32022-38-1

Usage

Uses

Used in Agricultural Industry:
2-(4-Chloro-2-methylphenoxy)acetic acid hydrazide is used as a herbicide for controlling the growth of broadleaf weeds and certain grasses. It functions by disrupting the hormone balance in these plants, thereby inhibiting their growth and aiding in effective weed management.
Used in Chemical Synthesis:
As a hydrazide, 2-(4-Chloro-2-methylphenoxy)acetic acid hydrazide is used as a starting material for the synthesis of hydrazone derivatives. These derivatives find applications in various chemical and pharmaceutical processes due to their unique properties.
Used in Pharmaceutical Industry:
2-(4-Chloro-2-methylphenoxy)acetic acid hydrazide has been studied for its potential use as a precursor in the synthesis of pharmaceutical compounds. Its ability to form hydrazone derivatives makes it a valuable component in the development of new drugs with diverse therapeutic applications.

InChI:InChI=1/C9H11ClN2O2/c1-6-4-7(10)2-3-8(6)14-5-9(13)12-11/h2-4H,5,11H2,1H3,(H,12,13)

Upstream product

• 2698-38-6 ethyl 2-(4-chloro-2-methylphenoxy)acetate 
• 94-74-6 MCPA 
• 2436-73-9 methyl 2-(4-chloro-2-methylphenoxy)acetate 
• 1570-64-5 2-methyl-4-chlorophenol 

Downstream Products

• 18248-43-6 4-allyl-1-(4-chloro-2-methylphenoxyacetyl)thiosemicarbazide 
• 328567-13-1 C₁₄H₁₄ClN₃O₂ 
• 356102-02-8 2-(4-chloro-2-methylphenoxy)-N'-[-(2-chlorophenyl)methylidene]acetohydrazide 
• 478382-70-6 2-(4-chloro-2-methylphenoxy)-N'-[(3,4-dichlorophenyl)methylidene]acetohydrazide 
• 356102-15-3 2-(4-chloro-2-methylphenoxy)-N'-[(2,6-dichlorophenyl)methylidene]acetohydrazide 
• 305864-57-7 2-(4-chloro-2-methylphenoxy)-N'-[-(2-fluorophenyl)methylidene]acetohydrazide 
• 474965-94-1 2-(4-chloro-2-methylphenoxy)-N'-[3-thienylmethylidene]acetohydrazide 
• 328113-75-3 2-(4-chloro-2-methylphenoxy)-N'-[-2-furylmethylidene]acetohydrazide 
• 329047-45-2 2-(4-chloro-2-methylphenoxy)-N'-[-(5-methyl-2-furyl)methylidene]acetohydrazide 
• 1637484-83-3 2-(4-chloro-2-methylphenoxy)-N'-[-(2,3-dihydroxyphenyl)methylidene]acetohydrazide 
• 478668-48-3 2-(4-chloro-2-methylphenoxy)-N'-[-(3,4-dihydroxyphenyl)methylidene]acetohydrazide 
• 356102-47-1 2-(4-chloro-2-methylphenoxy)-N'-[1-(4-hydroxyphenyl)ethylidene]acetohydrazide 
• 1637484-84-4 2-(4-chloro-2-methylphenoxy)-N'-[1-(2,4,6-trihydroxyphenyl)ethylidene]acetohydrazide 
• 51496-79-8 2-(4-chloro-2-methylphenoxy)-N'-[(4-hydroxyphenyl)methylidene]acetohydrazide 

Relevant academic research and scientific papers

Synthesis, structure analysis, DFT calculations and energy frameworks of new coumarin appended oxadiazoles, to regress ascites malignancy by targeting VEGF mediated angiogenesis

Ascites malignancy is a frequent cause of morbidity and presents significant management problems which occur in many cancers. Angiogenesis plays a major role in the prognosis of ascites tumor through Vascular Endothelial Growth Factor (VEGF). Inhibition o

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 biological evaluation of novel Ani9 derivatives as potent and selective ANO1 inhibitors

Anoctamin 1 (ANO1), a calcium-activated chloride channel, is highly expressed and amplified in a number of carcinomas including breast, pancreatic and prostate cancers. Downregulation of ANO1 expression and function significantly inhibits cell proliferation, migration, and invasion of various cancer cell lines. Development of potent and selective ANO1 inhibitors is currently desirable, which may provide a new strategy for cancer treatment. Our previous study revealed a new class of ANO1 inhibitor, (E)-2-(4-chloro-2-methylphenoxy)-N'-(2-methoxybenzylidene)acetohydrazide (Ani9) and structural optimization via chemical modification of Ani9 basic skeleton was undertaken for the development of more potent and specific inhibitors of ANO1. Structure-activity relationship studies with newly synthesized derivatives revealed a number of potent ANO1 inhibitors, among which 5f is the most potent inhibitor with an IC50 value of 22 nM. The selectivity analyses showed that 5f has excellent selectivity to ANO1 (>1000-fold over ANO2). In cellular assays, 5f significantly inhibited cell proliferation of PC3, MCF7, and BxPC3 cells expressing high levels of ANO1. In addition, 5f strongly reduced the protein levels of ANO1 in PC3 cells. This study will be useful in the development of ANO1 inhibitors for treatment of cancer and other ANO1-related diseases.

New Biguanides as Anti-Diabetic Agents, Part II: Synthesis and Anti-Diabetic Properties Evaluation of 1-Arylamidebiguanide Derivatives as Agents of Insulin Resistant Type II Diabetes

New 1-arylamidebiguanide hydrochloride salts were synthesized via reaction of hydrazide derivatives with dicyandiamide in acidic medium. The structure of the obtained derivatives was characterized by spectroscopic and elemental analysis tools. The anti-diabetic properties of the synthesized compounds were determined. Oral treatment of hyperglycemic rats with the synthesized biguanide derivatives showed a significant decrease of the elevated glucose in comparison with the anti-diabetic standard drug, metformin. The effects of the synthesized biguanide derivatives on the diabetic properties regarding liver function enzyme activities (AST, ALT, and ALP), lipid profiles (TC, TG, and TL), lipid peroxide, and nitrous oxide as well as histopathological characteristics were investigated and discussed.

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.

Phenoxyacetohydrazide schiff bases: β-glucuronidase inhibitors

Phenoxyacetohydrazide Schiff base analogs 1-28 have been synthesized and their in vitro β-glucouoronidase inhibition potential studied. Compounds 1 (IC50 = 9.20 ± 0.32 μM), 5 (IC50= 9.47 ± 0.16 μM), 7 (IC50 = 14.7 ± 0.19 μ