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
• Article Data: 4

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

• 106-39-8 bromochlorobenzene 
• 108-90-7 chlorobenzene 
• 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.