Synthesis of novel hydroxamate and non-hydroxamate histone deacetylase inhibitors

Current Opinion in Drug Discovery and Development

Volumn 7, Issue 6, 2004, Pages 848-868

  Curtin, Michael L ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Cancer; FK 228; HDAC inhibitor; Histone deacetylase; MS 275; NVP LAQ 824; Suberanilohydroxamic acid

Indexed keywords

3 PHENYLSULFAMOYLCINNAMOHYDROXAMIC ACID; 4 [N (2 HYDROXYETHYL) N [2 (3 INDOLYL)ETHYL]AMINOMETHYL]CINNAMOHYDROXAMIC ACID; ARYLBUTYRIC ACID DERIVATIVE; BENZAMIDE DERIVATIVE; BUTYRIC ACID DERIVATIVE; CINNAMIC ACID DERIVATIVE; DEPSIPEPTIDE; FR 901228; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID DERIVATIVE; N (2 AMINOPHENYL) 4 (3 PYRIDINYLMETHOXYCARBONYLAMINOMETHYL)BENZAMIDE; OXAZOLE DERIVATIVE; SUBERANILOHYDROXAMIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CANCER; CLINICAL TRIAL; DRUG STRUCTURE; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; HUMAN; LEUKEMIA; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHARMACOPHORE; PHASE 1 CLINICAL TRIAL; PHASE 2 CLINICAL TRIAL; REVIEW; SOLID TUMOR; VILSMEIER HAACK REACTION;

ACETYLATION; ENZYME INHIBITORS; HISTONE DEACETYLASES; HYDROXAMIC ACIDS; PEPTIDES;

EID: 10444287560     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (41)

1. Cheung WL, Briggs SD, Allis CD: Acetylation and chromosomal functions. Curr Opin Cell Biol (2000) 12(3):326-333.
2. Vigushin DM, Coombes RC: Targeted histone deacetylase inhibition for cancer therapy. Curr Cancer Drug Targets (2004) 4(2):205-218.
3. De Ruijter AJ, Van Gennip AH, Caron HN, Kemp S, Van Kuilenburg AB: Histone deacetylases (HDACs): Characterization of the classical HDAC family. Biochem J (2003) 370(Pt 3):737-749. Thorough summary of class I and II HDACs.
4. Lindemann RK, Gabrielli B, Johnstone RW: Histone-deacetylase inhibitors for the treatment of cancer. Cell Cycle (2004) 3(6):779-788. Includes discussion of HDAC-mediated transcription-independent events.
5. Finnin MS, Donigian JR, Cohen A, Richon VM, Rifkind RA, Marks PA, Breslow R, Pavletich NP: Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors. Nature (1999) 401 (6749): 188-193. First structural study of bound HDAC inhibitors.
6. Kristeleit R, Stimson L, Workman P, Aherne W: Histone modification enzymes: Novel targets for cancer drugs. Expert Opin Emerging Drugs (2004) 9(1):135-154. Excellent summary of the latest HDAC biology and clinical results.
7. Richon VM, Webb Y, Merger R, Sheppard T, Jursic B, Ngo L, Civoli F, Breslow R, Rifkind RA, Marks PA: Second generation hybrid polar compounds are potent inducers of transformed cell differentiation. Proc Natl Acad Sci USA (1996) 93(12):5705-5709.
8. Johnstone RW: Suberanilohydroxamic Acid. Aton Pharma. IDrugs (2004) 7(7):674-682.
9. Dai Y, Guo Y, Guo J, Pease LJ, Li J, Marcotte PA, Glaser KB, Tapang P, Albert DH, Richardson PL, Davidsen SK et al: Indole amide hydroxamic acids as potent inhibitors of histone deacetylases. Bioorg Med Chem Lett (2003) 13(11):1897-1901.
10. Dai Y, Guo Y, Curtin ML, Li J, Pease LJ, Guo J, Marcotte PA, Glaser KB, Davidsen SK, Michaelides MR: A novel series of histone deacetylase inhibitors incorporating hetero aromatic ring systems as connection units. Bioorg Med Chem Lett (2003) 13(21):3817-3820.
11. Van Ommeslaeghe K, Elaut G, Brecx V, Papeleu P, Iterbeke K, Geerlings P, Tourwe D, Rogiers V: Amide analogues of TSA: Synthesis, binding mode analysis and HDAC inhibition. Bioorg Med Chem Lett (2003) 13(11):1861-1864.
12. Remiszewski SW, Sambucetti LC, Bair KW, Bontempo J, Cesarz D, Chandramouli N, Chen R, Cheung M, Cornell-Kennon S, Dean K, Diamantidis G et al: N-Hydroxy-3-phenyl-2-propenamides as novel inhibitors of human histone deacetylase with in vivo antitumor activity: Discovery of (2E)-N-hydroxy-3-[4- [[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2-propenamide (NVP-LAQ824). J Med Chem (2003) 46(21):4609-4624.
13. Plumb JA, Finn PW, Williams RJ, Bandara MJ, Romero MR, Watkins CJ, La Thangue NB, Brown R: Pharmacodynamic response and inhibition of growth of human tumor xenografts by the novel histone deacetylase inhibitor PXD101. Mol Cancer Ther (2003) 2(8):721-728.
14. Bouchain G, Leit S, Frechette S, Khalil EA, Lavoie R, Moradei O, Woo SH, Fournel M, Yan PT, Kalita A, Trachy-Bourget MC et al: Development of potential antitumor agents. Synthesis and biological evaluation of a new set of sulfonamide derivatives as histone deacetylase inhibitors. J Med Chem (2003) 46(5):820-830.
15. 2+-Chelating motif-tethered short-chain fatty acids as a novel class of histone deacetylase inhibitors. J Med Chem (2004) 47(2):467-474.
16. Kim DK, Lee JY, Kim JS, Ryu JS, Choi JY, Lee JW, Im GJ, Kim, TK, Seo JW, Park HJ, Yoo J et at. Synthesis and biological evaluation of 3-(4-substituted-phenyl)-W-hydroxy-2-propenamides, a new class of histone deacetylase inhibitors. J Med Chem (2003) 46(26):5745-5751.
17. Ragno R, Mai A, Massa S, Cerbara I, Valente S, Bottoni P, Scatena R, Jesacher F, Loidl P, Brosch G: 3-(4-Aroyl-1-methyl-1H-pyrrol-2-yl)-N-hydroxy-2- propenamides as a new class of synthetic histone deacetylase inhibitors. 3. Discovery of novel lead compounds through structure-based drug design and docking studies. J Med Chem (2004) 47(6):1351-1359.
18. Marson CM, Serradji N, Rioja AS, Gastaud SP, Alao JP, Coombes RC, Vigushi DM: Stereodefined and polyunsaturated inhibitors of histone deacetylase based on (2E,4E)-5-arylpenta-2,4-dienoic acid hydroxyamides. Bioorg Med Chem Lett (2004) 14(10):2477-2481.
19. Maeda T, Nagaoka MT, Kuwajima H, Seno C, Maruyama S, Kurotaki M, Uesato S: Potent histone deacetylase inhibitors: N-hydroxybenzamides with antitumor activities. Bioorg Med Chem (2004)12(16):4351-4360.
20. Bapna A, Vickerstaffe E, Warrington BH, Ladlow M, Fan TP, Ley SV: Polymer-assisted, multi-step solution phase synthesis and biological screening of histone deacetylase inhibitors. Org Biomol Chem (2004) 2(4):611-620.
21. Glenn MP, Kahnberg P, Boyle GM, Hansford KA, Hans D, Martyn AC, Parsons PG, Fairlie DP: Antiproliferative and phenotype-transforming antitumor agents derived from cysteine. J Med Chem (2004) 47(12):2984-2994.
22. Somoza JR, Skene RJ, Katz BA, Mol C, Ho JD, Jennings AJ, Luong C, Arvai A, Buggy JJ, Chi E, Tang J et. al. Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases. Structure (2004) 12(7):1325-1334. First X-ray crystal structure of a human HDAC.
23. Suzuki T, Ando T, Tsuchiya K, Fukazawa N, Saito A, Mariko Y, Yamashita T, Nakanishi O: Synthesis and histone deacetylase inhibitory activity of new benzamide derivatives. J Med Chem (1999) 42(15):3001-3003.
24. Vaisburg A, Bernstein N, Frechette S, Allan M, Abou-Khalil E, Leit S, Moradei O, Bouchain G, Wang J, Woo SH, Fournel M et al: (2-Aminophenyl)-amides of ω-substituted alkanoic acids as new histone deacetylase inhibitors. Bioorg Med Chem Lett (2004) 14(1):283-287.
25. Suzuki T, Kouketsu A, Matsuura A, Kohara A, Ninomiya S, Kohda K, Miyata N: Thiol-based SAHA analogues as potent histone deacetylase inhibitors. Bioorg Med Chem Lett (2004) 14(12):3313-3317.
26. Suzuki T, Nagano Y, Matsuura A, Kohara A, Ninomiya S, Kohda K, Miyata N: Novel histone deacetylase inhibitors: Design, synthesis, enzyme inhibition, and binding mode study of SAHA-based non-hydroxamates. Bioorg Med Chem Lett (2003) 13(24):4321-4326.
27. Wu TY, Hassig C, Wu Y, Ding S, Schultz PG: Design, synthesis, and activity of HDAC inhibitors with a N-formyl hydroxylamine head group. Bioorg Med Chem Lett (2004) 14(2):449-453.
28. Kapustin GV, Fejèr G, Gronlund JL, McCafferty DG, Seto E, Etzkorn FA: Phosphorous-based SAHA analogues as histone deacetylase inhibitors. Org Lett (2003) 5(17):3053-3056.
29. Frey RR, Wada CK, Garland RB, Curtin ML, Michaelides MR, Li J, Pease LJ, Glaser KB, Marcotte PA, Bouska JJ, Murphy SS et at. Trifluoromethyl ketones as inhibitors of histone deacetylase. Bioorg Med Chem Lett (2002) 12(23):3443-3447.
30. Vasudevan A, Ji Z, Frey RR, Wada CK, Steinman D, Heyman RH, Guo Y, Curtin ML, Guo J, Li J, Pease L et al. Heterocyclic ketones as inhibitors of histone deacetylase. Bioorg Med Chem Lett (2003) 13(22):3909-3913.
31. Wada CK, Frey RR, Ji Z, Curtin ML, Garland RB, Holms JH, Li J, Pease LJ, Guo J, Glaser KB, Marcotte PA et al. α-Keto amides as inhibitors of histone deacetylase. Bioorg Med Chem Lett (2003) 13(19):3331-3335.
32. Furumai R, Matsuyama A, Kobashi N. Lee KH, Nishiyama M, Nakajima H, Tanaka A, Komatsu Y, Nishino N, Yoshida M, Horinouchi S: FK228 (Depsipeptide) as a natural prodrug that inhibits class I histone deacetylases. Cancer Res (2002) 62(17):4916-4921.
33. Li KW, Wu J, Xing W, Simon JA: Total synthesis of the antitumor depsipeptide FR-901,228. J Am Chem Soc (1996) 118:7237-7238.
34. Furumai R, Komatsu Y, Nishino N, Khochbin S, Yoshida M, Horinouchi S: Potent histone deacetylase Inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics including trapoxin. Proc Natl Acad Sci USA (2001) 98(1):87-92.
35. Nishino N, Arai T, Ueno Y, Ohba M: Tandem enzymatic resolution yielding L-α-aminoalkanedioic acid ω-esters. Chem Pharm Bull (Tokyo) (1996) 44(1):212-214.
36. Nishino N, Jose B, Okamura S, Ebisusaki S, Kato T, Sumida Y, Yoshida M: Cyclic tetrapetides bearing a sulfhydryl group potently inhibit histone deacetylases. Org Lett (2003) 5(26):5079-5082.
37. Watanabe LA, Jose B, Kato T, Nishino N, Yoshida M: Synthesis of u-α-amino-ω-bromoalkanoic acid for side chain modification. Tetrahedron Lett (2004) 45(3):491-494.
38. Nishino N, Yoshikawa D, Watanabe LA, Kato T, Jose B, Komatsu Y, Sumida Y, Yoshida M: Synthesis and histone deacetylase inhibitory activity of cyclic tetrapeptides containing a retrohydroxamate as zinc ligand. Bioorg Med Chem Lett (2004) 14(10):2427-2431.
39. Curtin ML, Garland RB, Heyman HR, Frey RR, Michaelides MR, Li J, Pease LJ, Glaser KB, Marcotte PA, Davidsen SK: Succinimide hydroxamic acids as potent inhibitors of histone deacetylase (HDAC). Bioorg Med Chem Lett (2002) 12(20):2919-2923.
40. PROLIFIX LTD (Watkins CJ, Romero-Martin MR, Moore KG, Ritchie J, Finn PW, Kalvinsh I, Loza E, Dikovska K, Gailite V, Vorona M, Piskunova I et al): Carbamic acid compounds comprising a sulfonamide linkage as HDAC inhibitors. WO-00230879 (2002).
41. FUJISAWA PHARMACEUTICAL Co LTD (Ueda S, Watamoto Y, Tsuboi M, Kanda M, Higaki T, Matsuda M): A method of producing FR901228. WO-00220817 (2002).