19841-73-7

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(Diphenylmethyl)piperidine is used as a synthetic intermediate for the development of complex pharmaceutical compounds. Its role in the synthesis process is crucial for creating biologically active molecules with potential therapeutic applications.
Used in the Synthesis of N-type Calcium Channel Blockers:
In the field of cardiovascular medicine, 4-(diphenylmethyl)piperidine is utilized as a key component in the synthesis of diphenyl lactam derivatives. These derivatives function as N-type calcium channel blockers, which are essential in managing various heart conditions and related disorders by regulating the flow of calcium ions through the cell membranes of cardiac muscle cells.
Used in Organic Chemistry Research:
Due to its unique chemical properties and solubility characteristics, 4-(diphenylmethyl)piperidine can be employed in organic chemistry research to explore new reactions, mechanisms, and the development of novel synthetic methods. Its versatility in solubility allows for its use in a wide range of experimental setups and conditions.
Used in Drug Delivery Systems:
Similar to gallotannin, 4-(diphenylmethyl)piperidine could potentially be incorporated into drug delivery systems to enhance the bioavailability and therapeutic outcomes of the synthesized pharmaceutical compounds. Its compatibility with various organic solvents and acids may facilitate the design of innovative drug delivery platforms, such as nanoparticles or other carriers, to improve the efficacy of the resulting medications.

InChI:InChI=1/C18H21N/c1-3-7-15(8-4-1)18(16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,17-19H,11-14H2

Upstream product

• 3678-72-6 diphenyl-4-pyridylmethane 
• 861014-89-3 3-benzhydryl-1,5-dibromo-pentane 
• 115-46-8 C₁₈H₂₁NO 
• 50706-57-5 4-(diphenylmethylene)piperidine 
• 626-61-9 4-Chloropyridine 
• 305794-67-6 1-t-butoxycarbonyl-4-(hydroxydiphenyl)methylpiperidine 
• 86-29-3 Diphenylacetonitrile 
• 142851-03-4 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate 
• 1126-09-6 4-carbethoxypiperidine 
• 164650-64-0 N-(tert-butoxycarbonyl)-4-[hydroxy(diphenyl)methyl]piperidine 

Downstream Products

• 102654-88-6 N-(4-benzhydryl-piperidinomethyl)-succinimide 
• 354563-90-9 (4-Benzhydrylpiperidin-1-yl)-((2S)-1-ethylpiperidin-2-yl)-methanone Hydrochloride 
• 94916-53-7 3-(4-diphenylmethylpiperidin-1-yl)propionitrile 
• 60284-70-0 1-[4-[3-[4-(Diphenylmethyl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone oxalate 
• 60284-64-2 4-(α-Phenyl)benzylpiperidine-1-carboxanilide 
• 64358-97-0 1-[4-(dimethylamino)benzoyl]-4-(diphenylmethyl)piperidine 
• 64358-93-6 1-[(4-nitrophenyl)methyl]-4-(diphenylmethyl)piperidine 

Relevant academic research and scientific papers

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.

HETEROCYCLIC COMPOUNDS

The invention provides new heterocyclic compounds having the general formula (I) wherein A, L, Q, U, V, W, X, Z, m, n, and R1 to R4 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.

NEW HETEROCYCLIC COMPOUNDS

The invention provides new heterocyclic compounds having the general formula (IA) wherein A, L, X, Y, m, n, R1 and R2 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.

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.

PIPERIDINE DERIVATIVES USEFUL AS CCR5 ANTAGONISTS

Pharmaceutical compositions for the treatment of HIV are provided comprising compounds of formula (II) or a pharmaceutically acceptable salt or isomer thereof, in combination with specified antiviral agents.

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.

Ketanserin analogues: The effect of structural modification on 5-HT2 serotonin receptor binding

Ketanserin (1) is a fairly selective 5-HT2 antagonist that binds both at 5-HT2A and 5-HT2C receptors. A previous structure-affinity relationship study revealed that the structure of the piperidine-containing ketanserin molecule could be rather severely abbreviated with little effect on 5-HT2A affinity. The present investigation explores several inconsistencies identified in the earlier study and suggests that multiple modes of binding may be possible for ketanserin analogues. Perhaps the nature of the benzylic substituent is the most significant determinant of the manner in which these agents bind at 5- HT2A receptors, and it is possible that certain orientations may avail themselves of an auxiliary binding site. Depending upon the length of the piperidine N-alkyl chain, variation of the benzylic substituent from a carbonyl, to an alcohol, to a methylene group has a nonparallel influence on binding, and this may be further affected by the presence of a second ring nitrogen atom. The results of the present investigation provide evidence that although the structure of ketanserin can be abbreviated, and even modified by conversion of the piperidine ring to a piperazine, the resultant analogues may bind in more than one orientation at the receptors. A key structural feature that may play a prominent role in anchoring or orienting these compounds at 5-HT2A receptors is the benzylic carbonyl group.

Aryl(alkyland alkylene)-N-((phenoxy and phenylthio)alkyl) aminoheterocyclics as cardiovascular, anthihistaminic, antisecretory and antiallergy agents

A method of treating cardiac dysfunction, the effects of histamine, and gastric secretion excesses with aryl(alkyl and alkylene)-N-[(phenoxy and phenythio)alkyl]aminoheterocyclics corresponding to the formula: STR1 wherein Ar is phenyl or substituted phenyl; R is phenyl, substituted phenyl, pyridinyl or cycloalkyl; A is hydrogen, hydroxy, cyano, amido and amino; Q is --CH2 --, --CH--, or --CHOH--; d and n are zero or one and the dotted lines form double bonds consistent with the valence of carbon; p is zero, one or two; m is one to six inclusive; B is oxygen, nitrogen, sulfur, sulfinyl or sulfonyl; z is zero or one; l is zero or one; W is hydrogen, loweralkyl, halo, nitro, loweralkoxy or hydroxy; X is hydrogen, loweralkyl, halogen, loweralkoxy or hydroxy; Y is --CH(OH)CH2 OH, --CH(OH)C(O)OH, --C(O)C(O)OH, --C(O)CH2 OH,--C(O)C(O)OCH3, --C(O)C(O)OC2 H5, --CH2 C(O)OC2 H5, --CH(OH)C(O)OCH3, --CH(OH)C(O)OC2 H5 or --C(O)CH2 OC(O)CH3 ; and the pharmaceutically acceptable salts thereof; in addition to the above methods of treatment, compounds wherein (B)z is oxygen are useful in a method of treating Gell and Coombs type 1 allergic responses in mammals.