79952-42-4

Usage

Uses

Used in Pharmaceutical Industry:
6(R)-[2-(8(S)-Hydroxy]-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl]ethyl-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one is used as an intermediate in the synthesis of hypolipidemic drugs, such as Simvastatin and Lovastatin analogs. These drugs are known for their cholesterol-lowering properties, making them valuable in the treatment and management of hyperlipidemia and related cardiovascular conditions.
Used in Drug Development:
Due to its unique chemical properties and potential biological activities, 6(R)-[2-(8(S)-Hydroxy]-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl]ethyl-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one may also be explored for its potential use in drug development. Its hydroxy substituent at position 8 could be exploited for the design of new pharmaceutical agents targeting various therapeutic areas, such as cardiovascular, metabolic, or neurological disorders.
Used in Chemical Research:
As a complex polyketide, 6(R)-[2-(8(S)-Hydroxy]-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl]ethyl-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one may also serve as a valuable compound for chemical research. Its unique structure and properties can be studied to gain insights into the synthesis, reactivity, and potential applications of similar polyketide compounds in various fields, including pharmaceuticals, materials science, and agrochemistry.

InChI:InChI=1/C19H28O4/c1-11-7-13-4-3-12(2)16(19(13)17(21)8-11)6-5-15-9-14(20)10-18(22)23-15/h3-4,7,11-12,14-17,19-21H,5-6,8-10H2,1-2H3/t11?,12-,14+,15+,16-,17?,19-/m0/s1

Upstream product

• 75330-75-5 lovastatin 
• 75225-51-3 lovastatin acid 
• 86827-77-2 4a,5-dihydromonacolin L 
• 1298116-19-4 4a,5-dihydromonacolin L lithium salt 
• 108-24-7 acetic anhydride 
• 132748-10-8 (3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid 

Downstream Products

• 1431473-49-2 (1S,3R,7S,8S,8αR)-8-(2-((2R,4R)-4-((tert-butyldimethylchlorosilane)oxy)-6-oxohexahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8α-hexahydronaphthalene-1-yl(4-nitrophenyl)carbonate 
• 1431473-53-8 C₄₂H₆₂N₄O₇Si 
• 1431473-52-7 C₄₁H₆₀N₄O₇Si 
• 1431473-55-0 (4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-[((4-{1-[7-(hydroxyamino)-7-oxoheptyl]-1H-1,2,3-triazol-4-yl}benzyl)carbamoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 1431473-54-9 (4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-[((4-{1-[7-(hydroxyamino)-7-oxoheptyl]-1H-1,2,3-triazol-4-yl}phenyl)carbamoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 1431473-51-6 (4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-[((4-ethynylbenzyl)carbamoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 1431473-50-5 (4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-[((4-ethynylphenyl)carbamoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 123049-81-0 simvastatin 
• 1002347-71-8 C₂₅H₃₂⁽²⁾H₆O₅ 
• 1335460-29-1 C₃₁H₄₆⁽²⁾H₆O₅Si 
• 210980-68-0 anhydrosimvastatin 
• 145576-25-6 simvastatin acetate 
• 851402-85-2 bis-simvastatin 
• 851402-84-1 4-simvastain-8-lovastatin 

Relevant academic research and scientific papers

HMG-COA REDUCTASE DEGRADATION INDUCING COMPOUND

The present invention relates HMG-CoA reductase degradation inducing compounds. Specifically, the present invention relates a bifunctional compound in which a HMG-CoA reductase binding moiety and an E3 ubiquitin ligase-binding moiety are linked by a chemical linker. The present invention also relates a method for preparing the compounds, and a method for degradation of HMG-CoA reducatase using the compounds, as well as use for prevention or treatment of HMG-CoA reductase related diseases using the compounds.

A compound targeting ubiquitination degradation HMGCR or a pharmaceutically acceptable salt thereof. Preparation method and application

The invention relates to a compound of targeted ubiquitination degradation HMGCR or a pharmaceutically acceptable salt thereof as well as a preparation method and application thereof. The structure is shown in the general formula (I). The compound or the

Hydroxy methyl glutaryl coenzyme A reductase inhibitors

The invention relates to a compound, in particular to an HMG-GoA reductase inhibitor. The HMG-GoA reductase inhibitor is ester formed by naphthol and Cn polyhydroxyalkanoate or Cn olefine acid of the compound in the formula I, wherein n is an integer from six to fourteen. The compound can be effectively used for treating or preventing dyslipidemia, for example, the compound can effectively treat or prevent hypercholesteremia or mixed type hyperlipidemia.

Synthesis and biological evaluation of lovastatin-derived aliphatic hydroxamates that induce reactive oxygen species

Some hydroxamate compounds induce cancer cell death by intracellular reactive oxygen species (ROS). This study introduced the hydroxamate core into lovastatin, a fungus metabolite clinically used for the treatment of hypercholesterolemia. The resulting co

DUAL ACTION INHIBITORS AGAINST HISTONE DEACETYLASES AND 3-HYDROXY-3-METHYLGLUTARYL COENZYME A REDUCTASE

Disclosed herein are novel compounds of formula (I), and uses thereof. The compounds of Formula (I) are inhibitors of histone deacetylases (HDACs) and 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase (HMGR). Also provided are methods of using the

HYPOCHOLESTEROLEMIC, ANTI-INFLAMMATORY AND ANTIEPILEPTIC NEUROPROTECTIVE COMPOUND

The present invention describes a compound of formula (I) its hydroxy acid form, the pharmaceutically acceptable salts of said hydroxy acid and pharmaceutically acceptable prodrugs and solvates of the compound and of its hydroxy acid form and, in particular, said compound, its hydroxy acid form, salts, etc. for use in the prevention of: neurodegenerative diseases, cognitive impairment, diseases associated with undesired oxidation, age-associated pathological processes and progeria, cardiovascular diseases such as atherosclerosis, atrial fibrillation, dyslipidemia, hypercholesterolemia, hyperlipidemia, and hypertriglyceridemia, inflammation or inflammatory processes, or epilepsy, epileptic seizures and convulsions.

Design and synthesis of dual-action inhibitors targeting histone deacetylases and 3-hydroxy-3-methylglutaryl coenzyme a reductase for cancer treatment

A series of dual-action compounds were designed to target histone deacetylase (HDAC) and 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR) by having a hydroxamate group essential for chelation with the zinc ion in the active site of HDAC and the key structural elements of statin for binding with both proteins. In our study, the statin hydroxamic acids prepared by a fused strategy are most promising in cancer treatments. These compounds showed potent inhibitory activities against HDACs and HMGR with IC50 values in the nanomolar range. These compounds also effectively reduced the HMGR activity as well as promoted the acetylations of histone and tubulin in cancer cells, but were not toxic to normal cells.

HYPOCHOLESTEROLEMIC, ANTI-INFLAMMATORY AND ANTIEPILEPTIC NEUROPROTECTIVE COMPOUND

The present invention describes a compound of formula (I) its hydroxy acid form, the pharmaceutically acceptable salts of said hydroxy acid and pharmaceutically acceptable prodrugs and solvates of the compound and of its hydroxy acid form and, in particular, said compound, its hydroxy acid form, salts, etc. for use in the prevention of: neurodegenerative diseases, cognitive impairment, diseases associated with undesired oxidation, age-associated pathological processes and progeria, cardiovascular diseases such as atherosclerosis, atrial fibrillation, dyslipidemia, hypercholesterolemia, hyperlipidemia, and hypertriglyceridemia, inflammation or inflammatory processes, or epilepsy, epileptic seizures and convulsions.

Double oxidation of the cyclic nonaketide dihydromonacolin L to monacolin J by a single cytochrome P450 monooxygenase, LovA

Lovastatin, a cyclic nonaketide from Aspergillus terreus, is a hypercholesterolemic agent and a precursor to simvastatin, a semi-synthetic cholesterol-lowering drug. The biosynthesis of the lovastatin backbone (dihydromonacolin L) and the final 2-methylbutyryl decoration have been fully characterized. However, it remains unclear how two central reactions are catalyzed, namely, introduction of the 4a,5-double bond and hydroxylation at C-8. A cytochrome P450 gene, lovA, clustered with polyketide synthase lovB, has been a prime candidate for these reactions, but inability to obtain LovA recombinant enzyme has impeded detailed biochemical analyses. The synthetic codon optimization and/or N-terminal peptide replacement of lovA allowed the lovA expression in yeast (Saccharomyces cerevisiae). Both in vivo feeding and in vitro enzyme assays showed that LovA catalyzed the conversion of dihydromonacolin L acid to monacolin L acid and monacolin J acid, two proposed pathway intermediates in the biosynthesis of lovastatin. LovA was demonstrated to catalyze the regio- and stereo-specific hydroxylation of monacolin L acid to yield monacolin J acid. These results demonstrate that LovA is the single enzyme that performs both of the two elusive oxidative reactions in the lovastatin biosynthesis.

Synthesis of deuterium-labeled simvastatin

This study describes the synthesis of deuterium-labeled simvastatin. The stable isotope-labeled compound was prepared starting from lovastatin in nine steps with 9% overall yield.