BIOMAT Database Logo BIOMAT Database Logo

3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 6. Trans-6-[2-(substituted-1-naphthyl)ethyl(or ethenyl)]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-ones. 1990

J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Merck Sharp & Dohme Research Laboratories, West Point, Pennsylvania 19486.

A variety of trans-6-[2-(substituted-1-naphthyl)ethyl(or ethenyl)]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-ones were prepared and, upon conversion to their 3,5-dihydroxy carboxylates, were found to have good inhibitory activity against the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase, the rate-determining enzyme in cholesterogenesis. The most active compounds are 2,4,6- and 2,4,7-trichloro derivatives and would be expected to display about the same potency as the standard compactin upon resolution.

UI MeSH Term Description Entries
D009281 Naphthalenes Two-ring crystalline hydrocarbons isolated from coal tar. They are used as intermediates in chemical synthesis, as insect repellents, fungicides, lubricants, preservatives, and, formerly, as topical antiseptics.
D011714 Pyrans Pyran
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002627 Chemistry, Physical The study of CHEMICAL PHENOMENA and processes in terms of the underlying PHYSICAL PHENOMENA and processes. Physical Chemistry,Chemistries, Physical,Physical Chemistries
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical
D019161 Hydroxymethylglutaryl-CoA Reductase Inhibitors Compounds that inhibit HYDROXYMETHYLGLUTARYL COA REDUCTASES. They have been shown to directly lower CHOLESTEROL synthesis. HMG-CoA Reductase Inhibitor,HMG-CoA Reductase Inhibitors,Hydroxymethylglutaryl-CoA Reductase Inhibitor,Statin,Statins, HMG-CoA,Inhibitors, HMG-CoA Reductase,Inhibitors, Hydroxymethylglutaryl-CoA,Inhibitors, Hydroxymethylglutaryl-Coenzyme A,Statins,HMG CoA Reductase Inhibitor,HMG CoA Reductase Inhibitors,HMG-CoA Statins,Hydroxymethylglutaryl CoA Reductase Inhibitor,Hydroxymethylglutaryl CoA Reductase Inhibitors,Hydroxymethylglutaryl-CoA Inhibitors,Hydroxymethylglutaryl-Coenzyme A Inhibitors,Inhibitors, HMG CoA Reductase,Inhibitors, Hydroxymethylglutaryl CoA,Inhibitors, Hydroxymethylglutaryl Coenzyme A,Inhibitors, Hydroxymethylglutaryl-CoA Reductase,Reductase Inhibitor, Hydroxymethylglutaryl-CoA,Reductase Inhibitors, HMG-CoA,Reductase Inhibitors, Hydroxymethylglutaryl-CoA,Statins, HMG CoA
D066298 In Vitro Techniques Methods to study reactions or processes taking place in an artificial environment outside the living organism. In Vitro Test,In Vitro Testing,In Vitro Tests,In Vitro as Topic,In Vitro,In Vitro Technique,In Vitro Testings,Technique, In Vitro,Techniques, In Vitro,Test, In Vitro,Testing, In Vitro,Testings, In Vitro,Tests, In Vitro,Vitro Testing, In

Related Publications

J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Inhibitors of cholesterol biosynthesis. 4. trans-6-[2-(substituted-quinolinyl)ethenyl/ethyl]tetrahydro-4-hydroxy-2 H-pyran-2-ones, a novel series of HMG-CoA reductase inhibitors.
January 1991, Journal of medicinal chemistry,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Inhibitors of cholesterol biosynthesis. 6. trans-6-[2-(2-N-heteroaryl-3,5-disubstituted- pyrazol-4-yl)ethyl/ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones.
May 1992, Journal of medicinal chemistry,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
(2RS,5SR,6SR)-methyl 4-{cis-2-[3-fluoro-5-(4-methoxy-3,4,5,6-tetrahydro-2H-pyran-4-yl)phenoxymethyl]-6-hydroxy-3-phenylmorpholino}benzenesulfinate.
February 2006, Acta crystallographica. Section C, Crystal structure communications,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Structure of a lactone, (3 alpha,4 alpha,6 alpha)-4-(tert- butyldimethylsiloxy)-3,4,5,6-tetrahydro-6-methyl-3-(2-oxopropyl)- 2H- pyran-2-one.
November 1991, Acta crystallographica. Section C, Crystal structure communications,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues.
May 2005, Bioorganic & medicinal chemistry letters,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Tachyphylaxis in 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors.
April 2001, The American journal of cardiology,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Falls and 3-hydroxy-3-methylglutaryl coenzyme a reductase inhibitors.
November 2002, Archives of internal medicine,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Pleiotropic effects of 3-hydroxy-3-methylglutaryl coenzyme a reductase inhibitors.
November 2001, Arteriosclerosis, thrombosis, and vascular biology,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Clinical pharmacokinetics of 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors.
November 1996, Clinical pharmacokinetics,
J D Prugh, and A W Alberts, and A A Deana, and J L Gilfillian, and J W Huff, and R L Smith, and J M Wiggins
Antileukemic properties of 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors.
December 2013, Leukemia & lymphoma,
Copied contents to your clipboard!