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Usage

Uses

Used in Pharmaceutical Development:
2-(2-Methoxyphenoxy)acetamide is used as a key intermediate in the synthesis of pharmaceuticals for its potential to contribute to the development of new drugs with anti-inflammatory and analgesic properties. Its presence in these formulations is attributed to its capacity to modulate biological responses, offering relief from inflammation and pain.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(2-Methoxyphenoxy)acetamide serves as a valuable building block for the creation of more complex organic molecules. Its reactivity and structural features make it suitable for use in the synthesis of a wide range of compounds, including those with potential applications in various industries.
Used in Medicinal Chemistry Research:
2-(2-Methoxyphenoxy)acetamide is utilized as a subject of study in medicinal chemistry research to explore its pharmacological properties and potential therapeutic applications. Scientists are investigating its interactions with biological targets to understand its mechanisms of action and to optimize its efficacy and safety in treating specific medical conditions.

InChI:InChI=1/C9H11NO3/c1-12-7-4-2-3-5-8(7)13-6-9(10)11/h2-5H,6H2,1H3,(H2,10,11)

Upstream product

• 13078-21-2 ethyl 2-(2-methoxyphenoxy)acetate 
• 5633-98-7 potassium guaiacolate 
• 79-07-2 Chloroacetamide 
• 13052-77-2 sodium 2-methoxyphenolate 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 1836-62-0 2-(2-methoxy-phenoxy)-ethylamine 
• 18655-51-1 2-(3-Aminopropyl)-1-methoxybenzene 

Relevant academic research and scientific papers

A phenoxy acetyl amine compound preparation method and phenoxy acetamide compounds

The invention belongs to the organic intermediates and the technical field of pharmaceutical intermediates, in particular to a phenoxy acetyl amine compound preparation method and phenoxy acetyl amine compound. The present invention provides a preparation method of the pervasive should be good, and green environmental protection, has better popularization and application value. The results show that the embodiment, the invention provides the above-mentioned method can prepare a plurality of phenoxy acetyl amine compound, and the yield can be 76%.

Synthesis and biological evaluation of 2-Phenoxyacetamide analogues, a novel class of potent and selective monoamine oxidase inhibitors

Monoamine oxidases (EC 1.4.3.4; MAOs), a family of FAD-containing enzymes, is an important target for antidepressant drugs. In this paper, a series of 2-phenoxyacetamide analogues were synthesized, and their inhibitory potency towards monoamine oxidases A (MAO-A) and B (MAO-B) were evaluated using enzyme and cancer cell lysate. 2-(4-Methoxyphenoxy)acetamide (compound 12) (SI = 245) and (2-(4-((prop-2- ynylimino)methyl)phenoxy)acetamide (compound 21) (IC50MAO-A = 0.018 μM, IC50MAO-B = 0.07 μM) were successfully identified as the most specific MAO-A inhibitor, and the most potent MAO-A/-B inhibitor, respectively. The inhibitory activities of these two compounds in living cells were also further evaluated utilizing HepG2 and SHSY-5Y cell lysates.

New serotonin 5-HT1A receptor agonists endowed with antinociceptive activity in vivo

We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR. Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-{[2-(2-ethoxyphenoxy) ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t1/2 ～ 3 h and CLint = 3.5 mL/min/kg, at 5 μM), and a low level of protein binding (25%, at 5 μM). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.

Discovery of a new series of 5-HT1A receptor agonists

Starting from compounds previously identified as α1-adrenoceptor antagonists that were also found to bind to the 5-HT1A receptor, in an attempt to separate the two activities, a new series of 5-HT1A receptor agonists was identified and shown to have high potency and/or high selectivity. Of these, compound 13, which combines high selectivity (5-HT1A/α1 = 151) and good agonist potency (pD2 = 7.82; Emax = 76), was found to be the most interesting.

1,3-Dioxolane-based ligands as a novel class of α1-adrenoceptor antagonists

1,3-Dioxolane-based compounds (2-14) were synthesized, and the pharmacological profiles at α1-adrenoceptor subtypes were assessed by functional experiments in isolated rat vas deferens (α1A), spleen (α1B), and aorta (α1D). Compound 9, with a pA2 of 7.53, 7.36, and 8.65 at α1A, α1B, and α1D, respectively, is the most potent antagonist of the series, while compound 10 with a pA2 of 8.37 at α1D subtype and selectivity ratios of 162 (α1D/α1A) and 324 (α1D/α1B) is the most selective. Binding assays in CHO cell membranes expressing human cloned α1-adrenoceptor subtypes confirm the pharmacological profiles derived from functional experiments, although the selectivity values are somewhat lower. Therefore, it is concluded that 1,3-dioxolane-based ligands are a new class of α1-adrenoceptor antagonists.