172336-33-3

Basic information

• Product Name: [R-(R*,S*)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester
• Synonyms: [R-(R*,S*)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester;Ethyl [R-(R*,S*)]-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-hept-6-enoate;6-Heptenoic acid,7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-,ethyl ester,[3R,5(R*,S*)]-
• CAS NO: 172336-33-3
• Molecular Formula: C27H28FNO4
• Molecular Weight: 450
• Mol File: 172336-33-3.mol

Chemical Properties

• Appearance: /
• Density: 1.271
• CAS DataBase Reference: [R-(R*,S*)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [R-(R*,S*)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester(172336-33-3)
• EPA Substance Registry System: [R-(R*,S*)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester(172336-33-3)

Safety Data

• Hazardous Substances Data: 172336-33-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
[R-(R,S)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester is used as a research compound for the development of new drugs for various conditions. Its unique structure and potential pharmaceutical properties make it an interesting target for further research and exploration in the field of medicinal chemistry.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, [R-(R,S)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester is used as a structural template for designing and synthesizing novel drug candidates. Its diverse functional groups and unique arrangement provide opportunities for modification and optimization to enhance its therapeutic potential.
Used in Drug Development:
[R-(R,S)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester is used as a starting material in the synthesis of new drug molecules. Its versatile chemical structure allows for the incorporation of various functional groups and modifications, which can lead to the development of drugs with improved efficacy, selectivity, and safety profiles.
Used in Drug Discovery:
In the drug discovery process, [R-(R,S)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester is used as a screening compound to identify potential drug candidates. Its unique structure and properties can be assessed for their ability to interact with biological targets, providing insights into its potential therapeutic applications.
Used in Biochemical Research:
[R-(R,S)]-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid ethyl ester is used as a tool compound in biochemical research to study the mechanisms of action and interactions with various biological systems. Its unique structural features can provide valuable information on the molecular basis of its potential therapeutic effects and help guide the development of more effective drugs.

Upstream product

• 64-17-5 ethanol 
• 147526-32-7 pitavastatin 
• 254452-90-9 (E)-(S)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid methyl ester 
• 254452-94-3 (E)-(R)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid methyl ester 
• 256431-72-8 (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile 
• 148901-68-2 (E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-propenal 
• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 
• 254452-91-0 ethyl 5(S)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 254452-95-4 ethyl 5(R)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 477950-34-8 ethyl (E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-3,5-dihydroxyhept-6-enoate 
• 121660-11-5 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline 
• 141-97-9 ethyl acetoacetate 
• 32249-35-7 methyl 3-cyclopropyl-3-oxopropanoate 
• 3800-06-4 2-amino-4'-fluorobenzophenone 

Downstream Products

• 147511-69-1 (E)-(3R,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 147511-69-1 (E)-(3S,5S)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 167073-18-9 (E)7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-(3S,5R)-dihydroxyhept-6-enic acid ethyl ester 
• 380848-32-8 (E)7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-(3R,5R)-dihydroxyhept-6-enic acid ethyl ester 
• 380848-30-6 (E)7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-(3S,5S)-dihydroxyhept-6-enic acid ethyl ester 
• 167073-19-0 (E)-(3R,5S)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester 
• 254452-86-3 (E)-(3S,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 

Relevant articles and documents

METHOD FOR PRODUCING PITAVASTATIN CALCIUM

Production of pitavastatin calcium safely on an industrial scale with a high yield and high selectivity at low cost. A method of producing pitavastatin calcium including step (i) for acetalizing a compound represented by the formula (1) to give a compound represented by the formula (3), step (ii) for reacting a compound represented by the formula (3) with an acid to give a compound represented by the formula (4), and step (iii) for hydrolyzing a compound represented by the formula (4) and reacting same with a calcium compound.

Virtual screening and experimental validation identify novel modulators of nuclear receptor RXRα from Drugbank database

Retinoid X receptor alpha (RXRα), an important ligand-dependent transcription factor, plays a critical role in the development of various cancers and metabolic and neurodegenerative diseases. Therefore, RXRα represents one of the most important targets in modern drug discovery. In this study, Drugbank 2.0 with 1280 old drugs were virtually screened by Glide according to the crystal structure of ligand-binding domain (LBP) of RXRα. 15 compounds selected were tested for their binding and transcriptional activity toward RXRα by Biacore and reporter gene assay, respectively. The identified new scafford ligand of RXRα, Pitavastatin (1), was chemically optimized. Our results demonstrated that statin compounds Pitavastatin (1) and Fluvastatin (4) could bind to the LBP of RXRα (KD = 13.30 μM and 11.04 μM, respectively) and serve as transcriptional antagonists of RXRα. On the contrary, compound (12) (domperidone) and (13) (rosiglitazone maleate) could bind to the LBP of RXRα (KD = 8.80 μM and 15.01 μM, respectively) but serve as transcriptional agonists of RXRα.

A pitavastatin calcium bulk drug intermediate preparation method

The invention discloses a preparing method for a pitavastatin calcium bulk drug intermediate. The intermediate is (+/-) E-6-[2- cyclopropyl-4-(4-fluorophenyl)-quinoline-3-phenyl vinyl]-4-hydroxy-3,4,5,6-tetralin-valerolactone. The method comprises the ste

PROCESS FOR PREPARING QUINOLINE DERIVATIVE

The present invention relates to a novel process for preparing Pitavastatin calcium salt of formula (I).

Process for producing (3R,5S)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin- 3-yl]-3, 5-dihydroxyhept-6-enic acid esters

A process for producing a compound represented by the following formula (IV): (wherein R denotes a hydrogen atom, an alkyl group, or an aryl group), comprising reducing a compound selected from the group consisting of: a compound represented by the following formula (I): (wherein R is as defined in the formula); a compound represented by the following formula (II): (wherein R is as defined in the formula); and a compound represented by the following formula (III): (wherein R is as defined in the formula), by reacting the compound with a cell of a microorganism and/or a cell preparation thereof capable of stereo-selectively reducing a keto group.

METHOD FOR PREPARING 7-QUINOLINYL-3,5-DIHYDROXYHEPT-6-ENOATE

A method for preparing a 7-quinolynyl-3,5-dihydroxyhept-6-enoate useful as an intermediate for pharmaceuticals, in high yield and in high purity, is presented. It is a method for preparing a 7-quinolinyl-3,5-dihydroxyhept-6-enoate represented by the formu

Process for the manufacture of organic compounds

The invention relates to a process for the manufacture of a compound of formula or a salt, especially a pharmaceutically acceptable salt with a base, thereof or a lactone thereof wherein the element represents —CH2—CH2— or —CH═CH— an

Process for the manufacture of organic compounds

A method for preparing an alkali metal salt comprising: (a) condensing a disilyloxydiene with an aldehyde in the presence of a titanium (IV) catalyst in an inert solvent to form a 5(S)-hydroxy-3-ketoester; (b) reducing the 5(S)-hydroxy-3-ketoester to a 3(

Synthesis and biological evaluations of quinoline-based HMG-CoA reductase inhibitors

A series of quinoline-based 3,5-dihydroxyheptenoic acid derivatives were synthesized from quinolinecarboxylic acid esters by homologation, aldol condensation with ethyl acetoacetate dianion, and reduction of 3-hydroxyketone to evaluate their ability to inhibit the enzyme HMG-CoA reductase in vitro. In agreement with previous literature, a strict structural requirement exists on the external ring, and 4-fluorophenyl is the most active in this system. For the central ring, substitution on positions 6, 7, and 8 of the central quinoline nucleus moderately affected the potency, whereas the alkyl side chain on the 2-position had a more pronounced influence on activity. Among the derivatives, NK-104 (pitavastatin calcium), which has a cyclopropyl group as the alkyl side chain, showed the greatest potency. We found that further modulation and improvement in potency at inhibiting HMG-CoA reductase was obtained by having the optimal substituents flanking the desmethylmevalonic acid portion, that is, 4-fluorophenyl and cyclopropyl, instead of the usual isopropyl group.

Enantioselective addition of diketene to aldehydes promoted by chiral Schiff base-titanium alkoxide complex. Application to asymmetric synthesis of potential inhibitors of HMG coenzyme reductase

Highly enantioselective addition of diketene to aldehydes was achieved by using novel Schiff base-titanium alkoxide complexes. Up to 92% ee of 5-hydroxy-3-oxoesters was obtained. This procedure provides an efficient method for the asymmetric synthesis of potential inhibitors of HMG coenzyme reductase.