634464-86-1

Usage

Chemical structure

Piperidine derivative with a hydroxy group and a BOC protecting group attached to the nitrogen atom, and a trifluoromethyl group on the phenyl ring.

Type of compound

Fluorinated organic molecule

Functional groups

a. Hydroxy group
b. BOC protecting group
c. Trifluoromethyl group

Applications

a. Intermediates in organic synthesis
b. Pharmaceutical research
c. Medicinal chemistry
d. Development of new drugs and biologically active molecules

Properties conferred by the trifluoromethyl group

a. Increased lipophilicity
b. Metabolic stability

Upstream product

• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 1683-49-4 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1191240-74-0 tert-butyl 4-(2-pyrrolidin-1-ylethoxy)-4-(3-trifluoromethyl-phenyl)-piperidine-1-carboxylate 
• 2249-28-7 4-(3-trifluoromethylphenyl)-4-hydroxy piperidine 

Relevant academic research and scientific papers

Structure-Based Design and Synthesis of Piperidinol-Containing Molecules as New Mycobacterium abscessus Inhibitors

Non-tuberculous mycobacterium (NTM) infections, such as those caused by Mycobacterium abscessus, are increasing globally. Due to their intrinsic drug resistance, M. abscessus pulmonary infections are often difficult to cure using standard chemotherapy. We previously demonstrated that a piperidinol derivative, named PIPD1, is an efficient molecule both against M. abscessus and Mycobacterium tuberculosis, the agent of tuberculosis, by targeting the mycolic acid transporter MmpL3. These results prompted us to design and synthesize a series of piperidinol derivatives and to determine the biological activity against M. abscessus. Structure-activity relationship (SAR) studies pointed toward specific sites on the scaffold that can tolerate slight modifications. Overall, these results identified FMD-88 as a new promising active analogue against M. abscessus. Also, we determined the pharmacokinetics properties of PIPD1 and showed that intraperitoneal administration of this compound resulted in promising serum concentration and an elimination half-life of 3.2 hours.

Synthesis and SAR study of diphenylbutylpiperidines as cell autophagy inducers

A novel series of diphenylbutylpiperidines as autophagy inducers was described and extensive SAR studies resulted in derivatives (15d-e, 15i-j) with 10-fold greater activity than the lead compounds 1 and 2. Meanwhile, a new synthetic route to diphenylbutyl bromide (6) from bromobenzene and γ-butyrolactone was also reported here.

SUBSTITUTED SULFONAMIDE COMPOUNDS

Substituted sulfonamide compounds corresponding to formula I processes for the preparation thereof, pharmaceutical compositions containing these compounds, and the use of such substituted sulfonamide compounds in pharmaceutical compositions for the treatment and/or inhibition of pain and other conditions at least partly mediated by the bradykinin 1 receptor

Piperazinylacylpiperidine derivatives, their preparation and therapeutic use thereof

The invention relates to substituted 1-piperazinylacylpiperidine derivatives of general formula (I) in which: n is 1 or 2; p is 1 or 2; R1 represents a halogen atom; a trifluoromethyl radical; a (C1-C4)alkyl; a (C1-C4)alkoxy; a trifluoromethoxy radical; R2 represents a hydrogen atom or a halogen atom; R3 represents a hydrogen atom; a group —OR5; a group —CH2OR5; a group —NR6R7; a group —NR8COR9; a group —NR8CONR10R11; a group —CH2NR12R13; a group —CH2NR8CONR14R15; a (C1-C4)alkoxycarbonyl; a group —CONR16R17; or else R3 constitutes a double bond between the carbon atom to which it is attached and the adjacent carbon atom of the piperidine ring; R4 represents an aromatic group selected from: the said aromatic groups being unsubstituted or being mono- or disubstituted by a substituent selected independently from a halogen atom; a (C1-C4)alkyl; a (C1-C4)alkoxy; a trifluoromethyl radical; Preparation process and therapeutic application.