105533-69-5

Basic information

• Product Name: 1-(4-Chloro-5-fluoro-2-hydroxy-phenyl)-ethanone
• Synonyms: 1-(4-Chloro-5-fluoro-2-hydroxy-phenyl)-ethanone
• CAS NO: 105533-69-5
• Molecular Formula: C₈H₆ClFO₂
• Molecular Weight: 188.59
• Mol File: 105533-69-5.mol

Chemical Properties

• Melting Point: 72°C
• Appearance: /
• CAS DataBase Reference: 1-(4-Chloro-5-fluoro-2-hydroxy-phenyl)-ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Chloro-5-fluoro-2-hydroxy-phenyl)-ethanone(105533-69-5)
• EPA Substance Registry System: 1-(4-Chloro-5-fluoro-2-hydroxy-phenyl)-ethanone(105533-69-5)

Safety Data

• Hazardous Substances Data: 105533-69-5(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of acetyl chloride on 3-chloro4-fluorophenol with aluminium chloride at 95–100° (86%).

Upstream product

• 7440-44-0 pyrographite 
• 199586-28-2 1-Acetoxy-3-chloro-4-fluorobenzene 
• 2613-23-2 3-chloro-4-fluorophenol 
• 75-36-5 acetyl chloride 

Downstream Products

• 937817-47-5 (2-acetyl-5-chloro-4-fluorophenoxy)acetic acid ethyl ester 
• 245549-09-1 2-Phenyl-6-fluoro-7-chloro-4H-1-benzopyran-4-one 
• 880477-03-2 C₁₆H₉ClFNO₃ 
• 937816-99-4 (2-acetyl-5-chloro-4-fluorophenoxy)acetic acid 
• 1015485-96-7 2-acetyl-5-chloro-4-fluorophenyl-trifluoromethanesulfonate 

Relevant articles and documents

Optimization of chromone-2-carboxamide melanin concentrating hormone receptor 1 antagonists: Assessment of potency, efficacy, and cardiovascular safety

Evaluation of multiple structurally distinct series of melanin concentrating hormone receptor 1 antagonists in an anesthetized rat cardiovascualar assay led to the identification of a chromone-2-carboxamide series as having excellent safety against the chosen cardiovascular endpoints at high drug concentrations in the plasma and brain. Optimization of this series led to considerable improvements in affinity, functional potency, and pharmacokinetic profile. This led to the identification of a 7-fluorochromone-2-carboxamide (22) that was orally efficacious in a diet-induced obese mouse model, retained a favorable cardiovascular profile in rat, and demonstrated dramatic improvement in effects on mean arterial pressure in our dog cardiovascular model compared to other series reported by our group. However, this analogue also led to prolongation of the QT interval in the dog that was linked to affinity for hERG channel and unexpectedly potent functional blockade of this ion channel.

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

SPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS

The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating mammals suffering from the condition of being overweight.

ACYLATED PIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS

Certain novel N-acylated spiropiperidine derivatives are ligands of the human melanocortin receptor(s) and, in particular, are selective ligands of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevent

Identification of anthranilic acid derivatives as a novel class of allosteric inhibitors of hepatitis C NS5B polymerase

A series of potent anthranilic acid-based inhibitors of the hepatitis C NS5B polymerase has been identified. The inhibitors bind to a site on NS5B between the thumb and palm regions adjacent to the active site as determined by X-ray crystallography of the enzyme-inhibitor complex. Guided by both molecular modeling and traditional SAR, the enzyme activity of the initial hit was improved by approximately 100-fold, yielding a series of potent and selective NS5B inhibitors with IC50 values as low as 10 nM. These compounds were also inhibitors of the HCV replicon in cultured HUH7 cells.

Design, synthesis, and evaluation of novel 6-chloro-/fluorochromone derivatives as potential topoisomerase inhibitor anticancer agents

6-Chloro-2-pyrrolidino-/morpholino-/piperidino-/N-methylpiperazino-3- formyl-chromones (13-16) and 6-fluoro-2,7-di-morpholino-/piperidino-/N- methylpiperazino-3-formylchromones (17-19) have been synthesized as potential topoisomerase inhibitor anticancer agents, and evaluated, in vitro, against Ehrlich ascites carcinoma (EAC) cells, and also in vivo on EAC bearing mice. The compounds displayed promising anticancer activity under these test systems and shall serve as useful 'leads' for further design.

QSAR studies of paeonol analogues for inhibition of platelet aggregation

Various paeonol analogues were synthesized and tested in vitro as inhibitors of platelet aggregation. Structural properties (or descriptors) of paeonol analogues were calculated and the structure-activity relationships were determined. Several multiple linear and nonlinear regression models and back-propagation neural network model were tested and the latter using relative positive charge, hydration energy, and hydrophilic factor as inputs gave the best data fitting with R2 = 0.89 and qpre2=0.66. The correlation coefficient between antiplatelet inhibition activity with an interaction energy between the paeonol compounds with COX-1 enzyme is only 0.39.

Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor

The present invention is directed to compounds of formula (I), which antagonize of the effects of melanin-concentrating hormone (MCH) through the melanin concentrating hormone receptor which is useful for the prevention or treatment of eating disorders, weight gain, obesity, abnormalities in reproduction and sexual behavior, thyroid hormone secretion, diuresis and water/electrolyte homeostasis, sensory processing, memory, sleeping, arousal, anxiety, depression, seizures, neurodegeneration and psychiatric disorders.

Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them

Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or a diagnostic, and medicament comprising them Chromans of the formula I and of the formula 1a having the meanings R(A), R(B), R(C) and R(1) to R(8) indicated in the claims are outstandingly suitable for preparing a medicament for blocking the K+channel which is opened by cyclic adenosine monophosphate (cAMP); and further for preparing a medicament for inhibiting gastric acid secretion; for the treatment of ulcers of the stomach and of the intestinal region, in particular of the duodenum, for the treatment of reflux esophagitis, for the treatment of diarrheal illnesses, for the treatment and prevention of all types of arrhythmias including ventricular and supraventricular arrhythmias, and for the control of reentry arrhythmias and for the prevention of sudden heart death as a result of ventricular fibrillation.

Sulfonamide-substituted chromans, processes for their preparation, their use as medicament or diagnostic aid, and medicament comprising them

Chromans of formula I with the meanings of R(A), R(B) and R(1) to R(8) stated in the specification are suitable for producing a medicament for blocking the K+ channel that is opened by cyclic adenosine monophosphate (cAMP); also for producing medicaments