarial drug discovery: old and new approaches. J Exp Biol 2003;206:3735–44.
   PubMed Web of Science ®Google Scholar
• Schlitzer M. Malaria chemotherapeutics part 1: History of antimalarial drug development, currently used therapeutics, and drugs in clinical development. ChemMedChem 2007;2:944–86.
   PubMed Web of Science ®Google Scholar
• Baird JK. Effectiveness of antimalarial drugs. N Engl J Med 2005;352:1565–77.
   PubMed Web of Science ®Google Scholar
• Brady RL, Cameron A. Structure-based approaches to the development of novel anti-malarials. Curr Drug Target 2004;5:137–49.
   PubMed Web of Science ®Google Scholar
• Eastman RT, White J, Hucke O, Bauer K, Yokoyama K, Nallan L, Chakrabarti D, Verlinde CLMJ, Gelb MH, Rathod PK, Van Voorhis WC. Resistance to a protein farnesyltransferase inhibitor in Plasmodium falciparum. J Biol Chem 2005;280:13554–9.
   PubMed Web of Science ®Google Scholar
• Fidock DA, Rosenthal PJ, Croft SL, Brun R, Nwaka S. Antimalarial drug discovery: efficacy models for compound screening. Nat Rev Drug Discov 2004;3:509–20.
   PubMed Web of Science ®Google Scholar
• Wiesner J, Ortmann R, Jomaa H, Schlitzer M. New antimalarial drugs. Angew Chem Int Ed Engl 2003;42:5274–93.
   PubMed Web of Science ®Google Scholar
• Eastman RT, Buckner FS, Yokoyama K, Gelb MH, Van Voorhis WC. Thematic review series: lipid posttranslational modifications. Fighting parasitic disease by blocking protein farnesylation. J Lipid Res 2006;47:233–40.
   PubMed Web of Science ®Google Scholar
• Gelb MH, Van Voorhis WC, Buckner FS, Yokoyama K, Eastman R, Carpenter EP, Panethymitaki C, Brown KA, Smith DF. Protein farnesyl and n-myristoyl transferases: piggy-back medicinal chemistry targets for the development of antitrypanosomatid and antimalarial therapeutics. Mol Biochem Parasitol 2003;126:155–63.
   PubMed Web of Science ®Google Scholar
• Appels NMGM, Beijnen JH, Schellens JHM. Development of farnesyl transferase inhibitors: a review. Oncologist 2005;10:565–78.
   PubMed Web of Science ®Google Scholar
• Dinsmore CJ, Bell IM. Inhibitors of farnesyltransferase and geranylgeranyltransferase-I for antitumor therapy: substrate-based design, conformational constraint and biological activity. Curr Top Med Chem 2003;3:1075–93.
   PubMed Web of Science ®Google Scholar
• Pan J, Yeung S-CJ. Recent advances in understanding the antineoplastic mechanisms of farnesyltransferase inhibitors. Cancer Res 2005;65:9109–12.
   PubMed Web of Science ®Google Scholar
• Sebti SM, Hamilton AD. Farnesyltransferase and geranylgeranyl transferase I inhibitors and cancer therapy: lessons from mechanism and bench-to-bedside translational studies. Oncogene 2000;19:6584–93.
   PubMed Web of Science ®Google Scholar
• Carrico D, Ohkanda J, Kendrick H, Yokoyama K, Blaskovich MA, Bucher CJ, Buckner FS, Van Voorhis WC, Chakrabarti D, Croft SL, Gelb MH, Sebti SM, Hamilton AD. In vitro and in vivo antimalarial activity of peptidomimetic protein farnesyltransferase inhibitors with improved membrane permeability. Bioorg Med Chem 2004;12:6517–26.
   PubMed Web of Science ®Google Scholar
• Nallan L, Bauer KD, Bendale P, Rivas K, Yokoyama K, Horney CP, Pendyala PR, Floyd D, Lombardo LJ, Williams DK, Hamilton A, Sebti S, Windsor WT, Weber PC, Buckner FS, Chakrabarti D, Gelb MH, VanVoorhis WC. Protein farnesyltransferase inhibitors exhibit potent antimalarial activity. J Med Chem 2005;48:3704–13.
   PubMed Web of Science ®Google Scholar
• Wiesner J, Kettler K, Sakowski J, Ortmann R, Katzin AM, Kimura EA, Silber K, Klebe G, Jomaa H, Schlitzer M. Farnesyltransferase inhibitors inhibit the growth of malaria parasites in vitro and in vivo. Angew Chem Int Ed Engl 2004;43:251–4.
   PubMed Web of Science ®Google Scholar
• Kettler K, Sakowski J, Silber K, Sattler I, Klebe G, Schlitzer M. Non-thiol farnesyltransferase inhibitors: N-(4-acylamino-3-benzoylphenyl)-3-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides. Bioorg Med Chem 2003;11:1521–30.
   PubMed Web of Science ®Google Scholar
• Kettler K, Wiesner J, Fucik K, Sakowski J, Ortmann R, Dahse H-M, Jomaa H, Schlitzer M. 2-(Aminoacylamino)benzophenones: farnesyltransferase inhibition and antimalarial activity. Pharmazie 2005;60:677–82.
   PubMed Web of Science ®Google Scholar
• Kettler K, Wiesner J, Silber K, Haebel P, Ortmann R, Sattler I, Dahse H-M, Jomaa H, Klebe G, Schlitzer M. Non-thiol farnesyltransferase inhibitors: N-(4-aminoacylamino-3-benzoylphenyl)-3-[5-(4-nitrophenyl)-2 furyl]acrylic acid amides and their antimalarial activity. Eur J Med Chem 2005;40:93–101.
   PubMed Web of Science ®Google Scholar
• Mitsch A, Bohm M, Wißner P, Sattler I, Schlitzer M. Non-thiol farnesyltransferase inhibitors: utilization of an aryl binding site by 5-arylacryloylaminobenzophenones. Bioorg Med Chem 2002;10:2657–62.
   PubMed Web of Science ®Google Scholar
• Mitsch A, Wißner P, Silber K, Haebel P, Sattler I, Klebe G, Schlitzer M. Non-thiol farnesyltransferase inhibitors: N-(4-tolylacetylamino-3-benzoylphenyl)-3-arylfurylacrylic acid amides. Bioorg Med Chem 2004;12:4585–600.
   PubMed Web of Science ®Google Scholar
• Sakowski J, Sattler I, Schlitzer M. Non-thiol farnesyltransferase inhibitors: N-(4-acylamino-3-benzoylphenyl)-4-nitrocinnamic acid amides. Bioorg Med Chem 2002;10:233–9.
   PubMed Web of Science ®Google Scholar
• Cramer RD III, Patterson DE, Bunce JD. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 1988;110:5959–67.
   PubMed Web of Science ®Google Scholar
• Klebe G, Abraham U, Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 1994;37:4130–46.
   PubMed Web of Science ®Google Scholar
• Equbal T, Silakari O, Ravikumar M. Exploring three-dimensional quantitative structural activity relationship (3D-QSAR) analysis of SCH 66336 (Sarasar) analogues of farnesyltransferase inhibitors. Eur J Med Chem 2008;43:204–9.
   PubMed Web of Science ®Google Scholar
• Murumkar PR, Giridhar R, Yadav MR. 3D-quantitative structure-activity relationship studies on benzothiadiazepine hydroxamates as inhibitors of tumor necrosis factor-alpha converting enzyme. Chem Biol Drug Des 2008;71:363–73.
   PubMed Web of Science ®Google Scholar
• Puntambekar DS, Giridhar R, Yadav MR. Understanding the antitumor activity of novel tricyclicpiperazinyl derivatives as farnesyltransferase inhibitors using CoMFA and CoMSIA. Eur J Med Chem 2006;41:1279–92.
   PubMed Web of Science ®Google Scholar
• Puntambekar DS, Giridhar R, Yadav MR. Insights into the structural requirements of farnesyltransferase inhibitors as potential anti-tumor agents based on 3D-QSAR CoMFA and CoMSIA models. Eur J Med Chem 2008;43:142–54.
   PubMed Web of Science ®Google Scholar
• Sung ND, Cho YK, Kwon BM, Hyun KH, Kim CK. 3D QSAR studies on cinnamaldehyde analogues as farnesyl protein transferase inhibitors. Arch Pharm Res 2004;27:1001–8.
   PubMed Web of Science ®Google Scholar
• Xie A, Sivaprakasam P, Doerksen RJ. 3D-QSAR analysis of antimalarial farnesyltransferase inhibitors based on a 2,5-diaminobenzophenone scaffold. Bioorg Med Chem 2006;14:7311–23.
   PubMed Web of Science ®Google Scholar
• Sybyl 7.2. St. Louis, MO: Tripos, Inc., 2005.
   Google Scholar
• Grubbs F. Procedures for detecting outlying observations in samples. Technometrics 1969;11:1–21.
   Web of Science ®Google Scholar
• Fucik K, Kettler K, Wiesner J, Ortmann R, Unterreitmeier D, Krauss J, Bracher F, Jomaa H, Schlitzer M. 2-(Arylpropionylamino)- and 2-(arylacryloylamino)benzophenones: farnesyltransferase inhibition and antimalarial activity. Pharmazie 2004;59:744–52.
   PubMed Web of Science ®Google Scholar
• Wiesner J, Ortmann R, Mitsch A, Wißner P, Sattler I, Jomaa H, Schlitzer M. Inhibitors of farnesyltransferase: 5-arylacryloylaminobenzophenones show antimalarial activity. Pharmazie 2003;58:288–9.
   PubMed Web of Science ®Google Scholar
• Bohm M, Mitsch A, Wißner P, Sattler I, Schlitzer M. Exploration of novel aryl binding sites of farnesyltransferase using molecular modeling and benzophenone-based farnesyltransferase inhibitors. J Med Chem 2001;44:3117–24.
   PubMed Web of Science ®Google Scholar