121659-65-2

Basic information

• Product Name: 4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline
• Synonyms: 4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline
• CAS NO: 121659-65-2
• Molecular Weight: 295.356
• Mol File: 121659-65-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline(121659-65-2)
• EPA Substance Registry System: 4-(4'-fluorophenyl)-3-hydroxymethyl-2-(1'-methylethyl)-quinoline(121659-65-2)

Safety Data

• Hazardous Substances Data: 121659-65-2(Hazardous Substances Data)

Upstream product

• 42558-54-3 Methyl 4-methyl-3-oxopentanoate 
• 7152-15-0 ethyl 4-methyl-3-oxo-pentanoate 
• 3800-06-4 2-amino-4'-fluorobenzophenone 
• 121659-64-1 Ethyl 4-(4'-fluorophenyl)-2-(1'-methylethyl)-quinolin-3-yl-carboxylate 
• 130954-89-1 methyl 4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxylate 

Downstream Products

• 121659-66-3 4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxaldehyde 
• 118312-79-1 <4α,6β(E)>-6-<2-<4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinyl>ethenyl>tetrahydro-4-hydroxy-2H-pyran-2-one 
• 118312-79-1 (4S,6S)-6-{(E)-2-[4-(4-Fluoro-phenyl)-2-isopropyl-quinolin-3-yl]-vinyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 130954-93-7 (4R,6R)-6-{2-[4-(4-Fluoro-phenyl)-2-isopropyl-quinolin-3-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one 
• 755736-58-4 (E)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 130954-90-4 methyl (E)-3-<4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinyl>-2-propenoate 
• 121659-69-6 ethyl (E)-7-<4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinyl>-5-hydroxy-3-oxo-6-heptenoate 
• 121678-81-7 (E)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester 
• 121659-68-5 (E)-3-<4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinyl>-2-propenal 

Relevant articles and documents

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.

Synthesis of 2-(4-fluorophenyl)-4-isopropyl-3-quinolinecarbaldehyde: A new route to 2,3,4-substituted quinolines

A new method for the preparation of 2,3,4-substituted quinolines has been developed and its application towards the synthesis of 2-(4-fluorophenyl)-4-isopropyl-3-quinolinecarbaldehyde, as well as other quinolines, is described.