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

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

Uses

Used in Pharmaceutical Industry:
4-(Diphenylmethylene)Piperidine is used as an intermediate in organic synthesis for the development of various pharmaceuticals. Its medicinal properties and drug-likeness make it a crucial component in the creation of new drugs.
Used in Medicinal Chemistry:
4-(Diphenylmethylene)Piperidine is used as a foundational structure in the design of new therapeutic agents. The piperidine ring serves as a core for many natural bioactive compounds, providing a rich source of inspiration for medicinal chemists.
Used in Drug Development:
4-(Diphenylmethylene)Piperidine is used as a key constituent in drug development, contributing to the medicinal properties and drug-likeness of new pharmaceuticals. Its presence in numerous pharmaceuticals highlights its importance in the field of medicinal chemistry.

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

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

Downstream Products

• 117830-21-4 1-(4-aminobutyl)-4-(diphenylmethylene)-piperidine 
• 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 
• 111626-98-3 1-{4-[3-(4-Benzhydrylidene-piperidin-1-yl)-propoxy]-3-methoxy-phenyl}-ethanone; compound with oxalic acid 
• 137406-16-7 3-(4-Benzhydrylidene-piperidin-1-yl)-propionic acid ethyl ester 
• 137406-18-9 4-(4-Benzhydrylidene-piperidin-1-yl)-butyric acid ethyl ester 
• 137406-19-0 5-(4-Benzhydrylidene-piperidin-1-yl)-pentanoic acid ethyl ester 
• 688304-93-0 6-(4-Benzhydrylidene-piperidin-1-yl)-hexanoic acid methyl ester 
• 167108-56-7 (4-Benzhydrylidene-piperidin-1-yl)-acetic acid ethyl ester 
• 158399-51-0 2-cyano-7-<<3-<4-(diphenylmethylene)piperidin-1-yl>propyl>oxy>-4-oxo-4H-1-benzopyran 
• 43076-31-9 4'-fluoro-4-(4-diphenylmethylenepiperidino)butyrophenone 
• 19841-73-7 4-(Diphenylmethyl)piperidine 

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.

PROCESS FOR THE PREPARATION OF FEXOFENADINE AND OF INTERMEDIATES USED THEREIN

A new process for the preparation of fexofenadine and of related intermediates, which can be used in the preparation of fexofenadine, is provided.

METHODS AND COMPOSITIONS FOR TREATING INFECTION

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

NON-PEPTIDIC NEUROPEPTIDE Y RECEPTOR MODULATORS

The invention provides compounds that are modulators of neuropeptide Y (NPY) receptors, which can be selective inhibitors of NPY receptor Y2R. NPY receptor modulatory compounds are of the general formula Ar2-Y-Ar1-W-Ar3, wherein the variables are as defined herein. Compounds of the invention can be used for treatment of malconditions in patients wherein modulation of an NPY receptor is medically indicated, for example including drug or alcohol abuse, anxiety disorders, depression, stress-related disorders, neurological disorders, nerve degeneration, osteoporosis or bone loss, sleep/wake disorders, cardiovascular diseases, obesity, anorexia, inovulation, fertility disorders, angiogenesis, cell proliferation, learning and memory disorders, migraine and pain.

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.

Synthesis and SAR of selective small molecule neuropeptide y Y2 receptor antagonists

Highly potent and selective small molecule neuropeptide Y Y2 receptor antagonists are reported. The systematic SAR exploration of a hit molecule N-(4-ethoxyphenyl)-4-[hydroxy(diphenyl)methyl]piperidine-1-carbothioamide, identified from HTS, led to the discovery of highly potent NPY Y2 antagonists 16 (CYM 9484) and 54 (CYM 9552) with IC50 values of 19 nM and 12 nM respectively.

Characterization of tunable piperidine and piperazine carbamates as inhibitors of endocannabinoid hydrolases

Monoacylglycerol lipase (MAGL) and fatty acid amide hydrolase (FAAH) are two enzymes from the serine hydrolase superfamily that degrade the endocannabinoids 2-arachidonoylglycerol and, anandamide, respectively. We have recently discovered that, MAGL and, FAAH are both inhibited by carbamates bearing an N-piperidine/piperazine group. Piperidine/piperazine carbamates show excellent in vivo activity, raising brain endocannabinoid levels and producing CB1-dependent behavioral effects in mice, suggesting that they represent a promising class of inhibitors for studying the endogenous functions of MAGL and FAAH. Herein, we disclose a full account of the syntheses, structure-activity relationships, and, inhibitory activities of piperidine/piperazine carbamates against members of the serine hydrolase family. These scaffolds can be tuned for MAGL-selective or dual MAGL-FAAH inhibition by the attachment of an, appropriately substituted bisarylcarbinol or aryloxybenzyl moiety, respectively, on the piperidine/piperazine ring. Modifications to the piperidine/piperazine ring ablated inhibitory activity, suggesting a strict requirement for a six-membered ring to maintain potency.

Treatment of CNS disorders using CNS target modulators

The invention is directed to compositions and methods useful for treating Central Nervous System (CNS) disorders. Furthermore, the invention provides compositions and methods of treating sleep disorders. More specifically, the invention is directed to the compositions and use of derivatized, histamine antagonists for the treatment of sleep disorders.

Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with new piperidine 4-alkenyl derivatives that possess unique antiviral activity. More particularly, the present invention relates to compounds useful for the treatment of HIV and AIDS. The compounds of the invention for the general Formula I: wherein: Z is Q is selected from the group consisting of: —W— is

N-[4-(Methylsulfonylamino)benzyl]thiourea analogues as vanilloid receptor antagonists: Analysis of structure-activity relationships for the 'C-Region'

We recently reported that N-(4-t-butylbenzyl)-N′-[4- (methylsulfonylamino)benzyl] thiourea (2) was a high affinity antagonist of the vanilloid receptor with a binding affinity of Ki=63 nM and an antagonism of Ki=53.9 nM in rat VR1 heterologously expressed in Chinese hamster ovary (CHO) cells (Mol. Pharmacol. 2002, 62, 947-956). In an effort to further improve binding affinity and antagonistic potency, we have modified the C-region of the lead 4-t-butylbenzyl group with diverse surrogates, such as araalkyl, alkyl, 4-alkynylbenzyl, indanyl, 3,3-diarylpropyl, 4-alkoxybenzyl, 4-substituted piperazine and piperidine. The lipophilic surrogates, arylalkyl and alkyl, conferred modest decreases in binding affinities and antagonistic potencies; the groups having heteroatoms resulted in dramatic decreases. Our findings indicate that 4-t-butylbenzyl is one of the most favorable groups for high receptor binding and potent antagonism to VR1 in this structural series.