148901-69-3

Basic information

• Product Name: Ethyl (E)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate
• Synonyms: ETHYL (E)-7-[4-(4''-FLUOROPHENYL)-2-(CYCLOPROPYL)-3-QUINOLINYL]-5-HYDROXY-3-OXO-6-HEPTENOATE;(E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl ester;Ethyl (E)-7-[2-cyclopropyl-4-(4-flurophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate;Pitavastatin 3-Oxo Ethyl Ester;Ethyl(E)-(5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)-5-hydroxy-3-oxo-3-quinolinyl]-hept-6-enoate;(E)-Ethyl 7-(2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate;6-Heptenoic acid, 7- 2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl -5-hydroxy-3-oxo-, ethyl ester, (E)-;3-Oxo Pitavastatin Ethyl Ester
• CAS NO: 148901-69-3
• Molecular Formula: C₂₇H₂₆FNO₄
• Molecular Weight: 447.5
• EINECS: 1312995-182-4
• Mol File: 148901-69-3.mol

Chemical Properties

• Boiling Point: 651.3 °C at 760 mmHg
• Flash Point: 347.7 °C
• Appearance: /
• Density: 1.268
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.30±0.46(Predicted)
• CAS DataBase Reference: Ethyl (E)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (E)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate(148901-69-3)
• EPA Substance Registry System: Ethyl (E)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate(148901-69-3)

Safety Data

• Hazardous Substances Data: 148901-69-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (E)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate is used as an impurity in the production of Pitavastatin (P531000), a competitive inhibitor of HMG-CoA reductase and an antilipemic agent. Its presence in Pitavastatin is significant due to the role it plays in the overall efficacy and safety profile of the drug. The compound is important for quality control and regulatory compliance in the pharmaceutical industry, as it must be monitored and controlled to ensure the safety and effectiveness of Pitavastatin as a medication for treating high cholesterol and related conditions.

Upstream product

• 166803-31-2 (E)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dioxo-hept-6-enoic acid ethyl ester 
• 391681-95-1 2-cyclopropyl-3-(3-ethoxy-1-hydroxy-2-propenyl)-4-(4-fluorophenyl)quinoline 
• 121660-18-2 [2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinolin-3-yl]-methanol 
• 121660-43-3 2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinoline-3-carbaldehyde 
• 121659-86-7 methyl 4-(4'-fluorophenyl)-2-cyclopropylquinoline-3-carboxylate 
• 256431-72-8 (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile 
• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 
• 121660-11-5 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline 
• 32249-35-7 methyl 3-cyclopropyl-3-oxopropanoate 
• 3800-06-4 2-amino-4'-fluorobenzophenone 
• 141-97-9 ethyl acetoacetate 
• 148901-68-2 (E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-propenal 

Downstream Products

• 166803-31-2 (E)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dioxo-hept-6-enoic acid ethyl ester 
• 172336-32-2 (±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester 
• 147526-32-7 pitavastatin 
• 254452-86-3 (E)-(3S,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 172336-32-2 ethyl (E)-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]hept-6-enoate 

Relevant articles and documents

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 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.

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.

First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104

First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104 are reported. A pair of syn diol isomers (NK-104 and its enantiomer) was obtained efficiently by diastereomeric resolution. The synthesis of a pair of anti diol isomers (3-epimer and 5-epimer) was accomplished effectively by the asymmetric aldol reaction followed by anti stereoselective reduction as key steps. Their purity determinations were effected by chiral HPLC analysis.