51744-85-5

Basic information

• Product Name: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol
• Synonyms: 4-quinolinemethanol, alpha-[(2S)-2-piperidinyl]-2,8-bis(trifluoromethyl)-, (alphaS)-
• CAS NO: 51744-85-5
• Molecular Formula: C₁₇H₁₆F₆N₂O
• Molecular Weight: 378.3122
• Mol File: 51744-85-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 415.7°C at 760 mmHg
• Flash Point: 205.2°C
• Density: 1.383g/cm³
• Vapor Pressure: 1.18E-07mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol(51744-85-5)
• EPA Substance Registry System: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol(51744-85-5)

Safety Data

• Hazardous Substances Data: 51744-85-5(Hazardous Substances Data)

Usage

Description

(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol is a complex organic compound characterized by its quinoline and piperidine moieties. It features two trifluoromethyl groups attached to the quinoline ring, which may contribute to its biological activity. This molecule has potential applications in various fields due to its unique structural features and properties.

Uses

Used in Pharmaceutical Industry:
(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol is used as a potential therapeutic agent for various diseases. Its unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Antimalarial Applications:
As a derivative of Mefloquine, a well-known quinoline methanol antimalarial agent, (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol may be used as an antimalarial drug. It could potentially exhibit activity against Plasmodium parasites, which cause malaria, and provide a new treatment option for this life-threatening disease.
Used in Drug Delivery Systems:
Similar to gallotannin, (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2S)-piperidin-2-yl]methanol may also benefit from novel drug delivery systems to enhance its bioavailability and therapeutic outcomes. By employing carriers such as organic and metallic nanoparticles, the compound's delivery, efficacy, and overall performance in treating various conditions could be improved.

Upstream product

• 35853-45-3 (2,8-bis-trifluoromethyl)-4-bromoquinoline 
• 57120-56-6 2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde 
• 35853-55-5 [2,8-bis(trifluoromethyl)-4-quinolinyl]-2-pyridinylmethanone 

Relevant articles and documents

The antimalarial drug mefloquine enhances TP53 premature termination codon readthrough by aminoglycoside G418

Nonsense mutations constitute ~10% of TP53 mutations in cancer. They introduce a premature termination codon that gives rise to truncated p53 protein with impaired function. The aminoglycoside G418 can induce TP53 premature termination codon readthrough and thus increase cellular levels of full-length protein. Small molecule phthalimide derivatives that can enhance the readthrough activity of G418 have also been described. To determine whether readthrough enhancers exist among drugs that are already approved for use in humans, we tested seven antimalarial drugs for readthrough of the common R213X TP53 nonsense mutation in HDQ-P1 breast cancer cells. Mefloquine induced no TP53 readthrough activity as a single agent but it strongly potentiated readthrough by G418. The two enantiomers composing pharmaceutical mefloquine potentiated readthrough to similar levels in HDQ-P1 cells and also in SW900, NCI-H1688 and HCC1937 cancer cells with different TP53 nonsense mutations. Exposure to G418 and mefloquine increased p53 phosphorylation at Ser15 and P21 transcript levels following DNA damage, indicating p53 produced via readthrough was functional. Mefloquine does not appear to enhance readthrough via lysosomotropic effects as it did not significantly affect lysosomal pH, the cellular levels of G418 or its distribution in organellar or cytosolic fractions. The availability of a readthrough enhancer that is already approved for use in humans should facilitate study of the therapeutic potential of TP53 readthrough in preclinical cancer models.

A stereospecific synthesis and unambiguous assignment of the absolute configuration of (-)-erythro-Mefloquine hydrochloride

(-)-erythro-Mefloquine hydrochloride was synthesized stereospecifically from commercially available (S)-(-)-1-Boc-2-piperidinecarboxylic acid in four steps without disturbing the chiral center, and the absolute configuration of (-)-erythro-mefloquine hydrochloride was unambiguously determined as (11R,12S). (11S,12R)-(+)-erythro-Mefloquine hydrochloride was synthesized utilizing [(S,S)-TsDpen]Ru(p-cymene)Cl complexes-catalyzed enantioselective transfer hydrogenation of pyridyl ketone 7 as the key step, and the sense of asymmetric induction of 2-pyridyl ketone 7 is opposite to that of normal ketones in the transfer hydrogenation. Our results confirm the correctness of the determination of the absolute configuration by three physical chemistry methods, and, unbelievably, the erroneous assignments by all previous five asymmetric syntheses. Copyright