50706-57-5

Basic information

• Product Name: 4-(DIPHENYLMETHYLENE)PIPERIDINE
• Synonyms: 4-(DIPHENYLMETHYLENE)PIPERIDINE;4-(Diphenylmethylidene)piperidine;Albb-005250
• CAS NO: 50706-57-5
• Molecular Formula: C₁₈H₁₉N
• Molecular Weight: 249.35
• Product Categories: Pyrans, Piperidines &Piperazines;Pyrans, Piperidines & Piperazines
• Mol File: 50706-57-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 77-78 °C
• Boiling Point: 406°C at 760 mmHg
• Flash Point: 212.3°C
• Appearance: /
• Density: 1.053g/cm³
• Vapor Pressure: 8.42E-07mmHg at 25°C
• Refractive Index: 1.591
• PKA: 10.48±0.20(Predicted)
• CAS DataBase Reference: 4-(DIPHENYLMETHYLENE)PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DIPHENYLMETHYLENE)PIPERIDINE(50706-57-5)
• EPA Substance Registry System: 4-(DIPHENYLMETHYLENE)PIPERIDINE(50706-57-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 50706-57-5(Hazardous Substances Data)

Usage

General Description

4-(Diphenylmethylene)Piperidine, also known as benhydrylidenepiperidine, is an organic compound bearing a piperidine ring that is substituted with a diphenylmethylene moiety at position 4. It is a hallmark constituent in numerous pharmaceuticals owing to its medicinal properties and drug-likeness. It is often used as an intermediate in organic synthesis and has a critical role in medicinal chemistry. The piperidine ring is the core foundation for many natural bioactive compounds. This chemical compound is a rich source of inspiration for medicinal chemists for designing new therapeutical offerings. As a volatile crystalline solid, it needs to be stored in cool, dry, well-ventilated spaces to maintain its stability and prolong its shelf life.

InChI:InChI=1/C18H19N/c1-3-7-15(8-4-1)18(16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,19H,11-14H2

Upstream product

• 58113-28-3 N-acetyl-α,α-diphenyl-4-piperidinemethanol 
• 305794-67-6 1-t-butoxycarbonyl-4-(hydroxydiphenyl)methylpiperidine 
• 102449-34-3 4-diphenylmethylene-1-piperidinecarboxylic acid ethyl ester 
• 25519-80-6 4-(benzoyl)piperidine hydrochloride 
• 100-58-3 phenylmagnesium bromide 
• 119-61-9 benzophenone 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 
• 5570-77-4 4-chloro-1-methylpiperidine 
• 142851-03-4 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate 
• 6071-93-8 NSC 31633 
• 115-46-8 C₁₈H₂₁NO 

Downstream Products

• 111626-98-3 1-{4-[3-(4-Benzhydrylidene-piperidin-1-yl)-propoxy]-3-methoxy-phenyl}-ethanone; compound with oxalic acid 
• 137540-96-6 2-[2-(4-Benzhydrylidene-piperidin-1-yl)-ethyl]-2,5,6,7,8,9-hexahydro-[1,2,4]triazolo[4,3-a]azepin-3-one 
• 117830-21-4 1-(4-aminobutyl)-4-(diphenylmethylene)-piperidine 
• 150556-87-9 1-[2-(4-diphenylmethylene-1-piperidinyl)ethyl]piperazine 
• 150557-47-4 4-(diphenylmethylene)-1-(2-chloroethyl)piperidine 
• 93052-68-7 1-(4-(tert-butyl)phenyl)-4-(4-(diphenylmethylene)piperidin-1-yl)butan-1-ol 
• 1620773-76-3 C₂₅H₂₄N₂S 
• 1449792-46-4 N-(4-fluorobenzyl)-4-hydroxy-2-(4-(diphenylmethylidene)piperidin-1-yl)butanamide 
• 1449792-44-2 N-(4-chlorobenzyl)-4-hydroxy-2-(4-(diphenylmethylidene)piperidin-1-yl)butanamide 
• 1449792-42-0 N-(2-chlorobenzyl)-4-hydroxy-2-(4-(diphenylmethylidene)piperidin-1-yl)butanamide 
• 1449792-40-8 N-benzyl-4-hydroxy-2-(4-(diphenylmethylidene)piperidin-1-yl)butanamide 

Relevant articles and documents

Synthesis and anticancer evaluation of 6-azacyclonol-2,4,6-trimethylpyridin-3-ol derivatives: M3 muscarinic acetylcholine receptor-mediated anticancer activity of a cyclohexyl derivative in androgen-refractory prostate cancer

We recently reported 2,4,5-trimethylpyridin-3-ol with C(6)-azacyclonol, whose code name is BJ-1207, showing a promising anticancer activity by inhibiting NOX-derived ROS in A549 human lung cancer cells. The present study was focused on structural modification of the azacyclonol moiety of BJ-1207 to find a compound with better anticancer activity. Ten new compounds (3A–3J) were prepared and evaluated their inhibitory actions against proliferation of eighteen cancer cell lines as a primary screening. Among the ten derivatives of BJ-1207, the effects of compounds 3A and 3J on DU145 and PC-3, androgen-refractory cancer cell lines (ARPC), were greater than the parent compound, and compound 3A showed better activity than 3J. Antitumor activity of compound 3A was also observed in DU145-xenografted chorioallantoic membrane (CAM) tumor model. In addition, the ligand-based target prediction and molecular docking study using DeepZema server showed compound 3A was a ligand to M3 muscarinic acetylcholine receptor (M3R) which is overexpressed in ARPC. Carbachol, a muscarinic receptor agonist, concentration dependently increased proliferation of DU145 in the absence of serum, and it also activated NADPH oxidase (NOX). The carbachol-induced proliferation and NOX activity was significantly blocked by compounds 3A in a concentration-dependent manner. This finding might become a new milestone in the development of pyridinol-based anti-cancer agents against ARPC.

METHODS AND COMPOSITIONS FOR TREATING INFECTION

Provided herein are compositions and methods for treating or preventing infection.

Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus

Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.