51744-84-4

Usage

Uses

Used in Pharmaceutical Development:
(R)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol is used as a potential drug candidate for the development of new pharmaceuticals. Its structural features, including the piperidine ring for hydrogen bonding and the quinoline ring with trifluoromethyl groups for hydrophobic and aromatic interactions, make it suitable for engaging with biological targets.
Used in Research and Development:
(R)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol is also used as a research tool for studying biological systems. Its ability to interact with various biological molecules through different bonding mechanisms allows scientists to investigate its potential applications and mechanisms of action in the context of various diseases and conditions.
Used in Drug Design and Optimization:
In the field of medicinal chemistry, (R)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol is used as a starting point for designing and optimizing new drugs. Its unique structural features can be further modified to enhance its pharmacological properties, such as potency, selectivity, and bioavailability, making it a valuable asset in the drug discovery process.
Used in Drug Delivery Systems:
(R)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol can be employed in the development of drug delivery systems, where its interactions with biological targets can be leveraged to improve the delivery, bioavailability, and therapeutic outcomes of various pharmaceuticals. This application can be particularly useful in enhancing the efficacy of drugs with poor solubility or limited bioavailability.

Upstream product

• 866619-92-3 (R)-tert-butyl 2-((R)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidine-1-carboxylate 
• 35853-45-3 (2,8-bis-trifluoromethyl)-4-bromoquinoline 
• 57120-56-6 2,8-bis(trifluoromethyl)-4-quinoline carboxaldehyde 
• 35853-41-9 2,8-bis(trifluoromethyl)quinolin-4-ol 
• 821-41-0 5-Hexen-1-ol 
• 52898-33-6 N-(5-hexenyl)phthalimide 
• 6097-08-1 2-(hex-5-yn-1-yl)isoindole-1,3-dione 

Relevant academic research and scientific papers

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.

Practical asymmetric synthesis of (+)-erythro mefloquine hydrochloride

A highly enantioselective and cost efficient process for the synthesis of (+)-erythro mefloquine has been developed. The key step is an enantioselective reduction of pyridyl ketone KI using transfer hydrogenation with formic acid as the hydrogen source. T

Asymmetric Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride

The asymmetric (er > 99:1) total synthesis of (+)-anti- and (-)-syn-mefloquine hydrochloride from a common intermediate is described. The Sharpless asymmetric dihydroxylation is the key asymmetric transformation used in the synthesis of this intermediate. It is carried out on an olefin that is accessed in three steps from commercially available materials, making the overall synthetic sequence very concise. The common diol intermediate derived from the Sharpless asymmetric dihydroxylation is converted into either a trans- or cis-epoxide, and these are subsequently converted to (+)-anti- and (-)-syn-mefloquine, respectively. X-ray crystallographic analysis of derivatives of (+)-anti- and (-)-syn-mefloquine is used to lay to rest a 40 year argument regarding the absolute stereochemistry of the mefloquines. A formal asymmetric (er > 99:1) synthesis of (+)-anti-mefloquine hydrochloride is also presented that uses a Sharpless asymmetric epoxidation as a key step.

A Concise and Highly Enantioselective Total Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride: Definitive Absolute Stereochemical Assignment of the Mefloquines

A concise asymmetric (>99:1 e.r.) total synthesis of (+)-anti- and (-)-syn-mefloquine hydrochloride from a common intermediate is described. The key asymmetric transformation is a Sharpless dihydroxylation of an olefin that is accessed in three steps from commercially available materials. The Sharpless-derived diol is converted into either a trans or cis epoxide, and these are subsequently converted into (+)-anti- and (-)-syn-mefloquine, respectively. The synthetic (+)-anti- and (-)-syn-mefloquine samples were derivatized with (S)-(+)-mandelic acid tert-butyldimethylsilyl ether, and a crystal structure of each derivative was obtained. These are the first X-ray structures for mefloquine derivatives that were obtained by coupling to a known chiral, nonracemic compound, and provide definitive confirmation of the absolute stereochemistry of (+)-anti- as well as (-)-syn-mefloquine.

Concise synthesis and antimalarial activity of all four mefloquine stereoisomers using a highly enantioselective catalytic borylative alkene isomerization

The pluses and minuses of mefloquine: A highly enantioselective catalytic borylative isomerization/aldehyde allylboration method for the stereoselective synthesis of the antimalarial drug mefloquine was optimized, thus leading to an efficient synthesis of all four mefloquine stereoisomers and analogues (see scheme). The absolute configuration of these potent compounds was determined for the first time by using chemical synthesis. Copyright