28236-62-6

Usage

Chemical Properties

light beige crystalline powder

InChI:InChI=1/C8H8Cl2N2O2/c9-5-1-2-7(6(10)3-5)14-4-8(13)12-11/h1-3H,4,11H2,(H,12,13)

Upstream product

• 774-74-3 2-(2,4-dichlorophenoxy)acetyl chloride 
• 108-95-2 phenol 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 1928-38-7 methyl 2,4-dichlorophenoxyacetate 
• 533-23-3 ethyl 2,4-dichlorophenoxyacetate 
• 120-83-2 2,4-dichlorophenol 

Downstream Products

• 51496-67-4 (2,4-dichloro-phenoxy)-acetic acid-(4-chloro-benzylidenehydrazide) 
• 74361-30-1 (2,4-Dichloro-phenoxy)-acetic acid [5-methyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 78794-15-7 2,4-Dichlorophenoxyacetyl-N⁴-benzyl-3-thiosemicarbazide 
• 35687-23-1 1‐(2,4‐dichlorophenoxy)acetyl‐4‐(1‐naphthyl)thiosemicarbazide 
• 56866-39-8 C₁₅H₁₉Cl₂N₃O₂S 
• 18233-39-1 4-allyl-1-(2,4-dichlorophenoxyacetyl)thiosemicarbazide 
• 56866-36-5 C₁₃H₁₇Cl₂N₃O₂S 
• 56866-35-4 2-(2-(2,4-dichlorophenoxy)acetyl)-N-ethylhydrazine-1-carbothioamide 
• 56866-37-6 C₁₆H₂₃Cl₂N₃O₂S 
• 54918-87-5 1-(2,4-dichlorophenoxy)acetyl-4-(4-iodophenyl)thiosemicarbazide 
• 54918-99-9 5-(2,4-dichloro-phenoxymethyl)-4-(4-ethoxy-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione 
• 54957-33-4 3-(2,4-dichlorophenoxymethyl)-4-(4-chlorophenyl)-5-mercapto-1,2,4-triazole 

Relevant academic research and scientific papers

Synthesis and cytotoxicity evaluation of [(2,4-dichlorophenoxy)methyl]-5-aryl-1,3,4-oxadiazole/4H-1,2,4-triazole analogues

We report herein the synthesis, characterization, and cytotoxicity evaluations of some newer oxadiazole and triazole analogues (5a-j). The cytotoxicity of all the title compounds were evaluated as per the National Cancer Institute protocol in a one-dose assay (10M) on nine different panels of 59 cancer cell lines. 2-f5-[(2,4-Dichlorophenoxy)methyl]-1,3,4-oxadiazol-2-ylgphenol (5e) showed the maximum cytotoxicity among the series of ten compounds. The cytotoxicity of 5e was comparable to that of the standard anticancer drug, 5-fluorouracil, and better than that of imatinib. The structure activity relationship was also discussed.

(2,4-Dichlorophenoxy)acetohydrazide

The title compound, C8H8Cl2N2O2, is an intermediate compound in the synthesis of one of the important 1,2,4-triazoles that possess diverse pharmacological activities.

Design, synthesis and molecular modelling of phenoxyacetohydrazide derivatives as Staphylococcus aureus MurD inhibitors

In the present work we synthesized a new series of phenoxyacetohydrazide functional compounds 4a-k and characterized by spectral data. Synthesized compounds were screened in vitro for their antibacterial activity. Compounds 4a, 4j and 4k exhibited inhibitory activity against S. aureus NCIM 5022 with MIC value of 64?μg/ml These compounds also exhibited activity against methicillin resistant S. aureus ATCC 43300 with MIC of 128?μg/ml. Among all the tested compounds 4c and 4j showed highest activity, respectively against B. subtilis NCIM 2545 and K. pneumoniae NCIM 2706. Only one compound i.e. 4d showed activity against another Gram-negative bacteria P. aeruginosa NCIM 2036 with MIC value of 64?μg/ml. Among three tested compounds, 4k exhibited highest inhibitory activity against S. aureus MurD enzyme with IC50 value of 35.80?μM. Further binding interactions of 4a-k with the modelled S. aureus MurD catalytic pocket residues is investigated with the extra-precision molecular docking and binding free energy calculation by MM-GBSA approach. The van der Waals energy term was observed to be the driving force for binding. Further, 50?ns molecular dynamics simulations were performed to validate the stabilities of 4j- and 4k-modelled S. aureus MurD. Graphic abstract: [Figure not available: see fulltext.]

Design, synthesis, in vitro and in silico studies of some novel triazoles as anticancer agents for breast cancer

Against the increasing incidence of breast cancer in postmenopausal women in recent years, a few clinically approved inhibitors and their side-effect profiles indicate the need for the development of new aromatase inhibitors. In this study, carried out to develop a new aromatase inhibitor, the triazole ring system was preferred because of its known activity in the field. The triazole ring, which is in the structure of the most commonly used aromatase inhibitors such as anastrazole and letrazole, was synthesized from the thiourea residue. Inhibitor structures were elucidated using the 1H-NMR, 13C-NMR, 2D-NMR, and HRMS spectroscopic methods. A cytotoxicity (MTT) test was performed to determine the anticancer activity of the compounds on breast (MCF7) carcinoma cell type. In addition, to determine selectivity of their action, the final compounds were screened against a healthy NIH3T3 cell line (mouse embryonic fibroblast cells). In terms of the MTT assay, it was observed that the calculated IC50 values of compound 5e for the NIH3T3 cell line were found to be higher than for the MCF7 cell lines. Considering the viability results, it was found that the selected compound 5e showed a favorable safety profile and that it has anticancer activities. It was determined by in vitro studies that compound 5e showed inhibition potential on the aromatase enzyme with an IC50 = 0.028 μM value. The docking study of compound 5e revealed that there is a strong interaction between the active sites of the human aromatase enzyme and the analyzed compound.

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

Synthesis and Insecticidal Evaluation of Novel N-pyridylpyrazole Derivatives Containing Diacylhydrazine/1,3,4-Oxadiazole Moieties

Two series of novel N-pyridylpyrazole derivatives containing diacylhydrazine/1,3,4-oxadiazole moieties were designed and synthesized based on the structure of chlorantraniliprole and characterized via 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. The preliminary bioassay indicated that some of the title compounds I and II exhibited larvicidal activities against Mythimna separata with 90–100% death rates at 500?mg/L. The further test showed that these compounds had weak insecticidal activity against Mythimna separata and Plutella xylostella at 200?mg/L and might be not suitable as insecticide lead compound for further optimization.

Synthesis and biological evaluation of some new furoxan derivatives as anti-inflammatory agents

A new series of furoxan derivatives (3a-k) have been synthesized and characterized by their IR, 1H NMR and mass spectral data. All the compounds have been screened for their anti-inflammatory activity. The compounds 3a, 3b, 3f, 3g, and 3i which show significant anti-inflammatory activity have been further studied for their ulcerogenic activities and nitric oxide releasing properties. Furoxan derivative 3-memyl-4-[{2-(2-phenylacetyl)hydrazono}memyl]-furoxan 3f showed greater anti-inflammatory activity comparable to standard drug ibuprofen. The compound also showed reduced, ulcerogenicity and high nitric oxide releasing properties.

Synthesis and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole moiety

Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 μg/mL against X. oryzae and 1.97-20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.

Synthesis and Herbicidal Activity of Some Novel Pyrazole Derivatives

Some novel pyrazole derivatives were designed and synthesized through multi-step reactions from substituted phenol as starting material. Their structures were confirmed by 1H NMR, FTIR, MS and elemental analysis. All these compounds were evaluated their herbicidal activity. The preliminary bioassay results indicated that some of title compounds displayed moderate herbicidal activity at 200 μg/mL. Among them, compounds 4-chloro-N'-(2-(2,5-dimethyl-phenoxy) acetyl)-3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-N'-(2-(2,4-dichlorophenoxy)acetyl)- 3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-3-ethyl-1-methyl-N'-(2-(m-tolyloxy) acetyl)-1H-pyrazole-5-carbohydrazide and 4-chloro-3-ethyl-1-methyl-N'-(2-(3-nitrophenoxy)acetyl)- 1H-pyrazole-5-car-bohydrazide possessed 95%, 100%, 95% and 95% inhibition against Brassica campestris respectively. In the further bioassay, the compound 6l exhibited excellent herbicidal activity either monocotyledon or dicotyledon plant at 150 g/ha.

Synthesis of acylhydrazines and, symmetrical and asymmetrical diacylhydrazines from carboxylic acid via the Vilsmeier reagent mediated process

(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) has been used as an efficient and convenient reagent for the one-pot synthesis of acylhydrazines and symmetrical and asymmetrical diacylhydrazines from carboxylic acids. This reaction proceeded smoothly under mild conditions and it is quite practical, since the starting carboxylic acids can be easily handled and stored. Cleanliness, simplicity of the method and good to excellent yield of products are other advantages of this method.