15516-43-5

Usage

Uses

Used in Organic Synthesis:
(2-methylphenoxy)acetyl chloride is used as an acylating agent for introducing acetyl groups into various substrates. Its strong acylating properties make it a valuable reagent in the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2-methylphenoxy)acetyl chloride is utilized as a key intermediate in the synthesis of various drugs and pharmaceutical agents. Its ability to acylate organic compounds allows for the creation of new molecules with potential therapeutic applications.
Used in Chemical Research:
(2-methylphenoxy)acetyl chloride is also employed in chemical research as a reagent for studying the reactivity and properties of acetyl chloride groups in different chemical contexts. This helps researchers to better understand the mechanisms of acylation reactions and develop new synthetic strategies.
Used in Material Science:
In the field of material science, (2-methylphenoxy)acetyl chloride can be used as a precursor to develop new materials with specific properties. Its acylation capabilities can be harnessed to modify the structure and function of various materials, potentially leading to advancements in areas such as polymer chemistry and materials engineering.

Upstream product

• 95-48-7 ortho-cresol 
• 79-37-8 oxalyl dichloride 
• 1878-49-5 o-methylphenoxyacetic acid 
• 79-11-8 chloroacetic acid 
• 2989-17-5 methyl 2-methylphenoxy acetate 
• 4549-72-8 sodium o-cresolate 
• 13078-21-2 ethyl 2-(2-methoxyphenoxy)acetate 
• 1878-85-9 (2-methoxyphenoxy)acetic acid 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 100713-70-0 o-tolyloxy-acetic acid-(3-chloro-but-2ξ-enyl ester) 
• 122594-61-0 o-tolyloxy-acetic acid-(1-ethyl-3-dimethylamino-1-phenyl-propyl ester) 
• 76596-62-8 1-chloro-3-(o-tolyloxy)propan-2-one 
• 131253-20-8 o-tolyloxy-acetic acid-(2-diethylamino-ethylamide); hydrochloride 
• 31028-60-1 N-o-tolyloxyacetyl-glycine 
• 2021-06-9 4-o-tolyloxyacetyl-morpholine 
• 57628-14-5 N-[1,3,4]thiadiazol-2-yl-2-o-tolyloxy-acetamide 
• 57628-26-9 N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-2-o-tolyloxy-acetamide 
• 57628-32-7 N-(5-propyl-[1,3,4]thiadiazol-2-yl)-2-o-tolyloxy-acetamide 
• 64994-72-5 2-(4-methoxy-phenyl)-5-o-tolyloxyacetyl-5H-oxazolo[4,5-b]phenoxazine 
• 29728-49-2 6β-(2-o-tolyloxy-acetylamino)-penicillanic acid 
• 59090-62-9 2-(2-o-Tolyloxy-acetylamino)-benzoic acid 
• 78961-65-6 1-Aziridin-1-yl-2-o-tolyloxy-ethanone 
• 137537-09-8 1-Benzoimidazol-1-yl-2-o-tolyloxy-ethanone 

Relevant academic research and scientific papers

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Structure-based design, synthesis and evaluation of 2,4-diaminopyrimidine derivatives as novel caspase-1 inhibitors

Interleukin-1β converting enzyme contributes in various inflammatory and autoimmune diseases by maturing pro-inflammatory cytokines IL-1β, IL-18 and IL-33. Therefore, inhibition caspase-1 may provide a potential therapeutic strategy for the treatment of chronic inflammatory diseases. Here we have reported structure-based design, synthesis and biological evaluation of 2,4-diaminopyrimidine derivatives (6a-6w) as potential caspase-1 inhibitors. Six compounds 6m, 6n, 6o, 6p, 6q and 6r showed significant enzymatic inhibition with IC5 0 ranging from 0.022 to 0.078 μM. These compounds also displayed excellent cellular potency at sub-micromolar concentration. Moreover, molecular docking studies provided the useful binding insights specific for caspase-1 inhibition. All these results indicated that compounds 6m, 6n and 6o could be potential leads for the development of newer caspase-1 inhibitors as anti-inflammatory agents.

Isoflavone amide derivatives, their preparation method and medical use

The invention belongs to the field of medicinal chemistry, and relates to derivatives of isoflavones amides, as well as a preparation method and medical application of derivatives, in particular to the derivatives of the isoflavones amides with the general formula of (I) shown as the specification, the preparation method and the medical application of the derivatives, particularly the application of the derivatives of the isoflavones amides serving as medicaments for preventing or treating hyperlipemia, adiposis or type-II diabetes.

Discovery and development of a novel class of phenoxyacetyl amides as highly potent TRPM8 agonists for use as cooling agents

The paper presents the activity trends for a novel series of phenoxyacetyl amides as human TRPM8 receptor agonists. This series encompasses in vitro activity values ranging from the micromolar to the picomolar levels. Sensory evaluation of these molecules highlights their relevance as cooling agents for oral applications. The positive outcome of the complete evaluation of N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide resulted in its approval for Generally Recognized As Safe (GRAS) status by the Flavor & Extract Manufacturer Association (FEMA) as FEMA 4809.

Synthesis and biological evaluation of aryloxyacetamide derivatives as neuroprotective agents

A series of new aryloxyacetamide derivatives 10a-s and 14a-m are designed and synthesized. Their protective activities against the glutamate-induced cell death were investigated in differentiated rat pheochromocytoma cells (PC12 cells). Most compounds exhibited neuroprotective effects, especially for 10m, 10r, 14b and 14c, which showed potential protection of PC12 cells at three doses (0.1, 1.0, 10 μM). MTT assay, Hoechst 33342/PI double staining, and high content screening (HCS) revealed that pretreatment of the cells with 10m, 10r, 14b and 14c has significantly decreased the extent of cell apoptosis in a dose-dependent manner. The results of western blot analysis demonstrated these compounds suppressed apoptosis of glutamate-induced PC12 cells via caspase-3 pathway. These compounds can be lead compounds for further discovery of neuroprotective agents for treating cerebral ischemic stroke. Basic structure-activity relationships are also presented.

Formononetin derivatives and preparation methods and medical application thereof

The invention relates to the field of pharmaceutical chemistry, and relates to formononetin derivatives and preparation methods and medical application thereof, in particular to formononetin derivatives with the general formula as shown in (I), preparation methods thereof, pharmaceutical compositions containing the compounds and medical application of the derivatives and the pharmaceutical compositions, particularly, application of the derivatives and the pharmaceutical compositions serving as drugs for preventing or treating hyperlipidaemia or obesity or type-II diabetes. Please see the formula in the description.

Synthesis, antiproliferative activity and possible mechanism of action of novel 2-acetamidobenzamides bearing the 2-phenoxy functionality

Several new 2-(2-phenoxyacetamido)benzamides 17a-v, 21 and 22 were synthesized by stirring in pyridine the acid chlorides 16a-e and the appropriate5-R-4-R1-2-aminobenzamide 15a-e and initially evaluated in vitro for antiproliferative activity against the K562 (human chronic myelogenous leukemia) cell line. Some of synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). The most active compounds caused an arrest of K562 cells in the G0-G1 phase of cell cycle and induction of apoptosis, which was mediated by caspase activation.

Design, synthesis and structure-activity relationship studies of novel phenoxyacetamide-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1) has attracted extensive attention as a novel antidiabetic target in the last decade. Several FFA1 agonists reported in the literature have been suffered from relatively high molecular weight and lipophilicity. We have previously reported the FFA1 agonist 1. Based on the common amide structural characteristic of SAR1 and NIH screened compound, we here describe the continued structure-activity exploration to decrease the molecular weight and lipophilicity of the compound 1 series by converting various amide linkers. All of these efforts lead to the discovery of the preferable lead compound 18, a compound with considerable agonistic activity, high LE and LLE values, lower lipophilicity than previously reported agonists, and appreciable efficacy on glucose tolerance in both normal and type 2 diabetic mice.

Synthesis and biological evaluation of isoflavone amide derivatives with antihyperlipidemic and preadipocyte antiproliferative activities

A series of isoflavone amides were designed with isoflavone in place of the scaffold of 2-arylbenzoxazole as cholesterol ester transfer protein (CETP) inhibitors. Twelve new compounds were synthesized, and their inhibitory activities of CETP and preadipocyte proliferation were assayed. The hypolipidemic potency of the most effective compound HY-2c was further tested in vivo by hamster. The results indicate that HY-2c exhibited favorable antihyperlipidemic and preadipocyte antiproliferative activities.

Oxadiazole-isopropylamides as potent and noncovalent proteasome inhibitors

Screening of the 50 000 ChemBridge compound library led to the identification of the oxadiazole-isopropylamide 1 (PI-1833) which inhibited chymotrypsin-like (CT-L) activity (IC50 = 0.60 μM) with little effects on the other two major proteasome proteolytic activities, trypsin-like (T-L) and postglutamyl-peptide-hydrolysis-like (PGPH-L). LC-MS/MS and dialysis show that 1 is a noncovalent and rapidly reversible CT-L inhibitor. Focused library synthesis provided 11ad (PI-1840) with CT-L activity (IC50 = 27 nM). Detailed SAR studies indicate that the amide moiety and the two phenyl rings are sensitive toward modifications. Hydrophobic residues, such as propyl or butyl in the para position (not ortho or meta) of the A-ring and a m-pyridyl group as B-ring, significantly improve activity. Compound 11ad (IC50 = 0.37 μM) is more potent than 1 (IC50 = 3.5 μM) at inhibiting CT-L activity in intact MDA-MB-468 human breast cancer cells and inhibiting their survival. The activity of 11ad warrants further preclinical investigation of this class as noncovalent proteasome inhibitors.