Synthesis and hypolipidemic activities of novel 2-[4-[(diethoxyphosphoryl)methyl]phenyl]quinazolines and 4(3H)-quinazolinones

Journal of Medicinal Chemistry

Volumn 39, Issue 7, 1996, Pages 1433-1437

  Kurogi, Yasuhisa ^a   Inoue, Yasuhide ^a   Tsutsumi, Kazuhiko ^a   Nakamura, Shizuo ^a   Nagao, Kazushi ^a   Yoshitsugu, Hiroki ^a   Tsuda, Yoshihiko ^a  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 [(DIETHOXYPHOSPHORYL)METHYL]PHENYL] 3 METHYL 4(3H) QUINAZOLINONE; 2 [4 [(DIETHOXYPHOSPHORYL)METHYL]PHENYL] 4 METHOXYQUINAZOLINE; 4 [(4 BROMO 2 CYANOPHENYL)CARBAMOYL]BENZYLPHOSPHONIC ACID DIETHYL ESTER; ANTILIPEMIC AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHOLESTEROL BLOOD LEVEL; DRUG EFFECT; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME ACTIVITY; HYPERLIPIDEMIA; HYPOLIPEMIA; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTILIPEMIC AGENTS; ARTERIOSCLEROSIS; BENZAMIDES; BIOLOGICAL AVAILABILITY; CHOLESTEROL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYPERLIPIDEMIAS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; POLYETHYLENE GLYCOLS; QUINAZOLINES; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; TRIGLYCERIDES;

EID: 0029881470     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9506938     Document Type: Article

References (19)

1. Larsen, S. D.; Spilman, C. H. New Potential Therapies for the Treatment of Atherosclerosis. Annu. Rep. Med. Chem. 1993, 28, 217-225.
2. 2-like Particles during Lipolysis of Very Low Density Lipoproteins in vitro. Proc. Natl. Acad. Sci. U.SA. 1978, 75, 4519-4523.
3. Tsutsumi, K.; Inoue, Y.; Shima, A.; Iwasaki, K.; Kawamura, M.; Murase, T. The Novel Compound NO-1886 Increase Lipoprotein Lipase Activity with Resulting Elevation of High Density Lipoprotein Cholesterol, and Long-term Administration Inhibits Atherogenesis in the Coronary Arteries of Rats with Experimental Atherosclerosis. J. Clin. Invest. 1993, 92, 411-417.
4. Fenton, G.; Newton, G. C.; Wyman, M. B.; Bagge, P.; Dron, D. I.; Riddell, D.; Jones, D. G. Hypolipidemic 2-[4-(1,1-Dimethylethyl)phenyl]-4H-3,1-benzoxazin-4-ones. Structure-Activity Relationships of a Novel Series of High-Density Lipoprotein Elevators. J. Med. Chem. 1989, 32, 265-272.
5. Curd, F. H.; Landquist, J K.; Rose, F. L. Synthetic Antimalarials. Part XIV. Some 2-Arylamino-4-aminoalkylaminoquinazolines. J. Chem. Soc. 1994, 775-783.
6. Parmar, S. S.; Singh, S. P. Synthesis of Substituted 2-Methyl-3-(3,4-dimethoxy/dihydroxyphenylethyl)4-quinazolines as Possible AntiParkinson Drugs. J. Heterocycl. Chem. 1979, 16, 449-452.
7. Methaqualone The Merck Index, 11th ed.; Merck and Co., Inc.: Rahway, NJ, 1989; pp 939-940.
8. Wolfe, J. F.; Rathman, T. L.; Sleevi, M. C ; Campbell, J. A.; Greenwood, T. D. Synthesis and Anticonvulsant Activity of Some New 2-Substituted 3-Aryl-4(3H)-quinazolines. J. Med. Chem. 1990, 33, 161-166.
9. Jiang, J. B.; Hesson, D. P.; Dusak, B. A.; Dexter, D. L.; Kang, G. J.; Hamel, E. Synthesis and Biological Evaluation of 2-Styrylquinazolin-4(3H)-ones, a New Class of Antimitotic Anticancer Agents Which Inhibit Tubulin Polymerization. J. Med. Chem. 1990, 33, 1721-1728.
10. Hori, M.; Iemura, R.; Hara, H.; Ozaki, A.; Sukamoto, T.; Ohtaka, H. Novel 4-Substituted 2-piperazinylquinazolines as Potent Anticonvulsive and Antihypoxic Agents. Chem. Pharm. Bull. 1990, 38, 1286-1291.
11. 1-Adrenergic blocker). The Merck Index, 11th ed.; Merck and Co., Inc.: Rahway, NJ, 1989; pp 1222-1223.
12. (b) Levin, J. I.; Aranapakam, M. V. New quinazolinone derivatives are angiotensin II antagonists - for treating hypertension and congestive heart failure. U.S. Patent 5284853-A, 1993.
13. (a) Bloom, S. M.; Rochester, N. Y.; Hill, J. A. Preparation of Symmetrically and Unsymmetrically Substituted Stilbenebisbenzoxazoles. U.S. Patent 3-086-673, 1971.
14. (b) Bellucci, C.; Gualtieri, F.; Chiarini, A. Negative inotropic activity of parasubstituted diethyl benzylphosphonates related to fostedil. Eur. J. Med. Chem. 1987, 22, 473-477.
15. Breukink, K. W.; Krol, L. H.; Verkade, P. E.; Wepster, B. M. Preparation of Quinazoline Derivatives through Ring-closure of Aromatic ortho-cyano-acylamino Compounds in Alkaline Alcoholic or Phenolic Medium. RECUEIL 1957, 76, 401-414.
16. McKee, R. L.; McKee, M. K.; Bost, R. W. Some Basically Substituted Quinazolines. J. Am. Chem. Soc. 1946, 68, 1902-1903.
17. Hulshoff, A.; Perrin, J. H. A Comparison of the Determination of Partition Coefficients of 1,4-Beazodiazepines by High-Performance Liquid Chromatography and Thin-layer Chromatography. J. Chromatogr. 1976, 129, 263-276. Henry, D.; Block, J. H.; Anderson, J. L.; Carlson, G. R. Use of High-Performance Liquid Chromatography for Quantitative Structure-Activity Relationship Studies of Sulfonamides and Barbiturates. J. Med. Chem. 1976, 5, 619-626.
18. Hulshoff, A.; Perrin, J. H. A Comparison of the Determination of Partition Coefficients of 1,4-Beazodiazepines by High-Performance Liquid Chromatography and Thin-layer Chromatography. J. Chromatogr. 1976, 129, 263-276. Henry, D.; Block, J. H.; Anderson, J. L.; Carlson, G. R. Use of High-Performance Liquid Chromatography for Quantitative Structure-Activity Relationship Studies of Sulfonamides and Barbiturates. J. Med. Chem. 1976, 5, 619-626.
19. Kuroda, M.; Tanzawa, K.; Tsujita, Y.; Endo, A. Mechanism for Elevation of Hepatic Cholesterol Synthesis and Serum Cholesterol Levels in Triton WR-1339-induced Hyperlipidemia. Biochim. Biophys. Acta 1977, 489, 119-125.