43171-49-9

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 83, p. 429, 1961 DOI: 10.1021/ja01463a042

InChI:InChI=1/C13H10Cl2O/c14-10-7-5-9(6-8-10)13(16)11-3-1-2-4-12(11)15/h1-8,13,16H

Upstream product

• 36692-27-0 2-chlorophenylmagnesium bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 106-39-8 bromochlorobenzene 
• 89-98-5 2-chloro-benzaldehyde 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 85-29-0 2,4'-dichlorobenzophenone 
• 90155-46-7 1R,2R-trans-diphenyl-1,2-ethanediamine 

Downstream Products

• 52094-02-7 o-Chlorophenyl-1-p'-chlorophenylmethane 
• 791118-68-8 1-benzhydryl-3-[(2-chlorophenyl)-(4-chlorophenyl)-methoxy]-azetidine 
• 1404055-03-3 3-(((2-chlorophenyl)(4-chlorophenyl)methoxy)-carbonyl)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]octane 2,2,2-trifluoroacetate 
• 1404055-01-1 (2-chlorophenyl)(4-chlorophenyl)methyl quinuclidine-3-carboxylate 
• 1404054-64-3 (3R)-3-(((2-chlorophenyl)(4-chlorophenyl)methoxy)-carbonylamino)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo-[2.2.2]octane chloride 
• 1404054-63-2 (2-chlorophenyl)(4-chlorophenyl)methyl (R)-quinuclidin-3-ylcarbamate 
• 61023-86-7 2,4'-dichlorodiphenyl bromomethane 
• 791119-48-7 1-benzyl-4-(2,4'-dichlorobenzhydryloxy)piperidine 
• 508211-40-3 methyl 2-[(2-chlorophenyl)(4'-chlorophenyl)methoxy]-5-nitrobenzoate 
• 93535-56-9 Methoxy-(2-chlor-phenyl)-(4-chlor-phenyl)-methan 
• 96581-30-5 1,2-Bis-(2-chlor-phenyl)-1,2-bis-(4-chlor-phenyl)-ethan 
• 34113-46-7 1-(2-chlorophenyl)-1-(4-chlorophenyl)acetic acid 
• 97027-84-4 (2-chlorophenyl)(4-chlorophenyl)methyl chloride 
• 1026410-64-9 [3(2,4'-dichlorobenzhydryloxy)azetidin-1-yl]piperidin-1-ylmethanone 

Relevant academic research and scientific papers

Substituent Position-Controlled Stereoselectivity in Enzymatic Reduction of Diaryl- and Aryl(heteroaryl)methanones

We report here the discovery of a novel ketoreductase (KRED), named KmCR2, with a broad substrate spectrum on bioreduction of sterically bulky diaryl- and aryl(heteroaryl)methanones. The position of the substituent on aromatic rings (meta versus para or ortho) was revealed to control the stereospecificity of KmCR2. The stereoselective preparation of both enantiomers of diaryl- or aryl(heteroaryl)methanols using strategically engineered substrates with a traceless directing group (bromo group) showcased the potential application of this substrate-controlled bioreduction reaction. The combined use of substrate engineering and protein engineering, was demonstrated to be a useful strategy in efficiently improving stereoselectivity or switching stereopreference of enzymatic processes. (Figure presented.).

Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats.

Synthesis and anticonvulsant activity of some cinnamylpiperazine derivatives

A series of cinnamylpiperazine derivatives was synthesized using different benzophenone as starting material. The structures of the compounds were proved by their IR, 1H-NMR spectroscopic data and mass spectra data. The anticonvulsant activities of these compounds were evaluated with maximal electroshock (MES) test and rotarod test with intraperitoneal injection on KunMing mice. Among all the flunarizine analogues, no one exhibited better anticonvulsant activity than flunarizine. Flunarizine (4i) exhibited anticonvulsant activity with ED50 of 38.1 mg/kg, TD50 of 164.3 mg/kg and PI of 4.3 through administration intraperitoneal, and with ED50 of 56.8 mg/kg, TD50 of 456.3 mg/kg and PI of 8.0 through oral administration.

Convenient synthesis of structurally novel 1,3-disubstituted azetidine derivatives

A convenient synthesis of structurally novel 1,3-disubstituted azetidine derivatives is described. The approach involves condensation of an azetidine building block with sulfonylated carbamic acid methyl ester, subsequently followed by quenching the imidoyl chloride with amines. Different derivatives were prepared by substituting benzhydrol as well as benzenesulfonamide as part of the core structure. Copyright Taylor & Francis Group, LLC.

Design, synthesis and biological evaluation of piperazine analogues as CB1 cannabinoid receptor ligands

After the CB1 receptor antagonist SR141716 (rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. Several series of urea, carbamate, amide, sulfonamide and oxalamide derivatives based on 1-benzhydrylpiperazine scaffold were synthesized and tested for CB1 receptor binding affinity. The SAR studies to optimize the CB1 binding affinity led to the potent urea derivatives. After the additional SAR studies to optimize the substituents of diphenyl rings, the combination of 2-chlorophenyl and 4-chlorophenyl turned out to be the most potent scaffold. The CB2 binding affinity assay as well as functional assay was also conducted on these compounds. Herein we wish to introduce several novel CB1 antagonists with IC50 values less than 100 nM for the CB1 receptor binding.

BENZENE DERIVATIVES,PROCESS FOR PREPARING THE SAME AND USE THEREOF

Novel benzene derivatives represented by the formula (I) : wherein R1, R4 and R6 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group, R2 represents a hydrocarbon group or a heterocyclic group, R3 represents a hydrocarbon group, NR7'R7 or OR8 (wherein R7' represents a hydrogen atom or a hydrocarbon group, R7 represents a non-aromatic group, or R7' and R7 may form a ring with the adjacent nitrogen atom, and R8 represents a hydrocarbon group or a heterocyclic group), R5 represents a hydrocarbon group or a heterocyclic group (except for a quinolyl group), R5' represents a hydrogen atom, or a hydrocarbon group, or R5 and R5' may form a ring with the adjacent nitrogen atom, and R5" represents a hydrogen atom or a hydrocarbon group, which have vanilloid receptor agonist activity and are useful as a drug such as an analgesic and an agent for preventing and/or treating urinary frequency and/or urinary incontinence.

AZETIDINECARBOXAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CB1 RECEPTOR MEDIATED DISORDERS

Compounds of formula (I) and their use in therapy, particularly for the treatment of a disorder mediated by CB1 receptors such as obesity: Formuila (I) wherein: R1 and R2 are independently selected from aryl; and R3 is hydrogen or alkyl; or a pharmaceutically acceptable salt or prodrug thereof, wherein at least one of R1 and R2 has a non-hydrogen substituent in the ortho-position(s) thereof relative to the point of attachment to the [-CH-0-] group.

AZETIDINECARBOXAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CB1 RECEPTOR MEDIATED DISORDRS

Compounds of formula (I) and their use in therapy, particularly for the treatment of a disorder mediated by CB1 receptors, such as obesity, wherein: R1 is aryl or heteroaryl; R2 is alkyl, aryl or heteroaryl; R3 is alkyl, aryl, heteroaryl, NR9R10, OR 15, or NR16C(O)R17;Y is C=O, C=S, SO2, or (CR7R8)p; m = 1 or 2; n = 1 or 2; and p=1,2,3 or 4, R7 to R17 being as defined in the specification; wherein if -Y-R3 is -C(O)NH(alkyl) then: R1 and/or R2 is selected from heteroary1; and/or m and/or n is 2; and/or R11 and/or R12 is lower alkyl, or a pharmaceutically acceptable salt or prodrug thereof.

Insecticidal N-heterocyclylalkyl-or N-[(polycyclyl)alkyl]-N′substituted piperazines

Compounds of the following structure are disclosed as effective insecticides: in which: A and B are independently lower alkyl; U is lower alkylidene, lower alkenylidene, or CH—Z, where Z is hydrogen, lower alkyl, lower cycloalkyl, or phenyl; R is phenyl o

Process for producing optically active benzhydrol compounds

A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: STR1 wherein R1 to R10 each represents H, OH, C1-4 alkyl, C1-4 alkoxy, C1-4 alkanoyl, etc., R2 and R3, and R8 and R9 may form --CH=CH--CH=CH--, or any two of R1 to R9 adjacent to each other may be bonded to thereby form --OCH2 O-- or --(CH2)3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.