3308-94-9

Usage

Chemical Properties

clear colourless to faint yellow oily liquid

InChI:InChI=1/C12H14ClFO2/c13-7-1-6-12(8-15-9-16-12)10-2-4-11(14)5-3-10/h2-5H,1,6-9H2

Upstream product

• 107-21-1 ethylene glycol 
• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 
• 462-06-6 fluorobenzene 

Downstream Products

• 55846-41-8 1-(3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl)piperazine 
• 82236-09-7 4-amino-1-<3-(4-fluorobenzoyl)propyl>pyridinium chloride ethylene acetal 
• 65053-27-2 4-(2-aminoanilino)-1-<3-(4-fluorobenzoyl)propyl>pyridinium chloride ethylene acetal 
• 801-12-7 1-(4-fluoro-phenyl)-4-(4-pyrimidin-2-yl-piperazin-1-yl)-butan-1-one 
• 161331-20-0 4-<(4-phenylpyridazinyl)piperazin-1-yl>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane 
• 59921-73-2 4-Aminobutyrophenon 
• 153208-89-0 4-Benzyl-1-(4-p-fluorophenyl-4,4-ethylendioxy)butylpiperidine 
• 214748-88-6 4-Benzyl-1-{3-[2-(4-fluoro-phenyl)-[1,3]dioxolan-2-yl]-propyl}-2-methyl-piperazine 
• 56660-98-1 1-<4-(4-fluorophenyl)-4,4-(ethylenedioxy)butyl>-4-piperidinone 
• 219563-58-3 1-methyl-8-<3-(4-fluorophenyl)-3,3-(ethylenedioxy)butyl>-1,3,8-triazaspiro<4.5>decan-4-one 

Relevant academic research and scientific papers

The synthesis of ω-(2-aryl-1,3-dioxolan-2-yl)alkyl purine derivatives and their activity towards HIV reverse transcriptase

Novel derivatives of 6-substituted purines were synthesized by alkylation of 6-substituted purines with various 2-(chloroalkyl)-2-aryl-1,3-dioxolanes and related compounds. Their inhibitory properties toward HIV reverse transcriptase were studied. The structure-activity relationship within the synthesized compounds was found.

Molecular hybridization of 4-azahexacyclo[5.4.1.02,6.0 3,10.05,9.08,11]dodecane-3-ol with sigma (σ) receptor ligands modulates off-target activity and subtype selectivity

A series of N-substituted 4-azahexacyclo[5.4.1.02,6.0 3,10.05,9.08,11]dodecan-3-ols incorporating the respective arylalkyl subunits from several known sigma (σ) receptor ligands were synthesized and evaluated for their affinity against σ receptors and dopamine receptors. The hybrid trishomocubane-derived ligands (4-6) showed good selectivity for σ1 and σ2 receptors over multiple dopamine receptors. The molecular hybrid obtained from haloperidol and 4-azahexacyclo[5.4.1.02,6.03,10.0 5,9.08,11]dodecan-3-ol (4, σ1 K i = 27 nM, σ2 Ki = 55 nM) showed reduced affinity for D1-D5 dopamine receptors when compared to haloperidol itself. The compound with the greatest σ1 affinity in the series, benzamide 4 (σ1 Ki = 7.6 nM, σ2 Ki = 225 nM) showed a complete reversal of the subtype selectivity displayed by the highly σ2 selective parent benzamide, RHM-2 (3, σ1 Ki = 10412 nM, σ2 Ki = 13.3 nM).

PROTEASE-BINDING COMPOUNDS AND METHODS OF USE

Non-peptide, protease-binding compounds are described as useful in the detection, labelling, and inhibition of retroviral proteases. Aryl piperidinyl derivatives and other compounds related in structure have been found to be HIV-1 and HIV-2 protease-binding compounds.

Synthesis and structure-activity relationship of new piperidinyl and piperazinyl derivatives as antiallergics

A series of piperazinebenzothiazoles 3-5, piperazinebenzimidazoles 6-12, piperidinobenzothiazoles 14-45, piperidinobenzoxazoles 46-52 and piperidinobenzimidazoles 53-129 has been synthesized and their antiallergic activity evaluated by means of the passive cutaneous anaphylaxis (PCA) assay. Structure-activity relationships are discussed and related to classical antihistaminics. Piperidino derivatives with an aryl group linked to the nitrogen atom by an ethyl chain are the most active compounds, with ID50 1 mg/kg po. Some of these compounds are more potent antiallergics than astemizole and terfenadine.

Synthesis and Biological Characterization of α-(4-Fluorophenyl)-4-(5-fluoro-2-pyrimidinyl)-1-piperazinebutanol and Analogues as Potential Atypical Antipsychotic Agents

A series of 1-(pyrimidin-2-yl)piperazine derivatives were prepared and evaluated in receptor binding assays and in in vivo behavioral paradigms as potential atypical antipsychotic agents.Compound 16 (BMS 181100 (formerly BMY 14802)) emerged as the lead compound from within the series on the basis of its good activity and duration of action in the inhibition of both conditioned avoidance responding and apomorphine-induced stereotopy in the rat.Compound 16 not only failed to induce catalepsy in the rat but was quite effective in reversing the cataleptic effect of neurolepti c agents, thus indicating a low propensity for causing extrapyramidal side effects.In comparison to reference antipsychotic agents, 16 appeared to be less sedating and was relatively weaker in causing muscle incoordination.The compound was essentially inactive in binding to dopamine D2 receptors and its chronic administration to rats did not result in dopamine receptor supersensitivity.It exhibited modest to weak affinity for 5-HT1A and α1 receptors but was found to be a fairly potent ligand for ? binding sites (IC50 vs (+)--3-PPP = 112 nM).Although the resolved enantiomers of racemic 16 did not show dramatic differences from racemate or from each other in most tests, the R(+) enantiomer was up to 11-fold more potent than its antipode in binding to ? sites.Several studies have indicated that 16 may be a limbic-selective agent which may modulate dopaminergic activity by an indirect mechanism.The compound has been selected for clinical evaluation in the treatment of psychosis.

Agents for treatment of brain ischemia

A series of 5-halopyrimidin-2-ylpiperazinylalkyl derivatives having useful anti-ischemic properties for treatment and prevention of dirorders resulting from brain and/or spinal cord anoxia.

Antipsychotic 1-fluorophenylbutyl-4-(2-pyrimidinyl)piperazine derivatives

Disubstituted N,N-piperazinyl derivatives are disclosed wherein one substituent is a pyrimidin-2-yl ring and the other is a 4 carbon chain attached to a p-fluorophenyl ring at the terminal carbon. The terminal carbon of this butylene chain is also bonded to an oxygen atom as part of a carbonyl, carbinol, or ketal functionality. These compounds possess psychotropic properties, particularly atypical antipsychotic activity of good duration. By virtue of pre-clinical pharmacological testing, these compounds appear useful as potential antipsychotic agents which lack the typical movement disorder side-effects of standard antipsychotic agents.

Syntheses and hypotensive properties of substituted 2-aminotetralins

The synthesis and activity in the spontaneously hypertensive rat of several 4-(1,2,3,4-tetrahydronaphthyl-2-amino)-1-(4-fluorophenyl)-1-butanones is reported. Maximal antihypertensive activity was associated with 5,6-dimethoxy substitution in the aminotetralin moiety.

Synthesis of High Specific Activity - and Bromperidol and Tissue Distribution Studies in the Rat

A rapid synthesis of - and bromperidol with specific activity exceeding 10 000 Ci/mmol is described in which a trimethylstannylated analogue of bromperidol is used as a substrate for regiospecific no-carrier-added radiobromination. 4--4-hydroxypiperidino>-4'-fluorobutyrophenone was synthesized by the reaction of (trimethylstannyl)sodium with haloperidol and purified by preparative HPLC.Subsequent radiobromination with no-carrier-added 75Br- or 77Br- and in situ oxidation using H2O2/CH3COOH gave a corrected radiochemical yield of 35percent with a 30-min preparation time.Tissue distribution studies in the rat show a rapid and prolonged uptake into the brain, liver, and kidneys and consistently low blood concentrations that differ quantitatively from previous studies using relatively low specific activity bromperidol.Potential clinical applications for this high specific activity radiobrominated neuroleptic are discussed.

Synthesis of [82Br]bromperidol and preliminary tissue distribution studies in the rat.

A procedure is described for the preparation of [82Br]bromperidol with specific activity 440 muCi/mg. The incorporation of bromine-82 into the molecule was accomplished through Brackman and Smit's modification of the Sandmeyer reaction, during the last step of the synthetic route. This involved the formation of a complex between Cu82Br2 and nitric oxide gas in acetonitrile, which was then allowed to react with 4-[4-(aminophenyl)-4-hydroxy-piperidinyl]-1-(4-fluorophenyl)-1-butanone (aminoperidol, 10) to give [82Br]bromperidol in about 1.5 h. Cupric 82Br]bromide was prepared in situ from K82Br and CuSO4.5H2O. The radiochemical and chemical yields for the preparation of [82Br]bromperidol from K82Br were 10.4 and 12%, respectively. Preliminary tissue distribution studies with the labeled bromperidol in the rat showed that the uptake of radioactivity by the liver, brain, kidneys, and the lungs was very fast and was in the declining phase in the latter organs 15 min after iv administration.