20143-48-0

Usage

Uses

Used in Organic Synthesis:
(2,6-DIMETHYLPHENOXY)-ACETYLCHLORIDE is used as a reagent in organic synthesis for various chemical reactions. Its unique structure allows it to act as a versatile building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2,6-DIMETHYLPHENOXY)-ACETYLCHLORIDE is used as an intermediate in the synthesis of various drug molecules. Its ability to form stable bonds with other chemical entities makes it a valuable component in the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
(2,6-DIMETHYLPHENOXY)-ACETYLCHLORIDE is also used in the agrochemical industry as a precursor for the synthesis of various agrochemicals, such as pesticides and herbicides. Its chemical properties enable it to be incorporated into molecules that can effectively control pests and weeds in agricultural settings.
Used in Specialty Chemicals:
In the specialty chemicals industry, (2,6-DIMETHYLPHENOXY)-ACETYLCHLORIDE is used as a key component in the production of various specialty chemicals, such as dyes, fragrances, and other fine chemicals. Its unique structure and reactivity make it suitable for creating high-value products with specific applications.

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 32133-94-1 2,6-Dimethylphenylmercaptoessigsaeure 
• 6279-47-6 ethyl 2-(2,6-dimethylphenoxy)acetate 
• 13335-71-2 2-(2,6-dimethylphenoxy)acetic acid 

Downstream Products

• 898254-22-3 N-((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide 
• 192725-17-0 lopinavir 
• 192725-45-4 (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
• 1291079-74-7 N-(4-{[3-(4-tert-butylphenyl)isoxazol-5-yl]methoxy}phenyl)-2-(2,6-dimethylphenoxy)acetamide 
• 1291079-75-8 2-(2,6-dimethylphenoxy)-N-(4-{[3-(naphthalen-1-yl)isoxazol-5-yl]methoxy}phenyl)acetamide 
• 1132765-59-3 C₃₈H₅₀N₄O₅ 
• 1254734-64-9 R,S-2-(2,6-dimethylphenoxy)-N-(2-hydroxybutyl)acetamide 
• 1254734-63-8 S-(+)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide 
• 1254734-62-7 R-(-)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide 
• 1156110-85-8 R,S-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide 

Relevant academic research and scientific papers

Synthesis and characterization of novel analogues of lopinavir

The present work describes the identification, origin, synthesis, characterization and control of four novel analogues of lopinavir viz. leucine analogue of lopinavir, isoleucine analogue of lopinavir, methyl analogue of lopinavir and dihydroxy analogue of lopinavir.

AN IMPROVED PROCESS FOR PREPARATION OF LOPINAVIR AND ITS INTERMEDIATES THEREOF

The present invention generally relates to an improved process for preparation of lopinavir and its intermediates through formation of tartrate salt of compound of Formula (III).

Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration

Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Accumulation of farnesylated prelamin A in the nuclear envelope compromises cell division, impairs mitosis and induces an increased expression of inflammatory gene products. ZMPSTE24 has been proposed as a potential therapeutic target in oncology. A library of peptidomimetic compounds were synthesized and screened for their ability to induce accumulation of prelamin A in cancer cells and block cell migration in pancreatic ductal adenocarcinoma cells. The results of this study suggest that inhibitors of lamin A maturation may interfere with cell migration, the biological process required for cancer metastasis.

Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of amines, including aminoalkanols and amino acids

A series of 17 new phenoxyacetamides has been prepared via multistep chemical synthesis as a continuation of the research carried out by our group on di- and tri-substituted phenoxyalkyl and phenoxyacetyl derivatives of amines. The obtained compounds vary in an amide component, for example aminoalkanol or (un)modified amino acid moieties were introduced. The structures of selected products were confirmed by means of crystallographic methods. All 17 compounds were the subject of preliminary screening for potential anticonvulsant activity (MES, 6 Hz and/or scMET tests) and neurotoxicity (rotarod) in mice after intraperitoneal administration, while several active compounds were subsequently examined in additional models (e.g. MES and rotarod-rats, p.o. or i.p., hippocampal kindling-rats, i.p.). Finally, safety studies (cytotoxicity and cell proliferation assays on astrocytes, metabolic stability assessment, mutagenicity evaluation) were performed for several active compounds, including the most promising one (R-(?)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide, MES ED50 = 12.00 mg per kg b.w., rats, p.o.).

DERIVATIVES OF AMINOALKANOLS, METHOD OF OBTAINING OF AMINOALKANOLS AND THEIR USE

The subject of the invention is a group of new derivatives of aminoalkaπols, more specifically [(phenoxy)alkyl]aminoalkanols and [(phenoxy)acyl)aminoalkanols, their method of obtaining and their use for production of a medicine which is used in the prophylaxis, prevention and/or treatment of diseases or symptoms having neurological background and for production of a medicine with anticonvulsant activity, which is used in seizures of various origin, also in the limbic system, in myoclonic or sound-induced seizures, in psychomotor epilepsy, as well as in relieving neuropathic or inflammatory pain.

Calix[4]arene with lower-rim β-amino α,β-unsaturated ketones containing bis-chelating sites as a highly selective fluorescence turn-on chemosensor for two copper(II) ions

We report herein the synthesis of a fluorescence turn-on chemosensor, 25,27-bis{N-[1-(4-{[4-amino-4-(1-naphthyl)-2-oxo-3-butenyl]oxy}phenyl) aminocarbonyl]methoxy}-26,28-dihydroxycalix[4]arene (3b), which is highly selective toward Cu2+. The fluorescence intensity of 3b was enhanced upon adding [Cu(ClO4)2], which reached a maximum with approximately 4 equiv. of Cu2+ but then started to decrease in intensity at higher Cu2+ concentrations. Job plot experiments revealed a 1:2 binding stoichiometry of 3b with Cu2+. Based on 1H NMR titration results, we infer that there are two possible binding sites for Cu2+ in 3b: one at the lower-rim phenolic-OH and amide groups, and the second at the β-amino α,β-unsaturated ketone groups. It is important to note that during the complexation of 3b with [Cu(ClO4)2], the Cu2+ ions were reduced to Cu+ by both the phenolic OH and the amines of the β-amino α,β-unsaturated ketones. Furthermore, control compounds 6 and 9b were synthesized to clarify the possible binding sites of Cu2+ in 3b. By comparing the binding constants of 3b, 6, and 9b with Cu2+, we found that 3b exhibited a positive allosteric behavior toward the coordination of two Cu2+ ions. Calix[4]arene 3b shows high binding selectivity toward Cu2+ ions, which causes a dramatic enhancement of the fluorescence intensities at 341 and 452 nm by 4- and 40-fold, respectively. Chemosensor 3b can recognized two Cu2+ ions; both ions are reduced to Cu+ by both the phenolic-OH and the amines of the β-amino α,β- unsaturated ketones. Copyright

Synthesis and anticonvulsant activity of trans- and cis-2-(2,6- dimethylphenoxy)-N-(2- or 4-hydroxycyclohexyl)acetamides and their amine analogs

A group of trans- and cis-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl) acetamides (1-7) and -ethylamines (8-9) have been synthesized and investigated for their anticonvulsant activity. One of them, racemic trans-2-(2,6- dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamide proved to be the most effective in MES (mice, ip), exhibiting ED50 = 42.97 mg/kg b.w. and TD50 = 105.67 mg/kg b.w. It also proved protection in focal seizures (electric kindling, rats, ip) and it raises seizure threshold. The mechanism of action is inhibition of voltage-gated sodium currents and enhancement of GABA effect. Safety pharmacology assay on threshold tonic extension revealed no lowering of the seizure threshold.

PROCESS FOR THE PREPARATION OF SUBSTANTIALLY PURE (2S,3S,5S)-5-AMINO-2-N,N-DIBENZYLAMINO-3-HYDROXY-1,6-DIPHENYLHEXANE

The present invention relates to the purification of (2S,3S,5S)-5-amino-2-N,N-dibenzylamino-3-hydroxy-1,6-diphenylhexane (III) by making its crystalline acid addition salt, which can be used as such to produce Lopinavir/Ritonavir with high purity and yield. Formula III

Preliminary evaluation of anticonvulsant activity and neurotoxicity of some 1,4-substituted piperazine derivatives

A series of 1,4-piperazine derivatives was synthesized and evaluated for anticonvulsant activity in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole seizure threshold (ScMet) assays and for neurotoxicity (TOX). The compounds were only moderately effective. The anticonvulsant activity was accompanied by neurotoxicity. 1-[(4-Chlor-3- methylphenoxy)-acetyl]-4-(2-methoxyphenyl)-piperazine was also evaluated in six hertz seizure test (6-Hz) and showed good activity. At the dose of 100 mg/kg b. w. the compound produced 100% protection after 0.5 h without neurotoxic effect.

AN IMPROVED PROCESS FOR THE PREPARATION OF SUBSTANTIALLY PURE (2S,3S,5S)-5-AMINO-2-N,N-DIBENZYLAMINO-3-HYDROXY-1,6-DIPHENYLHEXANE

The present invention relates to the purification of (2S,3S,5S)-5-amino-2-N,N-dibenzylamino-3-hydroxy-1,6-diphenylhexane (III) by making its crystalline acid addition salt, which can be used as such to produce Lopinavir /Ritonavir with high purity and yield. Formula III