148901-68-2

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl-2-propenal is used as a pharmaceutical compound for its potential therapeutic effects due to its anti-inflammatory and anti-cancer properties. It is being studied for its ability to modulate various biological pathways and target specific diseases.
It is important to handle this chemical with care and follow proper safety procedures when working with it in the laboratory to ensure the safety of researchers and the integrity of the experiments.

InChI:InChI=1/C21H16FNO/c22-16-11-9-14(10-12-16)20-17-4-1-2-6-19(17)23-21(15-7-8-15)18(20)5-3-13-24/h1-6,9-13,15H,7-8H2/b5-3+

Upstream product

• 113832-57-8 N-ethylidenecyclohexylamine 
• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 
• 7020-80-6 acetaldehyde N-tert-butylimine 
• 6898-74-4 Acetaldehyd-butylimin 
• 1403338-19-1 methyl (2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]acrylate 
• 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 
• 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 
• 391681-95-1 2-cyclopropyl-3-(3-ethoxy-1-hydroxy-2-propenyl)-4-(4-fluorophenyl)quinoline 
• 256431-72-8 (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile 

Downstream Products

• 254452-93-2 (E)-(R)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid (R)-2-hydroxy-1,2,2-triphenyl-ethyl ester 
• 254452-89-6 (E)-(S)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester 
• 254452-95-4 ethyl 5(R)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 254452-91-0 ethyl 5(S)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 222306-21-0 (E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-acrylic acid 
• 172336-32-2 (±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester 
• 562099-41-6 (S,E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-hydroxy-3-oxo-6-heptenoic acid isopropyl ester 
• 1403338-20-4 (1S)-2-hydroxy-1,2,2-triphenylethyl (4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxy-4-pentenoate 
• 1403338-25-9 ethyl (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3,5-dihydroxy-6-heptenoate, trifluoroacetate salt 
• 1403338-24-8 ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate 
• 1403338-27-1 C₂₉H₃₄FNO₃Si 
• 222306-19-6 (3S,4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxypentenoic acid 

Relevant academic research and scientific papers

Synthesis method of (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein

The invention relates to a synthesis technology of pharmaceutical chemicals and particularly relates to a synthesis technology of (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein. (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-2-ethyl acrylate is taken as a raw material, and is thoroughly reduced into allyl alcohol through hydroboron, (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein is synthesized through DMSO oxidation, reaction conditions are optimized, and the yield of the (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein reaches over 95%. The method is simple in operation step, short in reaction period and high in conversion ratio; the required equipment is simple; the method is suitable for industrial massive production; the content of the produced (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein is greater than 99%; and the technical requirements of the market on the (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein are met.

PROCESS FOR PREPARING QUINOLINE DERIVATIVE

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

PROCESS FOR PRODUCING QUINOLINE COMPOUND

By a production method of a quinoline compound represented by the formula (I), which comprises reacting quinolinecarbaldehyde represented by the formula (II) with an imine compound represented by the formula (III) and then subjecting the resulting compoun

PROCESS FOR PREPARING QUINOLYLACRYLONITRILE AND INTERMEDIATES THEREFOR

3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrite is prepared by reacting 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde with acetonitrile in the presence of a base and then adding a dehydrating to the reaction mixture to conduct

PROCESS FOR THE PREPARATION OF QUINOLYLPROPENAL

3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enal is prepared in a high yield by reducing 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrite with Raney nickel either in the presence of formic acid and 0.25 to 1 part by volume of water per part by volume of formic acid or in the presence of both an amine salt of formic acid and an organic acid.

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.