20143-41-3

Usage

Uses

Used in Agrochemical Industry:
(2-chlorophenoxy)acetyl chloride is used as a chemical intermediate for the production of herbicides and plant growth regulators. Its versatile functional groups allow for the synthesis of various agrochemical compounds that can effectively control or promote plant growth.
Used in Pharmaceutical Industry:
(2-chlorophenoxy)acetyl chloride is used as a building block in the synthesis of pharmaceuticals such as anti-inflammatories and anti-cancer drugs. Its unique structure enables the development of new and effective medications for various health conditions.
However, it is important to handle this chemical with caution, as it is corrosive and harmful if ingested or inhaled, and can cause severe skin and eye irritation. Proper safety measures should be taken during its production, storage, and use to minimize potential risks.

Upstream product

• 614-61-9 (2-chlorophenoxy)acetic acid 
• 95-57-8 2-monochlorophenol 
• 35535-81-0 sodium 2-chlorophenoxide 
• 36304-23-1 tert-butyl 2-(2-chlorophenoxy)acetate 
• 6956-85-0 Methyl (2-chlorophenoxy)acetate 

Downstream Products

• 115917-05-0 (2-chloro-phenoxy)-acetic acid-(3-oxo-androst-4-en-17β-yl ester) 
• 62095-50-5 (2-chloro-phenoxy)-acetic acid phenyl ester 
• 497087-21-5 N-[(2-chloro-phenoxy)-acetyl]-sulfanilic acid amide 
• 855602-42-5 (2-chloro-phenoxy)-ketene 
• 72192-83-7 3-(2-chloro-phenoxy)-4-(4-methoxy-phenyl)-1-(4-p-tolyl-thiazol-2-yl)-azetidin-2-one 
• 72192-70-2 3-(2-chloro-phenoxy)-4-(2-hydroxy-phenyl)-1-(4-phenyl-thiazol-2-yl)-azetidin-2-one 
• 72192-80-4 3-(2-chloro-phenoxy)-4-(2-hydroxy-phenyl)-1-(4-p-tolyl-thiazol-2-yl)-azetidin-2-one 
• 72192-93-9 3-(2-chloro-phenoxy)-1-(5-methyl-4-phenyl-thiazol-2-yl)-4-(4-nitro-phenyl)-azetidin-2-one 
• 64994-69-0 5-[(2-chloro-phenoxy)-acetyl]-2-(4-methoxy-phenyl)-5H-oxazolo[4,5-b]phenoxazine 
• 72192-37-1 2-(2-chloro-phenoxy)-N-(4-phenyl-thiazol-2-yl)-acetamide 
• 72192-61-1 2-(2-chloro-phenoxy)-N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-acetamide 
• 72192-43-9 2-(2-chloro-phenoxy)-N-(4-p-tolyl-thiazol-2-yl)-acetamide 
• 72192-73-5 3-(2-chloro-phenoxy)-4-(4-methoxy-phenyl)-1-(4-phenyl-thiazol-2-yl)-azetidin-2-one 
• 75057-59-9 6,7-dibromo-2-(2-chloro-phenoxymethyl)-benzo[d][1,3]oxazin-4-one 

Relevant academic research and scientific papers

Design and synthesis of α-phenoxy-N-sulfonylphenyl acetamides as Trypanosoma brucei Leucyl-tRNA synthetase inhibitors

Human African trypanosomiasis (HAT), caused by the parasitic protozoa Trypanosoma brucei, is one of the fatal diseases in tropical areas and current medicines are insufficient. Thus, development of new drugs for HAT is urgently needed. Leucyl-tRNA synthetase (LeuRS), a recently clinically validated antimicrobial target, is an attractive target for development of antitrypanosomal drugs. In this work, we report a series of α-phenoxy-N-sulfonylphenyl acetamides as T. brucei LeuRS inhibitors. The most potent compound 28g showed an IC50 of 0.70 μM which was 250-fold more potent than the starting hit compound 1. The structure-activity relationship was also discussed. These acetamides provided a new scaffold and lead compounds for the further development of clinically useful antitrypanosomal agents.

A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group

Abstract: A convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

Optimizing TRPM4 inhibitors in the MHFP6 chemical space

We recently reported 4-chloro-2-(2-chlorophenoxy)acetamido)benzoic acid (CBA) as the first potent inhibitor of TRPM4, a cation channel implicated in cardiac diseases and prostate cancer. Herein we report a structure-activity relationship (SAR) study of CBA resulting in two new potent analogs. To design and interpret our SAR we used interactive color-coded 3D-maps representing similarities between compounds calculated with MHFP6 (MinHash fingerprint up to six bonds), a new molecular fingerprint outperforming other fingerprints in benchmarking virtual screening studies. We further illustrate the general applicability of our method by visualizing the structural diversity of active compounds from benchmarking sets in relation to decoy molecules and to drugs. MHFP6 chemical space 3D-maps might be generally helpful in designing, interpreting and communicating the results of SAR studies. The modified WebMolCS is accessible at http://gdb.unibe.ch and the code is available at https://github.com/reymond-group/webMolCS for off-line use.

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.

Identification of potent and selective small molecule inhibitors of the cation channel TRPM4

Background and Purpose: TRPM4 is a calcium-activated non-selective cation channel expressed in many tissues and implicated in several diseases, and has not yet been validated as a therapeutic target due to the lack of potent and selective inhibitors. We sought to discover a novel series of small-molecule inhibitors by combining in silico methods and cell-based screening assay, with sub-micromolar potency and improved selectivity from previously reported TRPM4 inhibitors. Experimental Approach: Here, we developed a high throughput screening compatible assay to record TRPM4-mediated Na+ influx in cells using a Na+-sensitive dye and used this assay to screen a small set of compounds selected by ligand-based virtual screening using previously known weakly active and non-selective TRPM4 inhibitors as seed molecules. Conventional electrophysiological methods were used to validate the potency and selectivity of the hit compounds in HEK293 cells overexpressing TRPM4 and in endogenously expressing prostate cancer cell line LNCaP. Chemical chaperone property of compound 5 was studied using Western blots and electrophysiology experiments. Key Results: A series of halogenated anthranilic amides were identified with TRPM4 inhibitory properties with sub-micromolar potency and adequate selectivity. We also showed for the first time that a naturally occurring variant of TRPM4, which displays loss-of-expression and function, is rescued by the most promising compound 5 identified in this study. Conclusions and Implications: The discovery of compound 5, a potent and selective inhibitor of TRPM4 with an additional chemical chaperone feature, revealed new opportunities for studying the role of TRPM4 in human diseases and developing clinical drug candidates.

Synthesis and Biological Activity of 4-[(Substituted Phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one

A series of novel 4-[(substituted phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o were synthesized. Their structures were confirmed by IR,1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 4b, 4c, 4f, 4h, 4i, and 4j possess 90–100% inhibition against the growth of roots of both rape and barnyard grass at 10 mg/L. Moreover, the title compounds 4f, 4g, and 4h possess 75–89% inhibition against Botrytis cinerea at the concentration of 50 mg/L.

Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii

With multidrug resistant bacteria on the rise, novel antibiotics are becoming highly sought after. In 2008, eleven compounds were identified by high throughput screening as inhibitors of BasE, a key enzyme of the non-ribosomal peptide synthetase pathway found in Acinetobacter baumannii. Herein, we describe the preparation of four structurally similar heterocyclic lead compounds from that study, including one 1,2,5-oxadiazole. A further library of 30 analogues containing the oxadiazole moiety was then generated. All compounds were screened against Acinetobacter baumannii and their minimum inhibitory concentration data is reported, with (E)-3-(2-hydroxyphenyl)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acrylamide 32 found to have an MIC of 0.5 mM. This work provides the foundation for further investigation of 1,2,5-oxadizoles as novel inhibitors of A. baumannii.

Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate

(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.

Synthesis, Structure, and Properties of the 2-[5-(Aryloxyacetyl)-Amino-1,3,4-Thiadiazol-2-Ylthio] Propionate Derivatives

A series of novel 2-[5-(aryloxyacetyl)-amino-1,3,4-thiadiazol-2-ylthio] propionate derivatives were synthesized in high yield, and their structures were characterized by IR, 1H NMR, 13C NMR, and elemental analysis, coupled with one selected single-crystal X-ray structure determination. The herbicidal activities of target compounds were assessed. The preliminary bioassay results showed that some compounds exhibited moderate to strong herbicidal symptoms in preemergence and postemergence tests. At 150 g/ha, S. tritici. show tolerance, while E. crus-galli L., E. Dahuricus, A. retroflexus, and C. glaucum L. were killed or severely injured. The activity of some compounds was comparable to the commercial herbicide 2,4-D. A suitable electron-withdrawing substituent at the 2-and/or 4-position of the phenyl ring was essential for high herbicidal activity. Moreover, the antifungal activities of the compounds have also been studied. The compounds were found to possess broad-spectrum antifungal activity.

Synthesis, biological evaluation, and structure-activity relationships of potent noncovalent and nonpeptidic cruzain inhibitors as anti-Trypanosoma cruzi agents

The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (Ki = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, Ki = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.