59995-68-5

Basic information

• Product Name: 4-[4-(4-CHLOROPHENYL)-4HYDROXY-1-PIPERIDINYL]-1-(4-CHLOROPHENYL)-1-BUTANONE
• Synonyms: 4-[4-(4-CHLOROPHENYL)-4HYDROXY-1-PIPERIDINYL]-1-(4-CHLOROPHENYL)-1-BUTANONE;HALOPERIDOL CHLORINATED ANALOG;HALOPERIDOL CHLORO-ANALOG;4-[4-(4-cholorophenyl)-4hydroxy-1-piperidinyl]-1-(4-chlorophenyl)-1-butanone;1-(3-(4-chlorobenzoyl)propyl)-4-hydroxy-4-(4-chlorophenyl)piperidine;1-(4-chlorophenyl)-4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidyl]butan-1-one;R 1854, 4-[4-(4-Cholorophenyl)-4hydroxy-1-piperidinyl]-1-(4-chlorophenyl)-1-butanone;R 1854
• CAS NO: 59995-68-5
• Molecular Formula: C₂₁H₂₃Cl₂NO₂
• Molecular Weight: 392.32
• Mol File: 59995-68-5.mol

Chemical Properties

• Melting Point: 154 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 550.4°C at 760 mmHg
• Flash Point: 286.7°C
• Appearance: white/solid
• Density: 1.261g/cm³
• Vapor Pressure: 5.98E-13mmHg at 25°C
• Refractive Index: 1.596
• Solubility: ethanol: 1 mg/mL
• PKA: 13.86±0.20(Predicted)
• CAS DataBase Reference: 4-[4-(4-CHLOROPHENYL)-4HYDROXY-1-PIPERIDINYL]-1-(4-CHLOROPHENYL)-1-BUTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(4-CHLOROPHENYL)-4HYDROXY-1-PIPERIDINYL]-1-(4-CHLOROPHENYL)-1-BUTANONE(59995-68-5)
• EPA Substance Registry System: 4-[4-(4-CHLOROPHENYL)-4HYDROXY-1-PIPERIDINYL]-1-(4-CHLOROPHENYL)-1-BUTANONE(59995-68-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 59995-68-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H23Cl2NO2/c22-18-7-3-16(4-8-18)20(25)2-1-13-24-14-11-21(26,12-15-24)17-5-9-19(23)10-6-17/h3-10,26H,1-2,11-15H2

Upstream product

• 108-90-7 chlorobenzene 
• 106-39-8 bromochlorobenzene 
• 235109-63-4 4-(4-chloro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 40877-09-6 4-chloro-1-(4-chlorophenyl)butan-1-one 

Downstream Products

• 52-86-8 haloperidol 

Relevant articles and documents

Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from: Mycobacterium tuberculosis to overcome kanamycin resistance

Tuberculosis (TB), caused by Mycobacterium tuberculosis (Mtb), is a deadly bacterial disease. Drug-resistant strains of Mtb make eradication of TB a daunting task. Overexpression of the enhanced intracellular survival (Eis) protein by Mtb confers resistance to the second-line antibiotic kanamycin (KAN). Eis is an acetyltransferase that acetylates KAN, inactivating its antimicrobial function. Development of Eis inhibitors as KAN adjuvant therapeutics is an attractive path to forestall and overcome KAN resistance. We discovered that an antipsychotic drug, haloperidol (HPD, 1), was a potent Eis inhibitor with IC50 = 0.39 ± 0.08 μM. We determined the crystal structure of the Eis-haloperidol (1) complex, which guided synthesis of 34 analogues. The structure-activity relationship study showed that in addition to haloperidol (1), eight analogues, some of which were smaller than 1, potently inhibited Eis (IC50 ≤ 1 μM). Crystal structures of Eis in complexes with three potent analogues and droperidol (DPD), an antiemetic and antipsychotic, were determined. Three compounds partially restored KAN sensitivity of a KAN-resistant Mtb strain K204 overexpressing Eis. The Eis inhibitors generally did not exhibit cytotoxicity against mammalian cells. All tested compounds were modestly metabolically stable in human liver microsomes, exhibiting 30-60% metabolism over the course of the assay. While direct repurposing of haloperidol as an anti-TB agent is unlikely due to its neurotoxicity, this study reveals potential approaches to modifying this chemical scaffold to minimize toxicity and improve metabolic stability, while preserving potent Eis inhibition. This journal is

Antifungal Compositions

Provided herein are antifungal compositions and methods of use thereof. The antifungal compositions include an antifungal agent and an antipsychotic agent or an antihistamine. The methods of use thereof include administering a composition including an antifungal agent and an antipsychotic or an antihistamine to a plant or animal in need thereof.

Structure-Kinetic Profiling of Haloperidol Analogues at the Human Dopamine D2 Receptor

Haloperidol is a typical antipsychotic drug (APD) associated with an increased risk of extrapyramidal side effects (EPSs) and hyperprolactinemia relative to atypical APDs such as clozapine. Both drugs are dopamine D2 receptor (D2R) antagonists, with contrasting kinetic profiles. Haloperidol displays fast association/slow dissociation at the D2R, whereas clozapine exhibits relatively slow association/fast dissociation. Recently, we have provided evidence that slow dissociation from the D2R predicts hyperprolactinemia, whereas fast association predicts EPS. Unfortunately, clozapine can cause severe side effects independent of its D2R action. Our results suggest an optimal kinetic profile for D2R antagonist APDs that avoids EPS. To begin exploring this hypothesis, we conducted a structure-kinetic relationship study of haloperidol and revealed that subtle structural modifications dramatically change binding kinetic rate constants, affording compounds with a clozapine-like kinetic profile. Thus, optimization of these kinetic parameters may allow development of novel APDs based on the haloperidol scaffold with improved side-effect profiles.

Phenylbutanol derivatives

Butyrophenone derivatives having excellent psychotropic activity and represented by the formula, SPC1 Wherein A represents a single or double bond linkage; R1 represents a hydrogen atom or a C1 - C4 alkyl group; R2, which is present only in case A represents a single bond linkage, represents a hydrogen atom, or a hydroxyl, C1 - C4 alkyl, or C1 - C4 alkoxy group; R3 represents a hydrogen atom, or a piperidino, pyrrolidino, morpholino, furyl, thienyl, C1 - C4 alkylamino, benzylamino, unsubstituted or halogen-substituted phenyl group, etc.; and X represents a hydrogen or halogen atom, or a C1 - C4 alkyl, C1 - C4 alkoxy, or trifluoromethyl group, can be prepared by reducing a benzoylpropionamide derivative of the formula, SPC2 Wherein A, R1, R2, R3 and X have the same meanings as defined above, to a phenylbutanol derivative of the formula, SPC3