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A New Class of Highly Potent Farnesyl Diphosphate-Competitive Inhibitors of Farnesyltransferase

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Drug Discovery Research Laboratories and Biomedical Research Laboratories, Tsukuba Research Institute, Banyu Pharmaceutical Co. Ltd., Okubo 3 Tsukuba 300-26, Japan
Cite this: J. Med. Chem. 1998, 41, 2, 143–147
Publication Date (Web):January 15, 1998
https://doi.org/10.1021/jm970540f
Copyright © 1998 American Chemical Society

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    Cited By

    This article is cited by 23 publications.

    1. Mitchell J. Polley,, David A. Winkler, and, Frank R. Burden. Broad-Based Quantitative Structure−Activity Relationship Modeling of Potency and Selectivity of Farnesyltransferase Inhibitors Using a Bayesian Regularized Neural Network. Journal of Medicinal Chemistry 2004, 47 (25) , 6230-6238. https://doi.org/10.1021/jm049621j
    2. Tammy C. Turek,, Igor Gaon, and, Mark D. Distefano, , Corey L. Strickland. Synthesis of Farnesyl Diphosphate Analogues Containing Ether-Linked Photoactive Benzophenones and Their Application in Studies of Protein Prenyltransferases. The Journal of Organic Chemistry 2001, 66 (10) , 3253-3264. https://doi.org/10.1021/jo991130x
    3. Todd J. Zahn,, Markus Eilers,, Zhengmao Guo,, Mohamad B. Ksebati,, Matthew Simon,, Jeffrey D. Scholten,, Steven O. Smith, and, Richard A. Gibbs. Evaluation of Isoprenoid Conformation in Solution and in the Active Site of Protein-Farnesyl Transferase Using Carbon-13 Labeling in Conjunction with Solution- and Solid-State NMR. Journal of the American Chemical Society 2000, 122 (30) , 7153-7164. https://doi.org/10.1021/ja000860f
    4. Elie Giraud,, Claude Luttmann,, François Lavelle,, Jean-François Riou,, Patrick Mailliet, and, Abdelazize Laoui. Multivariate Data Analysis Using D-Optimal Designs, Partial Least Squares, and Response Surface Modeling:  A Directional Approach for the Analysis of Farnesyltransferase Inhibitors. Journal of Medicinal Chemistry 2000, 43 (9) , 1807-1816. https://doi.org/10.1021/jm991166h
    5. Kareem A. H. Chehade,, Douglas A. Andres,, Hiromi Morimoto, and, H. Peter Spielmann. Design and Synthesis of a Transferable Farnesyl Pyrophosphate Analogue to Ras by Protein Farnesyltransferase. The Journal of Organic Chemistry 2000, 65 (10) , 3027-3033. https://doi.org/10.1021/jo991735t
    6. Melanie J. Blanden, Sudhat Ashok, James L. Hougland. Mechanisms of CaaX Protein Processing: Protein Prenylation by FTase and GGTase-I. 2020, 497-527. https://doi.org/10.1016/B978-0-12-409547-2.14837-1
    7. James J. Fiordalisi, Adrienne D. Cox. Farnesyltransferase Inhibitors. 2010, 1819-1826. https://doi.org/10.1016/B978-0-12-374145-5.00222-9
    8. Kimberly T. Lane, Lorena S. Beese. Thematic review series: Lipid Posttranslational Modifications. Structural biology of protein farnesyltransferase and geranylgeranyltransferase type I. Journal of Lipid Research 2006, 47 (4) , 681-699. https://doi.org/10.1194/jlr.R600002-JLR200
    9. D. W. End, L. Mevellec, P. Angibaud. Farnesyl Protein Transferase Inhibitors: Medicinal Chemistry, Molecular Mechanisms, and Progress in the Clinic. 2006, 133-168. https://doi.org/10.1007/7355_2006_003
    10. Y. L. Janin. Peptides with anticancer use or potential. Amino Acids 2003, 25 (1) , 1-40. https://doi.org/10.1007/s00726-002-0349-x
    11. James J. Fiordalisi, Adrienne D. Cox. Farnesyltransferase Inhibitors. 2003, 737-744. https://doi.org/10.1016/B978-012124546-7/50605-7
    12. Kimberly L. Terry, Stephen B. Long, Lorena S. Beese. 2 Structure of protein farnesyltransferase. 2001, 19-46. https://doi.org/10.1016/S1874-6047(01)80015-9
    13. Jackson B. Gibbs. 4 Farnesyltransferase inhibitors. 2001, 81-103. https://doi.org/10.1016/S1874-6047(01)80017-2
    14. Nicholas J.S Harmat, Silvia Mangani, Enzo Perrotta, Danilo Giannotti, Rossano Nannicini, Maria Altamura. Enantioselective syntheses of orthogonally protected tricarballylic acid esters. Tetrahedron Letters 2000, 41 (8) , 1261-1264. https://doi.org/10.1016/S0040-4039(99)02264-9
    15. Russell B. Lingham, Sheo B. Singh. Farnesyl-Protein Transferase: A New Paradigm for Cancer Chemotherapy, Advances in Discovery and Development of Natural Product Inhibitors. 2000, 403-472. https://doi.org/10.1016/S1572-5995(00)80050-2
    16. NANCY E. KOHL. Farnesyltransferase Inhibitors: Preclinical Development. Annals of the New York Academy of Sciences 1999, 886 (1) , 91-102. https://doi.org/10.1111/j.1749-6632.1999.tb09404.x
    17. Martin Schlitzer, Isabel Sattler. Aromatic carboxylic acids as farnesyl surrogates in farnesylpyrophosphate-based farnesyltransferase inhibitors. Bioorganic & Medicinal Chemistry 1999, 7 (11) , 2391-2395. https://doi.org/10.1016/S0968-0896(99)00191-1
    18. Theresa M Williams. Inhibitors of protein prenylation 1999. Expert Opinion on Therapeutic Patents 1999, 9 (9) , 1263-1280. https://doi.org/10.1517/13543776.9.9.1263
    19. Wang Shen, Stephen Fakhoury, Greg Donner, Kenneth Henry, Jang Lee, Haichao Zhang, Jerry Cohen, Robert Warner, Badr Saeed, Sajeev Cherian, Stephen Tahir, Peter Kovar, Joy Bauch, Shi-Chung Ng, Kennan Marsh, Hing Sham, Saul Rosenberg. Potent inhibitors of protein farnesyltransferase: Heteroarenes as cysteine replacements. Bioorganic & Medicinal Chemistry Letters 1999, 9 (5) , 703-708. https://doi.org/10.1016/S0960-894X(99)00080-3
    20. Amelia Moreno Barber, Ian R Hardcastle, Martin G Rowlands, Bernard P Nutley, Jonathan H Marriott, Michael Jarman. Solid-phase synthesis of novel inhibitors of Farnesyl Transferase. Bioorganic & Medicinal Chemistry Letters 1999, 9 (4) , 623-626. https://doi.org/10.1016/S0960-894X(99)00043-8
    21. Jeffrey T Eummer, Barbara S Gibbs, Todd J Zahn, Judith S Sebolt-Leopold, Richard A Gibbs. Novel limonene phosphonate and farnesyl diphosphate analogues: design, synthesis, and evaluation as potential protein-farnesyl transferase inhibitors. Bioorganic & Medicinal Chemistry 1999, 7 (2) , 241-250. https://doi.org/10.1016/S0968-0896(98)00202-8
    22. Mari Yonemoto, Toshihiko Satoh, Hiroharu Arakawa, Ikuko Suzuki-Takahashi, Yoshiaki Monden, Tsutomu Kodera, Kenji Tanaka, Tetsuya Aoyama, Yoshikazu Iwasawa, Toshio Kamei, Susumu Nishimura, Koji Tomimoto. J-104,871, a Novel Farnesyltransferase Inhibitor, Blocks Ras Farnesylation In Vivo in a Farnesyl Pyrophosphate-Competitive Manner. Molecular Pharmacology 1998, 54 (1) , 1-7. https://doi.org/10.1124/mol.54.1.1
    23. Martin Schlitzer. Hemmstoffe der Farnesyltransferase: Ein neuer Ansatz zur Entwicklung potentieller Krebstherapeutika. Pharmazie in unserer Zeit 1998, 27 (6) , 278-288. https://doi.org/10.1002/pauz.19980270608

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