메뉴 건너뛰기




Volumn 36, Issue 11, 1993, Pages 1630-1640

Structure-Activity Relationship of N-[2-(Dimethylamino)-6-[3-(5-methyl-4-phenyl-1H-imidazol-1-yl)propoxy]phenyl]-N′-pentylurea and Analogues. Novel Potent Inhibitors of Acyl-CoA:Cholesterol O-Acyltransferase with Antiatherosclerotic Activity

Author keywords

[No Author keywords available]

Indexed keywords

ACYLTRANSFERASE INHIBITOR; CHOLESTEROL ACYLTRANSFERASE; N [2 (DIMETHYLAMINO) 6 [3 (5 METHYL 4 PHENYL 1H IMIDAZOL 1 YL)PROPOXY]PHENYL] N' PENTYLUREA; N BUTYL N' [2 (DIMETHYLAMINO) 6 [3 (4 PHENYL 1H IMIDAZOL 1 YL)PROPOXY]PHENYL]UREA; UNCLASSIFIED DRUG;

EID: 0027270448     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00063a013     Document Type: Article
Times cited : (30)

References (38)
  • 1
    • 0021524498 scopus 로고
    • How LDL Receptors Influence Cholesterol and Atherosclerosis
    • Brown, M. S.; Goldsteine, J. L. How LDL Receptors Influence Cholesterol and Atherosclerosis. Sci. Am. 1984, 251, 52–60.
    • (1984) Sci. Am. , vol.251 , pp. 52-60
    • Brown, M.S.1    Goldsteine, J.L.2
  • 2
    • 0002877405 scopus 로고
    • Cholesterol Ester Metabolism
    • Goodman, D. S. Cholesterol Ester Metabolism. Physiol. Rev. 1965, 45, 747–839.
    • (1965) Physiol. Rev. , vol.45 , pp. 747-839
    • Goodman, D.S.1
  • 3
    • 0022256566 scopus 로고
    • Role of Acyl-CoA:Cholesterol Acyltransferase in Cellular Cholesterol Metabolism
    • Suckling, K. E.; Stange, E. F. Role of Acyl-CoA:Cholesterol Acyltransferase in Cellular Cholesterol Metabolism. J. Lipid Res. 1985, 26, 647–671.
    • (1985) J. Lipid Res. , vol.26 , pp. 647-671
    • Suckling, K.E.1    Stange, E.F.2
  • 4
    • 0020581405 scopus 로고
    • β-Sitosterol: Esterification by Intestinal Acylcoenzyme A: Cholesterol Acyltransferase (ACAT) and Its Effect on Cholesterol Esterification
    • Field, F. J.; Mathur, S. N. β-Sitosterol: Esterification by Intestinal Acylcoenzyme A: Cholesterol Acyltransferase (ACAT) and Its Effect on Cholesterol Esterification. J. Lipid Res. 1983, 24, 409–417.
    • (1983) J. Lipid Res. , vol.24 , pp. 409-417
    • Field, F.J.1    Mathur, S.N.2
  • 5
    • 0019430455 scopus 로고
    • Acyl-CoA:Cholesterol Acyltransferase in Human Small Intestine: Its Activity and Some Properties of the Enzyme Reaction
    • Helgerud, P.; Saarem, K.; Norum, K. R. Acyl-CoA:Cholesterol Acyltransferase in Human Small Intestine: Its Activity and Some Properties of the Enzyme Reaction. J. Lipid Res. 1981, 22, 271–277.
    • (1981) J. Lipid Res. , vol.22 , pp. 271-277
    • Helgerud, P.1    Saarem, K.2    Norum, K.R.3
  • 6
    • 0024389312 scopus 로고
    • CL 277,082: a Novel Inhibitor of ACAT-Catalyzed Cholesterol Esterification and Cholesterol Absorption
    • Largis, E. E.; Wang, C. H.; De Vries, V. G.; Schaffer, S. A. CL 277,082: a Novel Inhibitor of ACAT-Catalyzed Cholesterol Esterification and Cholesterol Absorption. J. Lipid Res. 1989, 30, 681–690.
    • (1989) J. Lipid Res. , vol.30 , pp. 681-690
    • Largis, E.E.1    Wang, C.H.2    De Vries, V.G.3    Schaffer, S.A.4
  • 7
    • 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. Role of Acyl-CoA: Cholesterol Acyltransferase in Cholesterol Absorption and Its Inhibition by 57–118 in the Rabbit. J. Lipid Res. 1983, 24, 1127–1134.
    • (1983) J. Lipid Res. , vol.24 , pp. 1127-1134
    • Heider, J.G.1    Pickens, C.E.2    Kelly, L.A.3
  • 8
    • 0018377937 scopus 로고
    • Cholesterol Esterification and Cholesterol Ester Accumulation in Cultured Pigeon and Monkey Arterial Smooth Muscle Cells
    • Smith, B. P.; St. Clair, R. W.; Lewis, J. C. Cholesterol Esterification and Cholesterol Ester Accumulation in Cultured Pigeon and Monkey Arterial Smooth Muscle Cells. Exp. Mol. Pathol. 1979, 30, 190–208.
    • (1979) Exp. Mol. Pathol. , vol.30 , pp. 190-208
    • Smith, B.P.1    St. Clair, R.W.2    Lewis, J.C.3
  • 9
    • 0017652990 scopus 로고
    • Stimulation of Acyl-CoA:Cholesterol Acyltransferase Activity by Hyperlipemic Serum Lipoproteins (39838)
    • Rothblat, G. H.; Naftulin, M.; Arbogast, L. Y. Stimulation of Acyl-CoA:Cholesterol Acyltransferase Activity by Hyperlipemic Serum Lipoproteins (39838). Proc. Soc. Exp. Biol. Med. 1977, 155, 501–506.
    • (1977) Proc. Soc. Exp. Biol. Med. , vol.155 , pp. 501-506
    • Rothblat, G.H.1    Naftulin, M.2    Arbogast, L.Y.3
  • 10
    • 0019162068 scopus 로고
    • The Cholesterol Ester Cycle in Macrophage Foam Cells
    • Brown, M. S.; Ho, Y. K.; Goldsteine, J. L. The Cholesterol Ester Cycle in Macrophage Foam Cells. J. Biol. Chem. 1980, 255, 9344–9352.
    • (1980) J. Biol. Chem. , vol.255 , pp. 9344-9352
    • Brown, M.S.1    Ho, Y.K.2    Goldsteine, J.L.3
  • 11
  • 12
    • 0017819460 scopus 로고
    • Stimulation of Esterified Cholesterol Accumulation in Tissue Culture Cells Exposed to High Density Lipoproteins Enriched in Free Cholesterol
    • Rothblat, G. H.; Arbogast, L. Y.; Ray, E. K. Stimulation of Esterified Cholesterol Accumulation in Tissue Culture Cells Exposed to High Density Lipoproteins Enriched in Free Cholesterol. J. Lipid Res. 1978, 19, 350–358.
    • (1978) J. Lipid Res. , vol.19 , pp. 350-358
    • Rothblat, G.H.1    Arbogast, L.Y.2    Ray, E.K.3
  • 13
    • 0015917210 scopus 로고
    • Esterification of Cholesterol by Homogenates of Atherosclerotic and Normal Aortas
    • Hashimoto, S.; Dayton, S.; Alfine-slater, R. B. Esterification of Cholesterol by Homogenates of Atherosclerotic and Normal Aortas. Life Sci. 1973, 12, 1–11.
    • (1973) Life Sci. , vol.12 , pp. 1-11
    • Hashimoto, S.1    Dayton, S.2    Alfine-slater, R.B.3
  • 14
    • 0014835942 scopus 로고
    • Influence of Duration of Cholesterol Feeding on Esterification of Fatty Acids by Cell-Free Preparation of Pigeon Aorta
    • St. Clair, R. W.; Lofland, H. B.; Clarkson, T. B. Influence of Duration of Cholesterol Feeding on Esterification of Fatty Acids by Cell-Free Preparation of Pigeon Aorta. Circ. Res. 1970, 27, 213–225.
    • (1970) Circ. Res. , vol.27 , pp. 213-225
    • St. Clair, R.W.1    Lofland, H.B.2    Clarkson, T.B.3
  • 15
    • 0019188967 scopus 로고
    • Properties of Acyl-CoA:Cholesterol O-Acyltransferase in Aortic Microsomes from Atherosclerotic Rabbits
    • Brecher, P.; Chan, C. T. Properties of Acyl-CoA:Cholesterol O-Acyltransferase in Aortic Microsomes from Atherosclerotic Rabbits. Biochim. Biophys. Acta 1980, 617, 458–471.
    • (1980) Biochim. Biophys. Acta , vol.617 , pp. 458-471
    • Brecher, P.1    Chan, C.T.2
  • 16
    • 0025756150 scopus 로고
    • Therapeutic Potential of ACAT Inhibitors as Lipid Lowering and Anti-atherosclerotic Agents
    • Sliskovic, D. R.; White, A. D. Therapeutic Potential of ACAT Inhibitors as Lipid Lowering and Anti-atherosclerotic Agents. Trends Pharmacol. Sci. 1991, 12, 194–199.
    • (1991) Trends Pharmacol. Sci. , vol.12 , pp. 194-199
    • Sliskovic, D.R.1    White, A.D.2
  • 17
    • 0025734242 scopus 로고
    • Synthesis and Hypocholesterolemic Activity of 6,7-Dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-diones, Novel Inhibitors of Acyl-CoA:Cholesterol O-Acyltransferase
    • Larsen, S. D.; Spilman, C. H.; Bell, F. P.; Dinh, D. M.; Martineborough, E.; Wilson, G. J. Synthesis and Hypocholesterolemic Activity of 6,7-Dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-diones, Novel Inhibitors of Acyl-CoA:Cholesterol O-Acyltransferase. J. Med. Chem. 1991, 34, 1721–1727.
    • (1991) J. Med. Chem. , vol.34 , pp. 1721-1727
    • Larsen, S.D.1    Spilman, C.H.2    Bell, F.P.3    Dinh, D.M.4    Martineborough, E.5    Wilson, G.J.6
  • 18
    • 0024989838 scopus 로고
    • Antiatherosclerotic Agents. A Structurally Novel Bivalent Inhibitor of Acyl-CoA:Cholesterol O-Acyltransferase with Systemic Activity
    • Gammill, R. B.; Bell, F. P.; Bell, L. T.; Bisaha, S. N.; Wilson, G. J. Antiatherosclerotic Agents. A Structurally Novel Bivalent Inhibitor of Acyl-CoA:Cholesterol O-Acyltransferase with Systemic Activity. J. Med. Chem. 1990, 33, 2685–2687.
    • (1990) J. Med. Chem. , vol.33 , pp. 2685-2687
    • Gammill, R.B.1    Bell, F.P.2    Bell, L.T.3    Bisaha, S.N.4    Wilson, G.J.5
  • 19
    • 0024463802 scopus 로고
    • Potential Antiatherosclerotic Agents. 6. Hypocholesterolemic Trisubstituted Urea Analogues
    • De Vries, V. G.; Bloom, J. D.; Dutia, M. D.; Katocs, A. S.; Largies, E. E. Potential Antiatherosclerotic Agents. 6. Hypocholesterolemic Trisubstituted Urea Analogues. J. Med. Chem. 1989, 32, 2318–2325.
    • (1989) J. Med. Chem. , vol.32 , pp. 2318-2325
    • De Vries, V.G.1    Bloom, J.D.2    Dutia, M.D.3    Katocs, A.S.4    Largies, E.E.5
  • 20
    • 0024394844 scopus 로고
    • Effects of MK-733 (Simvastatine), an Inhibitor of 3-Hydroxy-3-methylglutaryl CoenzymeA Reductase, on Intestinal AcylcoenzymeA:Cholesterol Acyltrasferase Activity in Rabbits
    • Ishida, F.; Sato, A.; Iizuka, Y.; Kitani, K.; Sawasaki, Y.; Kamei, T. Effects of MK-733 (Simvastatine), an Inhibitor of 3-Hydroxy-3-methylglutaryl CoenzymeA Reductase, on Intestinal AcylcoenzymeA:Cholesterol Acyltrasferase Activity in Rabbits. Biochim. Biophys. Acta 1989, 1004, 117–123.
    • (1989) Biochim. Biophys. Acta , vol.1004 , pp. 117-123
    • Ishida, F.1    Sato, A.2    Iizuka, Y.3    Kitani, K.4    Sawasaki, Y.5    Kamei, T.6
  • 21
    • 0023831386 scopus 로고
    • Antiatherosclerotic and Antihyperlipidemic Effects of Octimibate Sodium in Rabbits
    • Rucker, W.; Prop, G.; Huther, A. M. Antiatherosclerotic and Antihyperlipidemic Effects of Octimibate Sodium in Rabbits. Atherosclerosis 1988, 69, 155–160.
    • (1988) Atherosclerosis , vol.69 , pp. 155-160
    • Rucker, W.1    Prop, G.2    Huther, A.M.3
  • 23
    • 0023028820 scopus 로고
    • Mechanism of the Inhibition of Cholesterol Absorption by DL-Melinamide: Inhibition of Cholesterol Esterification
    • Natori, K.; Okazaki, Y.; Nakajima, J.; Hirohoshi, T.; Aono, S. Mechanism of the Inhibition of Cholesterol Absorption by DL-Melinamide: Inhibition of Cholesterol Esterification. Jpn. J. Pharmacol. 1986, 42, 517–523.
    • (1986) Jpn. J. Pharmacol. , vol.42 , pp. 517-523
    • Natori, K.1    Okazaki, Y.2    Nakajima, J.3    Hirohoshi, T.4    Aono, S.5
  • 24
    • 0022535558 scopus 로고
    • Potential Antiatherosclerotic Agents. 5. An Acyl-CoA:Cholesterol O-Acyltransferase Inhibitor with Hypocholesterolemic Activity
    • De Vries, V. G.; Schaffer, S. A.; Largis, E. E.; Dutia, M. D.; Wang, C.; Bloom, J. D.; Katocs, A. S. Potential Antiatherosclerotic Agents. 5. An Acyl-CoA:Cholesterol O-Acyltransferase Inhibitor with Hypocholesterolemic Activity. J. Med. Chem. 1986, 29, 1131–1133.
    • (1986) J. Med. Chem. , vol.29 , pp. 1131-1133
    • De Vries, V.G.1    Schaffer, S.A.2    Largis, E.E.3    Dutia, M.D.4    Wang, C.5    Bloom, J.D.6    Katocs, A.S.7
  • 25
    • 0022633743 scopus 로고
    • Chloropromazine Inhibits Arterial ACAT and Reduces Arterial Cholesterol and Cholesteryl Ester Accumulation in Cholesterol-fed Rabbits
    • Bell, F. P.; Schaub, R. G. Chloropromazine Inhibits Arterial ACAT and Reduces Arterial Cholesterol and Cholesteryl Ester Accumulation in Cholesterol-fed Rabbits. Arteriosclerosis 1986, 6, 42–49.
    • (1986) Arteriosclerosis , vol.6 , pp. 42-49
    • Bell, F.P.1    Schaub, R.G.2
  • 26
    • 0005453972 scopus 로고
    • CL277,082, a Novel Inhibitor of Cholesterol Esterification and Cholesterol Absorption
    • Fidge, N. H., Nestel, P. J., Eds.; Elsevier Science Publishers BV: Amsterdam
    • Schaffer, S. A.; Bloom, J. D.; De Vries, V. G.; Dutia, M.; Katocs, A. S., Jr.; Largis, E. E. CL277,082, a Novel Inhibitor of Cholesterol Esterification and Cholesterol Absorption. In Atherosclerosis VII; Fidge, N. H., Nestel, P. J., Eds.; Elsevier Science Publishers BV: Amsterdam, 1986, pp 633–636.
    • (1986) Atherosclerosis VII , pp. 633-636
    • Schaffer, S.A.1    Bloom, J.D.2    De Vries, V.G.3    Dutia, M.4    Katocs, A.S.5    Largis, E.E.6
  • 27
    • 0026347265 scopus 로고
    • Comparison of CI-976, an ACAT Inhibitor, and Selected Lipid-Lowering Agents for Antiatherosclerotic Activity in Iliac-Femoral and Thoracic Aortic Lesions
    • Bocan, T. M. A.; Mueller, S. B.; Uhlendorf, P. D.; Newton, R. S.; Krause, B. R. Comparison of CI-976, an ACAT Inhibitor, and Selected Lipid-Lowering Agents for Antiatherosclerotic Activity in Iliac-Femoral and Thoracic Aortic Lesions. Arteriosclerosis Thrombosis 1991, 11, 1830–1843.
    • (1991) Arteriosclerosis Thrombosis , vol.11 , pp. 1830-1843
    • Bocan, T.M.A.1    Mueller, S.B.2    Uhlendorf, P.D.3    Newton, R.S.4    Krause, B.R.5
  • 28
    • 85022486627 scopus 로고    scopus 로고
    • Unpublished results
    • Kimura, T.; et al. Unpublished results.
    • Kimura, T.1
  • 29
    • 85022549530 scopus 로고    scopus 로고
    • max values were 3173 and 2069 ng/mL (4), 1671 and 1276 ng/mL (13), 202 and 161 ng/mL (14), 1920 and 508 ng/mL (24), <30 ng/mL (28, 29, 31, and 37), and 355 and 202 ng/mL (30), Unpublished results
    • max values were 3173 and 2069 ng/mL (4), 1671 and 1276 ng/mL (13), 202 and 161 ng/mL (14), 1920 and 508 ng/mL (24), <30 ng/mL (28, 29, 31, and 37), and 355 and 202 ng/mL (30). Nose, K.; et al. Unpublished results.
    • Nose, K.1
  • 32
    • 0010114968 scopus 로고
    • An Improved Synthesis of 5-Substituted Tetrazoles
    • Finnegan, W. G.; Henry, R. A.; Lofquist, R. An Improved Synthesis of 5-Substituted Tetrazoles. J. Am. Chem. Soc. 1958, 80, 3908–3911.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3908-3911
    • Finnegan, W.G.1    Henry, R.A.2    Lofquist, R.3
  • 33
    • 33947294224 scopus 로고
    • Protection by Acylation in the Selective Alkylation of Heterocycles
    • Olofson, R. A.; Kendall, R. V. Protection by Acylation in the Selective Alkylation of Heterocycles. J. Org. Chem. 1970, 35, 2246–2248.
    • (1970) J. Org. Chem. , vol.35 , pp. 2246-2248
    • Olofson, R.A.1    Kendall, R.V.2
  • 34
    • 85022490072 scopus 로고
    • The Tautomerism of Diphenyl[5(4)-phenyl-1H-1,2,3-triazol-4(5)-yl]-methanol. A Carbon-13 Nuclear Magnetic Study
    • Avendano, C.; Gomenz-Molinero, E.; Pascual, C.; Elgueo, J. The Tautomerism of Diphenyl[5(4)-phenyl-1H-1,2,3-triazol-4(5)-yl]-methanol. A Carbon-13 Nuclear Magnetic Study. J. Chem. Res. Synop. 1986, 2, 78–79.
    • (1986) J. Chem. Res. Synop. , vol.2 , pp. 78-79
    • Avendano, C.1    Gomenz-Molinero, E.2    Pascual, C.3    Elgueo, J.4
  • 35
    • 0009677753 scopus 로고
    • Methylation of 5-Phenyltetrazole
    • Henry, R. A. Methylation of 5-Phenyltetrazole. J. Am. Chem. Soc. 1951, 73, 4470.
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 4470
    • Henry, R.A.1
  • 37
    • 0024293218 scopus 로고
    • Chemical Modification of Acyl-CoA:Cholesterol O-Acyltransferase. 1. Identification of Acyl-CoA:Cholesterol O-Acyltransferase Subtypes by Differential Diethyl Pyrocarbonate Sensitivity
    • Kinnunen, P. M.; DeMichele, A.; Lange, L. G. Chemical Modification of Acyl-CoA:Cholesterol O-Acyltransferase. 1. Identification of Acyl-CoA:Cholesterol O-Acyltransferase Subtypes by Differential Diethyl Pyrocarbonate Sensitivity. Biochemistry 1988, 27, 7344–7350.
    • (1988) Biochemistry , vol.27 , pp. 7344-7350
    • Kinnunen, P.M.1    DeMichele, A.2    Lange, L.G.3
  • 38
    • 84996297290 scopus 로고
    • Ariens, E. J., Ed.; Academic Press: New York
    • Verloop, A.; Hoogenstraaten, M.; Tipker, J. Drug Design; Ariens, E. J., Ed.; Academic Press: New York, 1976, Vol. VII, pp 180–185.
    • (1976) Drug Design , vol.7 , pp. 180-185
    • Verloop, A.1    Hoogenstraaten, M.2    Tipker, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.