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Volumn 80, Issue 1, 2012, Pages 106-113

Discovery of Novel Acyl Coenzyme A: Cholesterol Acyltransferase Inhibitors: Pharmacophore-Based Virtual Screening, Synthesis and Pharmacology

Author keywords

ACAT inhibitors; Cost analysis; Predictive pharmacophore; Validation; Virtual screening

Indexed keywords

CHOLESTEROL ACYLTRANSFERASE; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; ETHYL 3,5 DIBROMO 4 [[[2 (PHENYLCARBONYL)PHENYL]CARBONYL]OXY]BENZOATE; ETHYL 3,5 DICHLORO 4 [[[2 (PHENYLCARBONYL)PHENYL]CARBONYL]OXY]BENZOATE; LIGAND; UNCLASSIFIED DRUG;

EID: 84862149887     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01384.x     Document Type: Article
Times cited : (15)

References (37)
  • 3
    • 3042733723 scopus 로고    scopus 로고
    • Cholesterol absorption and hepatic acyl-coenzyme A:cholesterol acyltransferase activity play major roles in lipemic response to dietary cholesterol and fat in laboratory opossums
    • Kushwaha R.S., Vandeberg J.F., Rodriguez R., Vandeberg J.L. (2004) Cholesterol absorption and hepatic acyl-coenzyme A:cholesterol acyltransferase activity play major roles in lipemic response to dietary cholesterol and fat in laboratory opossums. Metabolism;53:817-822.
    • (2004) Metabolism , vol.53 , pp. 817-822
    • Kushwaha, R.S.1    Vandeberg, J.F.2    Rodriguez, R.3    Vandeberg, J.L.4
  • 4
    • 0035081589 scopus 로고    scopus 로고
    • Acyl coenzyme A: cholesterol acyltransferase types 1 and 2: structure and function in atherosclerosis
    • Rudel L.L., Lee R.G., Cockman T.L. (2001) Acyl coenzyme A: cholesterol acyltransferase types 1 and 2: structure and function in atherosclerosis. Curr Opin Lipidol;12:121-127.
    • (2001) Curr Opin Lipidol , vol.12 , pp. 121-127
    • Rudel, L.L.1    Lee, R.G.2    Cockman, T.L.3
  • 5
    • 0020452213 scopus 로고
    • Effect of dietary fat saturation, cholesterol and cholestyramine on acyl-CoA: cholesterol acyltransferase activity in rabbit intestinal microsomes
    • Field F.J., Salome R.G. (1982) Effect of dietary fat saturation, cholesterol and cholestyramine on acyl-CoA: cholesterol acyltransferase activity in rabbit intestinal microsomes. Biochim Biophys Acta;712:557-570.
    • (1982) Biochim Biophys Acta , vol.712 , pp. 557-570
    • Field, F.J.1    Salome, R.G.2
  • 6
    • 0021043541 scopus 로고
    • Role of acyl CoA:cholesterol acyltransferase in cholesterol absorption and its inhibition by 57-118 in the rabbit
    • Heider J.G., Pickens C.E., Kelly L.A. (1983) Role of acyl CoA:cholesterol acyltransferase in cholesterol absorption and its inhibition by 57-118 in the rabbit. J Lipid Res;24:1127-1134.
    • (1983) J Lipid Res , vol.24 , pp. 1127-1134
    • Heider, J.G.1    Pickens, C.E.2    Kelly, L.A.3
  • 7
    • 0019139290 scopus 로고
    • Secretion of very low density lipoproteins enriched in cholesteryl esters by cultured rat hepatocytes during simulation of intracellular cholesterol esterification
    • Drevon C.A., Engelhorn S.C., Steinberg D. (1980) Secretion of very low density lipoproteins enriched in cholesteryl esters by cultured rat hepatocytes during simulation of intracellular cholesterol esterification. J Lipid Res;21:1065-1071.
    • (1980) J Lipid Res , vol.21 , pp. 1065-1071
    • Drevon, C.A.1    Engelhorn, S.C.2    Steinberg, D.3
  • 8
    • 0024554685 scopus 로고
    • Cholesterol is required for secretion of very-low-density lipoprotein by rat liver
    • Khan B., Wilcox H.G., Heimberg M. (1989) Cholesterol is required for secretion of very-low-density lipoprotein by rat liver. Biochem J;258:807-816.
    • (1989) Biochem J , vol.258 , pp. 807-816
    • Khan, B.1    Wilcox, H.G.2    Heimberg, M.3
  • 9
    • 0025667289 scopus 로고
    • Regulation of apoB secretion from HepG2 cells: evidence for a critical role for cholesteryl ester synthesis in the response to a fatty acid challenge
    • Cianflone K.M., Yasruel Z., Rodriguez M.A., Sniderman A.D. (1990) Regulation of apoB secretion from HepG2 cells: evidence for a critical role for cholesteryl ester synthesis in the response to a fatty acid challenge. J Lipid Res;31:2045-2055.
    • (1990) J Lipid Res , vol.31 , pp. 2045-2055
    • Cianflone, K.M.1    Yasruel, Z.2    Rodriguez, M.A.3    Sniderman, A.D.4
  • 10
    • 77956031015 scopus 로고    scopus 로고
    • Generation, validation and utilizaiton of three-dimensional pharmacophore model for EP3 antagonists
    • Mishra R.K., Singh J. (2010) Generation, validation and utilizaiton of three-dimensional pharmacophore model for EP3 antagonists. J Chem Inf Model;50:1502-1509.
    • (2010) J Chem Inf Model , vol.50 , pp. 1502-1509
    • Mishra, R.K.1    Singh, J.2
  • 11
    • 72949120874 scopus 로고    scopus 로고
    • Pharmacophore modelling of qualitative prediction of antiestrogenic activity
    • Brogi S., Kladi M., Vagias C., Papazafiri P., Roussis V., Tafi A. (2009) Pharmacophore modelling of qualitative prediction of antiestrogenic activity. J Chem Inf Model;49:2489-2497.
    • (2009) J Chem Inf Model , vol.49 , pp. 2489-2497
    • Brogi, S.1    Kladi, M.2    Vagias, C.3    Papazafiri, P.4    Roussis, V.5    Tafi, A.6
  • 12
    • 0037468539 scopus 로고    scopus 로고
    • Non-peptide angiotensin II receptor antagonists: chemical feature based pharmacophore identification
    • Krovat E.M., Langer T. (2003) Non-peptide angiotensin II receptor antagonists: chemical feature based pharmacophore identification. J Med Chem;46:716-726.
    • (2003) J Med Chem , vol.46 , pp. 716-726
    • Krovat, E.M.1    Langer, T.2
  • 13
    • 2442709037 scopus 로고    scopus 로고
    • Chemical function based pharmacophore generation of Endothelin-A selective receptor antagonists
    • Funk O.F., Kettmann V., Drimal J., Langer T. (2004) Chemical function based pharmacophore generation of Endothelin-A selective receptor antagonists. J Med Chem;47:2750-2760.
    • (2004) J Med Chem , vol.47 , pp. 2750-2760
    • Funk, O.F.1    Kettmann, V.2    Drimal, J.3    Langer, T.4
  • 15
    • 84862150994 scopus 로고    scopus 로고
    • QSAR study of a series of acyl coenzyme A (CoA): cholesterol acyltransferase inhibitors using genetic function approximation
    • Online first, DOI:
    • Chhabria M.T., Mahajan B.M., Brahmkshatriya P.S. (2010) QSAR study of a series of acyl coenzyme A (CoA): cholesterol acyltransferase inhibitors using genetic function approximation. Med Chem Res. Online first, DOI:.
    • (2010) Med Chem Res
    • Chhabria, M.T.1    Mahajan, B.M.2    Brahmkshatriya, P.S.3
  • 16
    • 0029892115 scopus 로고    scopus 로고
    • Inhibitors of Acyl-CoA: cholesterol O-Acyltransferase. Structure-activity relationships of several series of compounds derived from N-chlorosulfonylisocyanate
    • Picard J.A., O'Brien P.M., Sliskovic D.R., Anderson M.K., Bousley R.F., Hemelehle K.L., Krause B.R., Stanfield R.L. (1996) Inhibitors of Acyl-CoA: cholesterol O-Acyltransferase. Structure-activity relationships of several series of compounds derived from N-chlorosulfonylisocyanate. J Med Chem;39:1243-1252.
    • (1996) J Med Chem , vol.39 , pp. 1243-1252
    • Picard, J.A.1    O'Brien, P.M.2    Sliskovic, D.R.3    Anderson, M.K.4    Bousley, R.F.5    Hemelehle, K.L.6    Krause, B.R.7    Stanfield, R.L.8
  • 17
    • 0029898322 scopus 로고    scopus 로고
    • Inhibitors of Acyl-CoA: cholesterol O-Acyltransferase. Synthesis and pharmacological activity of (±)-2-dodecyl-phenyl-N-(2,4,6,trimethoxy)-2H-tetrazole-5-acetamide and structurally related tetrazole amide derivatives
    • O' Brien P.M., Sliskocic D.R., Picard J.A., Lee H.T., Purchase C.F., Roth B.D., White A.D. et al. (1996) Inhibitors of Acyl-CoA: cholesterol O-Acyltransferase. Synthesis and pharmacological activity of (±)-2-dodecyl-phenyl-N-(2, 4, 6, trimethoxy)-2H-tetrazole-5-acetamide and structurally related tetrazole amide derivatives. J Med Chem;39:2354-2366.
    • (1996) J Med Chem , vol.39 , pp. 2354-2366
    • O' Brien, P.M.1    Sliskocic, D.R.2    Picard, J.A.3    Lee, H.T.4    Purchase, C.F.5    Roth, B.D.6    White, A.D.7
  • 19
    • 15644364732 scopus 로고    scopus 로고
    • α-Substituted malonester amides: tools to define the relationship between ACAT inhibitors and adrenal toxicity
    • Sliskovic D.R., Picard J.A., O'Brien P.M., Liao P., Roark W.H., Roth B.D., Anderson M.A. et al. (1998) α-Substituted malonester amides: tools to define the relationship between ACAT inhibitors and adrenal toxicity. J Med Chem;41:682-690.
    • (1998) J Med Chem , vol.41 , pp. 682-690
    • Sliskovic, D.R.1    Picard, J.A.2    O'Brien, P.M.3    Liao, P.4    Roark, W.H.5    Roth, B.D.6    Anderson, M.A.7
  • 21
    • 0034935946 scopus 로고    scopus 로고
    • Strucure-activity relationships of N-(3,5-dimethoxy-4-n-octyloxycinnamoyl)-N9-(3,4-dimethylphenyl)piperazine and analogues as inhibitors of Acyl CoA:cholesterol O-Acyltransferase
    • Ohishi K., Aiyama R., Hatano H., Yoshida Y., Wada Y., Yokai W., Sawada H., Watanabe T., Yokokura T. (2001) Strucure-activity relationships of N-(3, 5-dimethoxy-4-n-octyloxycinnamoyl)-N9-(3, 4-dimethylphenyl)piperazine and analogues as inhibitors of Acyl CoA:cholesterol O-Acyltransferase. Chem Pharm Bull;49:830-839.
    • (2001) Chem Pharm Bull , vol.49 , pp. 830-839
    • Ohishi, K.1    Aiyama, R.2    Hatano, H.3    Yoshida, Y.4    Wada, Y.5    Yokai, W.6    Sawada, H.7    Watanabe, T.8    Yokokura, T.9
  • 23
    • 84862128921 scopus 로고    scopus 로고
    • Sulphonate ACAT inhibitors. U. S. Patent 5,510,379, April, 23
    • Lee H.T. (1996) Sulphonate ACAT inhibitors. U. S. Patent 5, 510, 379, April, 23.
    • (1996)
    • Lee, H.T.1
  • 24
    • 84862134496 scopus 로고    scopus 로고
    • Tetrazole Alkyl Amide ACAT Inhibitors. U. S. Patent 5,646,170. July, 8
    • Lee H.T. (1997) Tetrazole Alkyl Amide ACAT Inhibitors. U. S. Patent 5, 646, 170. July, 8.
    • (1997)
    • Lee, H.T.1
  • 25
    • 84862134497 scopus 로고
    • 1,2-Disubstituted Ethyl Amides as Inhibitors of ACAT. WO94/06784, March, 31
    • Dugar S. (1994) 1, 2-Disubstituted Ethyl Amides as Inhibitors of ACAT. WO94/06784, March, 31.
    • (1994)
    • Dugar, S.1
  • 26
    • 84862128922 scopus 로고    scopus 로고
    • beta;-Carboxy Sulfonamide ACAT Inhibitors. U. S. Patent 5,491,170, February, 13
    • Lee H.T., Picard J.A., Sliskovic D.R. (1996) β-Carboxy Sulfonamide ACAT Inhibitors. U. S. Patent 5, 491, 170, February, 13.
    • (1996)
    • Lee, H.T.1    Picard, J.A.2    Sliskovic, D.R.3
  • 27
    • 84862128918 scopus 로고    scopus 로고
    • Phosphonamide ACAT inhibitors. U. S. Patent 6,017,905, January, 25
    • Roark W.H. (2000) Phosphonamide ACAT inhibitors. U. S. Patent 6, 017, 905, January, 25.
    • (2000)
    • Roark, W.H.1
  • 28
    • 84862128916 scopus 로고
    • Amide tetrazole ACAT inhibitors. U. S. Patent 5,461,049, October, 24
    • O'Brien P.M., Sliskovic D.R. (1995) Amide tetrazole ACAT inhibitors. U. S. Patent 5, 461, 049, October, 24.
    • (1995)
    • O'Brien, P.M.1    Sliskovic, D.R.2
  • 29
    • 0027985805 scopus 로고
    • Acyl CoA:cholesterol Acyltransferase (ACAT) inhibitors: synthesis and structure-activity relationship studies of a new series of trisubstituted imidazoles
    • Higley C., Wilde R.G., Maduskuie T.P., Johnson A.L., Pennev P., Billheimer J.T., Robinson C.S., Gillies P.J., Wexler R.R. (1994) Acyl CoA:cholesterol Acyltransferase (ACAT) inhibitors: synthesis and structure-activity relationship studies of a new series of trisubstituted imidazoles. J Med Chem;37:3511-3522.
    • (1994) J Med Chem , vol.37 , pp. 3511-3522
    • Higley, C.1    Wilde, R.G.2    Maduskuie, T.P.3    Johnson, A.L.4    Pennev, P.5    Billheimer, J.T.6    Robinson, C.S.7    Gillies, P.J.8    Wexler, R.R.9
  • 30
    • 0027471259 scopus 로고
    • N-Oleoyl-1,2,3,4- tetrahydroquinolines as confomationally restricted inhibitors of Acyl-CoA: cholesterol Acyl Transferase (ACAT)
    • Dugar S., Clader J.W., Burrier R.E., Kogan T.P. (1993) N-Oleoyl-1, 2, 3, 4- tetrahydroquinolines as confomationally restricted inhibitors of Acyl-CoA: cholesterol Acyl Transferase (ACAT). Bioorg Med Chem Lett;3:571-576.
    • (1993) Bioorg Med Chem Lett , vol.3 , pp. 571-576
    • Dugar, S.1    Clader, J.W.2    Burrier, R.E.3    Kogan, T.P.4
  • 31
    • 0029921270 scopus 로고    scopus 로고
    • Novel 4,4-bis(trifluoromethyl) imidazoles as stereospecific and orally active Acyl CoA: cholesterol Acyltransferase (ACAT) inhibitors and antihypercholesterolemic agents
    • Boswell G.A., Li H.Y., Delucca I., Billheimer J.T., Drummond S., Gillies P.J., Robinson C. (1996) Novel 4, 4-bis(trifluoromethyl) imidazoles as stereospecific and orally active Acyl CoA: cholesterol Acyltransferase (ACAT) inhibitors and antihypercholesterolemic agents. Bioorg Med Chem Lett;6:885-888.
    • (1996) Bioorg Med Chem Lett , vol.6 , pp. 885-888
    • Boswell, G.A.1    Li, H.Y.2    Delucca, I.3    Billheimer, J.T.4    Drummond, S.5    Gillies, P.J.6    Robinson, C.7
  • 32
    • 0037011895 scopus 로고    scopus 로고
    • Pharmacophore mapping of a series of 2,4-diamino-5-deazapteridine inhibitors of Mycobacterium avium complex dihydrofolate reductase
    • Debnath A.K. (2002) Pharmacophore mapping of a series of 2, 4-diamino-5-deazapteridine inhibitors of Mycobacterium avium complex dihydrofolate reductase. J Med Chem;45:41-53.
    • (2002) J Med Chem , vol.45 , pp. 41-53
    • Debnath, A.K.1
  • 33
    • 84862142755 scopus 로고    scopus 로고
    • CL277,082; A novel inhibitor of ACAT catalysed cholesterol esterification and cholesterol absorption
    • Largis E., Wang C., BeVaries V., Schaffe F. (2004) CL277, 082; A novel inhibitor of ACAT catalysed cholesterol esterification and cholesterol absorption. J Lipid Res;45:396-401.
    • (2004) J Lipid Res , vol.45 , pp. 396-401
    • Largis, E.1    Wang, C.2    BeVaries, V.3    Schaffe, F.4
  • 35
    • 79953772942 scopus 로고    scopus 로고
    • Synthesis and c-Met kinase inhibition of 3,5-disubstituted and 3,5,7-trisubstituted quinolines: identification of 3-(4-acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a novel anticancer agent
    • Wang Y., Ai J., Wang Y., Chen Y., Wang L., Liu G., Geng M., Zhang A. (2011) Synthesis and c-Met kinase inhibition of 3, 5-disubstituted and 3, 5, 7-trisubstituted quinolines: identification of 3-(4-acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a novel anticancer agent. J Med Chem;54:2127-2142.
    • (2011) J Med Chem , vol.54 , pp. 2127-2142
    • Wang, Y.1    Ai, J.2    Wang, Y.3    Chen, Y.4    Wang, L.5    Liu, G.6    Geng, M.7    Zhang, A.8
  • 37
    • 84988109729 scopus 로고
    • Atomic physicochemical parameters for three-dimensional structure-directed quantitative structure-activity relationships I. Partition coefficient as a measure of hydrophobicity
    • Ghose A.K., Crippen G. (1986) Atomic physicochemical parameters for three-dimensional structure-directed quantitative structure-activity relationships I. Partition coefficient as a measure of hydrophobicity. J Comp Chem;7:565-577.
    • (1986) J Comp Chem , vol.7 , pp. 565-577
    • Ghose, A.K.1    Crippen, G.2


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