57676-51-4

Usage

Uses

Used in Pharmaceutical Industry:
(4-CHLORO-PHENYL)-ACETIC ACID HYDRAZIDE is used as an intermediary product for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
(4-CHLORO-PHENYL)-ACETIC ACID HYDRAZIDE is used as a key building block in the synthesis of agrochemicals, aiding in the production of effective and innovative agricultural products.
Used in Cancer Treatment Research:
(4-CHLORO-PHENYL)-ACETIC ACID HYDRAZIDE is used as a potential anti-tumor compound in ongoing research, exploring its application in the treatment of various types of cancer.
Used in Organic Compound Synthesis:
(4-CHLORO-PHENYL)-ACETIC ACID HYDRAZIDE is used as a valuable component in the synthesis of various organic compounds, contributing to the production of pharmaceuticals and other fine chemicals.
Used in Medicine:
(4-CHLORO-PHENYL)-ACETIC ACID HYDRAZIDE is used for its potential therapeutic benefits in medicine, with applications in the development of new treatments and therapies.
Used in Agriculture:
(4-CHLORO-PHENYL)-ACETIC ACID HYDRAZIDE is used in agriculture for its potential applications in the development of innovative and effective agricultural products, enhancing crop protection and yield.

InChI:InChI=1/C8H9ClN2O/c9-7-3-1-6(2-4-7)5-8(12)11-10/h1-4H,5,10H2,(H,11,12)

Upstream product

• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 
• 226957-05-7 tert-butyl 2-(2-(4-chlorophenyl)acetyl)hydrazinecarboxylate 
• 1878-66-6 4-chlorophenylacetic Acid 
• 25026-34-0 4-chlorophenacetyl chloride 
• 140-53-4 p-chlorobenzyl cyanide 

Downstream Products

• 34547-04-1 5-(4-chloro-benzyl)-3H-[1,3,4]oxadiazol-2-one 
• 896543-45-6 C₁₇H₁₈ClN₃O₃ 
• 187143-92-6 (4-Chloro-phenyl)-acetic acid [1-amino-2-cyano-eth-(E)-ylidene]-hydrazide 
• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 
• 1246847-98-2 N'-[(1E)-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-2-(4-chlorophenyl)acetohydrazide 
• 1246511-13-6 5-benzylidene-2-[2-(4-chloro-phenyl)-acetyl]-3-phenyl-2,5-dihydro-1H-[1,2,4]triazin-6-one 
• 1246511-25-0 2-[2-(4-chloro-phenyl)-acetyl]-5-(4-methyl-benzylidene)-3-phenyl-2,5-dihydro-1H-[1,2,4]triazin-6-one 
• 1246511-37-4 C₂₄H₁₈ClN₃O₃ 
• 1246511-61-4 C₂₄H₁₇Cl₂N₃O₂ 
• 1246511-49-8 C₂₅H₂₀ClN₃O₃ 
• 1246511-73-8 C₂₆H₂₃ClN₄O₂ 
• 1265015-10-8 C₂₇H₂₃Cl₂N₃O₅ 
• 93073-38-2 2-mercapto-5-(4-chlorobenzyl)-1,3,4-oxadiazole 
• 1356585-57-3 C₁₀H₉ClN₂OS 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of 3,4,5-trisubstituted-1,2,4-triazoles: High affinity and selective somatostatin receptor-4 agonists for Alzheimer's disease treatment

Somatostatin receptor-4 (SST4) is highly expressed in brain regions affiliated with learning and memory. SST4 agonist treatment may act to mitigate Alzheimer's disease (AD) pathology. An integrated approach to SST4 agonist lead optimization is presented herein. High affinity and selective agonists with biological efficacy were identified through iterative cycles of a structure-based design strategy encompassing computational methods, chemistry, and preclinical pharmacology. 1,2,4-Triazole derivatives of our previously reported hit (4) showed enhanced SST4 binding affinity, activity, and selectivity. Thirty-five compounds showed low nanomolar range SST4 binding affinity, 12 having a Ki 500-fold affinity for SST4 as compared to SST2A. SST4 activities were consistent with the respective SST4 binding affinities (EC50 600-fold selectivity over SST2A) display a favorable physiochemical profile, and was advanced to learning and memory behavior evaluations in the senescence accelerated mouse-prone 8 model of AD-related cognitive decline. Chronic administration enhanced learning with i.p. dosing (1 mg kg-1) compared to vehicle. Chronic administration enhanced memory with both i.p. (0.01, 0.1, 1 mg kg-1) and oral (0.01, 10 mg kg-1) dosing compared to vehicle. This study identified a novel series of SST4 agonists with high affinity, selectivity, and biological activity that may be useful in the treatment of AD. This journal is

Carbazole-based semicarbazones and hydrazones as multifunctional anti-Alzheimer agents

With the aim to combat a multi-faceted neurodegenerative Alzheimer’s disease (AD), a series of carbazole-based semicarbazide and hydrazide derivatives were designed, synthesized and assessed for their cholinesterase (ChE) inhibitory, antioxidant and biometal chelating activity. Among them, (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(pyridin-2-yl)hydrazinecarbothioamide (62) and (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(5-chloropyridin-2-yl)hydrazinecarbothioamide (63) emerged as the premier candidates with good ChE inhibitory activities (IC50 values of 1.37 μM and 1.18 μM for hAChE, IC50 values of 2.69 μM and 3.31 μM for EqBuChE, respectively). All the test compounds displayed excellent antioxidant activity (reduction percentage of DPPH values for compounds (62) and (63) were 85.67% and 84.49%, respectively at 100 μM concentration). Compounds (62) and (63) conferred specific copper ion chelating property in metal chelation study. Molecular docking studies of compounds (62) and (63) indicate strong interactions within the active sites of both the ChE enzymes. Besides that, these compounds also exhibited significant in silico drug-like pharmacokinetic properties. Thus, taken together, they can serve as a starting point in the designing of multifunctional ligands in pursuit of potential anti-AD agents that might further prevent the progression of ADs. Communicated by Ramaswamy H. Sarma.

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, Antimicrobial, and Antioxidant Screening of Aryl Acetic Acid Incorporated 1,2,4-Triazolo-1,3,4-Thiadiazole Derivatives

Some novel [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives were synthesized from aryl acetic acids. All the synthesized derivatives were selected for the screening of antibacterial potential against Gram-positive bacteria [Staphylococcus aureus (MTCC 3160) and Micrococcus luteus (MTCC 1538)] and Gram-negative bacteria [Escherichia coli (MTCC 1652) and Pseudomonas aeruginosa (MTCC 424)] and antifungal potential against Aspergillus niger (MTCC 8652) and Candida albicans (MTCC 227), and free radical scavenging activity through 2,2-diphenyl-2-picrylhydrazyl hydrate method. The compounds TH-4, TH-13, and TH-19 were found to be more potent antimicrobial agents compared to standard drugs. The compounds TH-3, TH-9, and TH-18 also showed significant antimicrobial activity. The compound TH-13 showed antioxidant activity with IC50 value better than the standard compound. The structures of all the synthesized compounds were confirmed by Fourier transform infrared, 1H-NMR, liquid chromatography–mass spectrometry, and CHN analyzer.

3,4,5-TRISUBSTITUTED-1,2,4-TRIAZOLES AND 3,4,5-TRISUBSTITUTED-3-THIO-1,2,4-TRIAZOLES AND USES THEREOF

The present disclosure describes novel compounds that are somatostatin receptor type 4 agonists.

Synthesis and Biological Activity of Anthranilic Diamide Derivatives Incorporating 1,3,4-oxadiazole or Nitrogen-containing Saturated Heterocyclic Moieties

A series of novel anthranilic diamide derivatives incorporating 1,3,4-oxadiazole or nitrogen-containing saturated heterocyclic moieties were synthesized, characterized, and evaluated for bacteriostatic activity against three phytopathogenic bacteria Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (R. solanacearum). The preliminary biological results indicated that most compounds exhibit bacteriostatic activity against three phytopathogenic bacteria. Among these compounds, compounds 6g, 6f, and 6i displayed better antibacterial activity. In the test with concentration of 200 μg/mL, antibacterial activity of compound 6i and 6j was 96%. In particular, the bacteriostatic activity displayed by compound 6h against Xoo is similar to the one displayed by commercial drug bismerthiazol.

Antiviral and Antibacterial Activities of N-(4-Substituted phenyl) Acetamide Derivatives Bearing 1,3,4-Oxadiazole Moiety

In this paper, a series of N-(4-substituted phenyl) acetamide derivatives bearing 1,3,4-oxadiazole moiety were synthesised. Preliminary bioassays revealed that these compounds not only exhibited favourable antiviral activities toward tobacco mosaic virus (TMV) but also demonstrated sustained inhibition activities against plant pathogenic bacteria, including Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri. Among the derivatives, TC8and TC20exerted the strongest curative activities against TMV, with half-maximal effective concentration (EC50) values of 239.5 and 236.2 μg/mL, respectively, which were comparable to that of ningnanmycin (EC50=273.2 μg/mL). Given their simple synthesis, the target compounds can serve as alternative antiviral candidates.

Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives

In this study, a series of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt caused by Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (R. solanacearum) via the turbidimeter test in vitro. Antibacterial bioassays indicated that most compounds demonstrated appreciable antibacterial bioactivities against Xoo and R. solanacearum. Among the title compounds, compound 4i demonstrated the best inhibitory effect against Xoo and R. solanacearum with half-maximal effective concentration (EC50) values of 14.69 and 15.14 μg/mL, respectively, which were even better than those of commercial agents Bismerthiazol and Thiodiazole Copper. In vivo antibacterial activities tests under greenhouse conditions revealed that the control efficiency of compound 4i against rice bacterial leaf blight and tobacco bacterial wilt were better than those of Bismerthiazol and Thiodiazole Copper. Meanwhile, field trials also indicated that compound 4i demonstrated appreciable control efficiency against rice bacterial leaf blight and tomato bacterial wilt.

Design, synthesis, and antibacterial activity against rice bacterial leaf blight and leaf streak of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivative

A series of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and leaf streak caused by Xanthomonas oryzae pv. oryzae and Xanthomonas oryzae pv. oryzicolaby via the turbidimeter test in vitro. Antibacterial bioassay results indicated that most compounds demonstrated good inhibitory effect antibacterial bioactivities against rice bacterial leaf blight and leaf streak. Among the title compounds, compound 6c demonstrated the best inhibitory effect against rice bacterial leaf blight and leaf streak with half-maximal effective concentration (EC50) values of 1.07 and 7.14 μg/mL, respectively, which were even better than those of commercial agents such as Bismerthiazol and Thiediazole Copper. In vivo antibacterial activities tests at greenhouse conditions demonstrated that the controlling effect of compounds 6c (43.5%) and 6g (42.4%) against rice bacterial leaf blight were better than those of Bismerthiazol (25.5%) and Thiediazole Copper (37.5%).

Inhibition of tobacco bacterial wilt with sulfone derivatives containing an 1,3,4-oxadiazole moiety

A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by 1H and 13C nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 μg/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5′c, 5′h, 5′i, and 5′j could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC50) at 39.8, 60.3, 47.9, and 32.1 μg/mL, respectively. Among them, compound 5′j was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)2] within the same concentration range. Field trials demonstrated that the control effect of compound 5′j against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.