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Volumn 46, Issue 21, 2003, Pages 4609-4624

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)

(31)  Remiszewski, Stacy W a,b   Sambucetti, Lidia C a,c   Bair, Kenneth W a,d   Bontempo, John a   Cesarz, David a   Chandramouli, Nagarajan a   Chen, Ru a   Cheung, Min a   Cornell Kennon, Susan a   Dean, Karl a   Diamantidis, George a   France, Dennis a   Green, Michael A a   Howell, Kobporn Lulu a   Kashi, Rina a   Kwon, Paul a   Lassota, Peter a   Martin, Mary S a   Mou, Yin a   Perez, Lawrence B a   more..


Author keywords

[No Author keywords available]

Indexed keywords

4 [N (2 HYDROXYETHYL) N [2 (3 INDOLYL)ETHYL]AMINOMETHYL]CINNAMOHYDROXAMIC ACID; AMIDE; FLUOROURACIL; HISTONE DEACETYLASE INHIBITOR; MITOMYCIN C; N HYDROXY 3 [4 [[(2 HYDROXYETHYL)[2 (1H INDOL 3 YL)ETHYL]AMINO]METHYL]PHENYL] 2 PROPENAMIDE; N HYDROXY 3 PHENYL 2 PROPENAMIDE; UNCLASSIFIED DRUG;

EID: 10744229917     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030235w     Document Type: Article
Times cited : (129)

References (35)
  • 1
    • 0034387004 scopus 로고    scopus 로고
    • 25 Years after the nucleosome model: Chromatin modifications
    • Wu, J.; Grunstein, M. 25 years after the nucleosome model: chromatin modifications. Trends Biochem. Sci. 2000, 25, 619-623.
    • (2000) Trends Biochem. Sci. , vol.25 , pp. 619-623
    • Wu, J.1    Grunstein, M.2
  • 2
    • 0036211013 scopus 로고    scopus 로고
    • Histone acetylation: A switch between repressive and permissive chromatin. Second in review series on chromatin dynamics
    • Eberharter, A.; Becker, P. B. Histone acetylation: a switch between repressive and permissive chromatin. Second in review series on chromatin dynamics. EMBO Rep. 2002, 3, 224-229.
    • (2002) EMBO Rep. , vol.3 , pp. 224-229
    • Eberharter, A.1    Becker, P.B.2
  • 4
    • 0036008097 scopus 로고    scopus 로고
    • Deacetylase enzymes biological functions and the use of small-molecule inhibitors
    • Grozinger, C. M.; Schreiber, S. L. Deacetylase enzymes biological functions and the use of small-molecule inhibitors. Chem. Biol. 2002, 9, 3-16.
    • (2002) Chem. Biol. , vol.9 , pp. 3-16
    • Grozinger, C.M.1    Schreiber, S.L.2
  • 6
    • 0033000990 scopus 로고    scopus 로고
    • Histone acetylases and deacetylases in cell proliferation
    • Kouzarides, T. Histone acetylases and deacetylases in cell proliferation. Curr. Opin. Genet. Dev. 1999, 9, 40-48.
    • (1999) Curr. Opin. Genet. Dev. , vol.9 , pp. 40-48
    • Kouzarides, T.1
  • 8
    • 0036651788 scopus 로고    scopus 로고
    • Recent advances in the discovery of small molecule histone deacetylase inhibitors
    • Remiszewski, S. W. Recent advances in the discovery of small molecule histone deacetylase inhibitors. Curr. Opin. Drug Discovery Dev 2002, 5, 487-499.
    • (2002) Curr. Opin. Drug Discovery Dev. , vol.5 , pp. 487-499
    • Remiszewski, S.W.1
  • 9
    • 0034837064 scopus 로고    scopus 로고
    • Inhibitors of histone deacetylase as new anticancer agents
    • Jung, M. Inhibitors of histone deacetylase as new anticancer agents. Curr. Med. Chem. 2001, 8, 1505-1511.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1505-1511
    • Jung, M.1
  • 10
    • 0036527775 scopus 로고    scopus 로고
    • Histone-deacetylase inhibitors: Novel drugs for the treatment of cancer
    • Johnstone, R. W. Histone-deacetylase inhibitors: novel drugs for the treatment of cancer. Nat. Rev. Drug Discovery 2002, 1, 287-299.
    • (2002) Nat. Rev. Drug Discovery , vol.1 , pp. 287-299
    • Johnstone, R.W.1
  • 13
    • 0024996768 scopus 로고
    • Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A
    • Yoshida, M.; Kijima, M.; Akita, M.; Beppu, T. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A. J. Biol. Chem. 1990, 265, 17174-17179.
    • (1990) J. Biol. Chem. , vol.265 , pp. 17174-17179
    • Yoshida, M.1    Kijima, M.2    Akita, M.3    Beppu, T.4
  • 14
    • 0030744926 scopus 로고    scopus 로고
    • Analogues of trichostatin A and trapoxin B as histone deacetylase inhibitors
    • Jung, M.; Hoffmann, K.; Brosch, G.; Loidl, P. Analogues of trichostatin A and trapoxin B as histone deacetylase inhibitors. Bioorg. Med. Chem. Lett. 1997, 7, 1655-1658.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 1655-1658
    • Jung, M.1    Hoffmann, K.2    Brosch, G.3    Loidl, P.4
  • 16
    • 0027378351 scopus 로고
    • Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase
    • Kijima, M.; Yoshida, M.; Sugita, K.; Horinouchi, S.; Beppu, T. Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase. J. Biol. Chem. 1993, 268, 22429-22435.
    • (1993) J. Biol. Chem. , vol.268 , pp. 22429-22435
    • Kijima, M.1    Yoshida, M.2    Sugita, K.3    Horinouchi, S.4    Beppu, T.5
  • 17
    • 0033523895 scopus 로고    scopus 로고
    • Amide analogues of trichostatin a as inhibitors of histone deacetylase and inducers of terminal cell differentiation
    • Jung, M.; Brosch, G.; Koelle, D.; Scherf, H.; Gerhaeuser, C.; Loidl, P. Amide analogues of trichostatin a as inhibitors of histone deacetylase and inducers of terminal cell differentiation. J. Med. Chem. 1999, 42, 4669-4679.
    • (1999) J. Med. Chem. , vol.42 , pp. 4669-4679
    • Jung, M.1    Brosch, G.2    Koelle, D.3    Scherf, H.4    Gerhaeuser, C.5    Loidl, P.6
  • 18
    • 0035961036 scopus 로고    scopus 로고
    • Synthesis of 7200 small molecules based on a substructural analysis of the histone deacetylase inhibitors trichostatin and trapoxin
    • Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Synthesis of 7200 small molecules based on a substructural analysis of the histone deacetylase inhibitors trichostatin and trapoxin. Org. Lett. 2001, 3, 4239-4242.
    • (2001) Org. Lett. , vol.3 , pp. 4239-4242
    • Sternson, S.M.1    Wong, J.C.2    Grozinger, C.M.3    Schreiber, S.L.4
  • 19
    • 0009672045 scopus 로고
    • Topochemical photopolymerization of 4-[2-(unsubstituted and methyl-substituted pyrazinyl)ethenyl]cinnamates and -thiocinnamates in the crystalline state
    • Saigo, K.; Sukegawa, M.; Maekawa, Y.; Hasegqwa, M. Topochemical photopolymerization of 4-[2-(unsubstituted and methyl-substituted pyrazinyl)ethenyl]cinnamates and -thiocinnamates in the crystalline state. Bull. Chem. Soc. Jpn. 1995, 68, 2355-2362.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 2355-2362
    • Saigo, K.1    Sukegawa, M.2    Maekawa, Y.3    Hasegqwa, M.4
  • 20
    • 0033371222 scopus 로고    scopus 로고
    • Preparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 2. Condensed heterocyclic derivatives
    • Ono, S.; Yoshida, T.; Maeda, K.; Kosaka, K.; Inoue, Y.; Imada, T.; Fukaya, C., Nakamura, N. Preparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 2. Condensed heterocyclic derivatives. Chem. Pharm. Bull. 1999, 47, 1694-1712.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1694-1712
    • Ono, S.1    Yoshida, T.2    Maeda, K.3    Kosaka, K.4    Inoue, Y.5    Imada, T.6    Fukaya, C.7    Nakamura, N.8
  • 21
    • 0001173496 scopus 로고
    • Sodium acyloxyborohydrides as new reducing agents. 1. Reduction of carboxamides to the corresponding amines
    • Umino, N.; Iwakuma, T.; Itoh, N. Sodium acyloxyborohydrides as new reducing agents. 1. Reduction of carboxamides to the corresponding amines. Tetrahedron Lett. 1976, 763-766.
    • (1976) Tetrahedron Lett. , pp. 763-766
    • Umino, N.1    Iwakuma, T.2    Itoh, N.3
  • 22
    • 0033520944 scopus 로고    scopus 로고
    • Histone deacetylase inhibition selectively alters the activity and expression of cell cycle proteins leading to specific chromatin acetylation and antiproliferative effects
    • Sambucetti, L. C.; Fischer, D. D.; Zabludoff, S.; Kwon, P. O.; Chamberlin, H.; Trogani, N.; Xu, H.; Cohen, D. Histone deacetylase inhibition selectively alters the activity and expression of cell cycle proteins leading to specific chromatin acetylation and antiproliferative effects. J. Biol. Chem. 1999, 274, 34940-34947.
    • (1999) J. Biol. Chem. , vol.274 , pp. 34940-34947
    • Sambucetti, L.C.1    Fischer, D.D.2    Zabludoff, S.3    Kwon, P.O.4    Chamberlin, H.5    Trogani, N.6    Xu, H.7    Cohen, D.8
  • 27
    • 0009561422 scopus 로고
    • Studies in biomimetic alkaloid syntheses. 4. An alternative route to secodine intermediates providing syntheses of minovine, vincadifformine, ervinceine, and N(a)-methylervinceine
    • Kuehne, M. E.; Huebner, J. A.; Matsko, T. H. Studies in biomimetic alkaloid syntheses. 4. An alternative route to secodine intermediates providing syntheses of minovine, vincadifformine, ervinceine, and N(a)-methylervinceine. J. Org. Chem. 1979, 44, 2477-2480.
    • (1979) J. Org. Chem. , vol.44 , pp. 2477-2480
    • Kuehne, M.E.1    Huebner, J.A.2    Matsko, T.H.3
  • 29
    • 0028031424 scopus 로고
    • New synthesis of 1-substituted 3-(2-aminoethyl)indoles
    • Guenjoer, T.; Malabre, P.; Teulon, J. M. New synthesis of 1-substituted 3-(2-aminoethyl)indoles. Synth. Commun. 1994, 24, 2247-2256.
    • (1994) Synth. Commun. , vol.24 , pp. 2247-2256
    • Guenjoer, T.1    Malabre, P.2    Teulon, J.M.3
  • 31
    • 0001593308 scopus 로고
    • 6-Isotryptaminopurine
    • Schindler, W. 6-Isotryptaminopurine. Helv. Chim. Acta 1957, 40, 2156-2159.
    • (1957) Helv. Chim. Acta , vol.40 , pp. 2156-2159
    • Schindler, W.1
  • 32
    • 0014354866 scopus 로고
    • Central nervous system depressants. IV. 2-Aminoalkyl-1,2-dihyro-3H-imidazo[1,5-a]indol-3-ones
    • Wright, W. B., Jr.; Brabander, H. J. Central nervous system depressants. IV. 2-Aminoalkyl-1,2-dihyro-3H-imidazo[1,5-a]indol-3-ones. J. Med. Chem. 1968, 11, 1164-1167.
    • (1968) J. Med. Chem. , vol.11 , pp. 1164-1167
    • Wright W.B., Jr.1    Brabander, H.J.2
  • 33
    • 0035139001 scopus 로고    scopus 로고
    • 2 tetradentate ligands suitable for nuclear medicine applications
    • 2 tetradentate ligands suitable for nuclear medicine applications. Synlett 2001, 126-128.
    • (2001) Synlett , pp. 126-128
    • Fourteau, L.1    Benoist, E.2    Dartiguenave, M.3
  • 34
    • 0034031845 scopus 로고    scopus 로고
    • Synthesis of annelated imidazoles and benzimidazoles
    • McClure, J. R.; Custer, J. H.; Schwarz, H. D.; Lill, D. A. Synthesis of annelated imidazoles and benzimidazoles. Synlett 2000, 710-712.
    • (2000) Synlett , pp. 710-712
    • McClure, J.R.1    Custer, J.H.2    Schwarz, H.D.3    Lill, D.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.