1127-97-5

Usage

Preparation

Preparation by Fries rearrangement of m-chlo- rophenyl propionate (b.p.0.8 90°) with aluminium chloride, without solvent at 100° for 2 h (92%), at 140° for 2 h (89%), ? at 140–150° for 3 h, at 130° for 2 h (77%), at 165° for 1 h (72%), at 50° for 3 h (55%) or at 30–40° (53%)n nitrobenzene at 25° for 6 h (87%)Preparation by Fries rearrangement of m-chlorophenyl propionate with titanium tetrachloride at 100° for 2 h (75%) Also obtained by Friedel–Crafts reaction of propionyl chloride with m-chlorophenol in the presence of aluminium chloride Also obtained by isomerization of 2-chloro-4-hydroxypropiophenone on heating with aluminium chloride between 165° and 200° (30–70%).

InChI:InChI=1/C9H9ClO2/c1-2-8(11)7-4-3-6(10)5-9(7)12/h3-5,12H,2H2,1H3

Upstream product

• 108-43-0 3-monochlorophenol 
• 6285-05-8 4'-chloropropiophenone 
• 57479-70-6 2-methoxy-4-chlorobenzoic acid 
• 205320-02-1 4-chloro-N,2-dimethoxy-N-methylbenzamide 
• 36871-55-3 4-chloro-2-methoxypropiophenone 
• 6603-24-3 3-chlorophenyl propionate 

Downstream Products

• 36871-55-3 4-chloro-2-methoxypropiophenone 
• 77132-61-7 5-Chloro-2-[1-(phenyl-hydrazono)-propyl]-phenol 
• 77132-65-1 1-phenyl-2-(2'-hydroxy-4'-chlorophenyl)-3-methyl indole 
• 802256-08-2 5-Chlor-2-<2-dimethylaminomethyl-propionyl>-phenoxyessigsaeure 
• 1506-90-7 2-Propionyl-5-chlor-phenoxyessigsaeure 

Relevant academic research and scientific papers

Gram-Positive and Gram-Negative Antibiotic Activity of Asymmetric and Monomeric Robenidine Analogues

Desymmetrisation of robenidine (1: N′,2-bis((E)-4-chlorobenzylidene)hydrazine-1-carboximidhydrazide) and the introduction of imine alkyl substituents gave good antibiotic activity. Of note was the increased potency of two analogues against vancomycin-resistant Enterococci (VRE), one of which returned a MIC of 0.5 μg mL?1. Five analogues were found to be equipotent or more potent than the lead 1. Introduction of an indole moiety resulted in the most active robenidine analogue against methicillin-resistant S. aureus (MRSA), with a MIC of 1.0 μg mL?1. Imine C=NH isosteres (C=O/C=S) were inactive. Monomeric analogues were 16–64 μg mL?1 active against MRSA and VRE. An analogue that lacks the terminal hydrazide NH moiety showed modest Gram-negative activity at 64 μg mL?1. A 4-tert-butyl analogue was shown to be active against both Gram-positive and -negative strains at 16–64 μg mL?1. In general, additional modifications with aromatic moieties was poorly tolerated, except with concomitant introduction of an imine C-alkyl group. The activity of these analogues against MRSA and VRE ranged from 8 μg mL?1 to inactive (MIC>128 μg mL?1) with the naphthyl and indole analogues. Gram-negative activity was most promising with two compounds at 16 μg mL?1 against E. coli. Against P. aeruginosa, the highest activity observed was with MIC values of 32 μg mL?1 with another two analogues. Combined, these findings support the further development of the (E)-2-benzylidenehydrazine-1-carboximidamide scaffold as a promising scaffold for the development of antibiotics against Gram-positive and Gram-negative strains.

Broadening the catalyst and reaction scope of regio- and chemoselective C-H oxygenation: A convenient and scalable approach to 2-acylphenols by intriguing Rh(ii) and Ru(ii) catalysis

A unique Rh(ii) and Ru(ii) catalyzed C-H oxygenation of aryl ketones and other arenes has been developed for the facile synthesis of diverse functionalized phenols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by gram-scale synthesis of a few different 2-acylphenols. Its utility has been well exemplified in further applications in heterocycle synthesis and direct modifications of drug Fenofibrate.

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.

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.

Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants

Some novel 2-methyl-3-aminopropiophenones were synthesized and their centrally acting muscle relaxant activities were,evaluated for an inhibitory effect on the flexor reflex in rats. The structure-activity relationships are discussed. In this series 2-methyl-3-pyrrolidino-1-(4-trifluoromethylphenyl)-propan-1-one (28) showed significant centrally acting muscle relaxant activity. In addition, the activities of each enantiomer (28-(S) and (R)) were studied along with their acute toxicities. Compound 28-(R) was found to exhibit more potent activity and weaker acute toxicity than 28-(S). Accordingly, compound 28-(R) (NK433) is under development as a novel centrally acting muscle relaxant.

Certain alkylphenols used to control bacteria

The use of compounds of formula I STR1 wherein X represents chlorine or bromine and n denotes an integer from 1 to 6 for combating harmful microorganisms is disclosed.