34624-38-9

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Methoxyphenyl)ethanohydrazide is used as an antitubercular agent for its potential to treat tuberculosis, a bacterial infection that primarily affects the lungs. Its chemical structure allows it to target and inhibit the growth of Mycobacterium tuberculosis, the causative agent of the disease.
Used in Drug Development and Discovery:
2-(3-Methoxyphenyl)ethanohydrazide serves as a candidate for further research in drug development and discovery. Its unique chemical properties and structure make it a valuable compound for exploring new therapeutic agents and treatments for various diseases and conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(3-Methoxyphenyl)ethanohydrazide can be used as a building block or intermediate in the synthesis of more complex organic compounds. Its reactivity and functional groups make it a versatile component in the creation of new molecules with potential applications in various industries.
Used in Medicinal Chemistry:
2-(3-Methoxyphenyl)ethanohydrazide is utilized in medicinal chemistry for the design and synthesis of new pharmaceutical compounds. Its unique structure and properties can be exploited to develop novel drugs with improved efficacy, selectivity, and safety profiles for the treatment of various diseases and medical conditions.

InChI:InChI=1/C9H12N2O2/c1-13-8-4-2-3-7(5-8)6-9(12)11-10/h2-5H,6,10H2,1H3,(H,11,12)

Upstream product

• 1798-09-0 m-methoxyphenylacetic acid 
• 6834-42-0 3-methoxyphenylacetic acid chloride 
• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 18927-05-4 methyl (3-methoxyphenyl)acetate 

Downstream Products

• 1038304-53-8 4-amino-3-(3-methoxybenzyl)-1H-1,2,4-triazole-5(4H)-thione 
• 1394137-58-6 C₁₇H₁₃ClN₄OS 
• 1394137-59-7 C₁₇H₁₂F₂N₄OS 
• 720702-64-7 5-(3-methoxybenzyl)-4-(4-chlorophenyl)-2,4-dihydro-1,2,4-triazole-3-thione 
• 1412818-64-4 5-(3-methoxybenzyl)-4-(4-methoxyphenyl)-2,4-dihydro-1,2,4-triazole-3-thione 
• 1210977-64-2 5-(3-methoxybenzyl)-4-(2-methoxyphenyl)-2,4-dihydro-1,2,4-triazole-3-thione 
• 1353757-08-0 3-(3-methoxybenzyl)-4-(3-methoxyphenyl)-1H-1,2,4-triazol-5(4H)-one 
• 1353757-01-3 N-(3-methoxyphenyl)-2{2-(3-methoxyphenyl)acetyl}hydrazinecarboxamide 
• 1353757-07-9 3-(3-methoxybenzyl)-4-(2-methoxyphenyl)-1H-1,2,4-triazol-5(4H)-one 

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

4-(2-FLUOROPHENYL)-3-(3-METHOXYBENZYL)-1H-1,2,4-TRIAZOL-5(4H)-0NE AND ITS USE AS A THERAPEUTIC AGENT FOR METABOLIC DISEASE AND DEGENERATIVE BRAIN DISEASE

The present invention provides 4-(2-fluorophenyl)-3-(3-methoxybenzyl)-1H-1,2,4-triazole-5(4H)-one, or a pharmaceutically acceptable salt thereof, and uses thereof. A compound according to the present invention exhibits excellent effects on acetylcholinest

Synthesis, in-vitro, in-vivo anti-inflammatory activities and molecular docking studies of acyl and salicylic acid hydrazide derivatives

Over the course of time several drugs have been synthesized and are available in market for the treatment of inflammation. However, they were unable to cure effectively and associated with side effects. To effectively deal with such diseases, heterocycles and their derivatives have gained their special position. For this reason 1,3,4-oxadiazole (15–16), 1,2,4-triazole (17–18), Schiff base (19–24) and 3,5-disubstituted pyrazole (25) derivatives were synthesized starting from salicylic acid and acyl acid hydrazides (12–14) as COX-1 and COX-2 inhibitors. In vivo anti-inflammatory activities were also tested by carrageenan-induced mice paw edema against albino mice of any sex. Structures of all the synthesized compounds were confirmed by FT-IR and 1H NMR analysis. Schiff base derivative of 4-amiontirazole (24) with IC50 value of 1.76 ± 0.05 (COX-2) and 117.8 ± 2.59 emerged as potent COX-2 inhibitor. Furthermore, we also performed in-vivo anti-inflammatory investigations by using carrageenan induced paw edema test. From in-vivo anti-inflammatory activities, it was found that after 1 h the maximum percentage inhibition 15.8% was observed by compound 14 which is comparable with that of the standard drug followed by the compound 18 with percentage inhibition of 10.5%. After 3 h, the maximum percentage inhibition was observed by compound 18 with 22.2% and compound 14 with 16.7%. After 5 h the maximum percentage inhibition was observed by compound 18 with 29.4% followed by compound 16 with 23.5%. We further explore the mechanism of the inhibition by using docking simulations. Docking studies revealed that the selective COX-2 inhibitors established interactions with additional COX-2 enzyme pocket residues.

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.

Facile synthesis, crystal structure, DFT calculation and biological activities of 4-(2-fluorophenyl)-3-(3-methoxybenzyl)-1H-1,2,4-triazol-5 (4H)-one (5)

Background: In the past few decades, design, synthesis, and characterization of novel heterocyclic compounds with auspicious biological profile received the considerable attention of the scientific community. Among them, the small and simple organic molec

Novel triazole derivative with anti-inflammatory and anti-hyperglycemic activity and method for preparing the same

The present invention relates to a novel triazole derivative having anti-inflammatory and anti-diabetic activities, to a production method thereof, and to a pharmaceutical composition for preventing or treating inflammatory diseases and diabetic diseases, comprising the same. The novel triazole derivative according to the present invention has excellent inhibitory activity of type II collagen and COX-2 and exhibits anti-inflammatory activity, and thus can be used as a pharmaceutical composition for the preventing or treating inflammatory diseases. In addition, anti-diabetic activity is showed due to excellent inhibitory activities of alpha-glucosidase and alpha-amylase, thereby being able to be used as a pharmaceutical composition for preventing or treating diabetes diseases.COPYRIGHT KIPO 2017

A novel serine racemase inhibitor suppresses neuronal over-activation in vivo

Serine racemase (SRR) is an enzyme that produces D-serine from L-serine. D-Serine acts as an endogenous coagonist of NMDA-type glutamate receptors (NMDARs), which regulate many physiological functions. Over-activation of NMDARs induces excitotoxicity, which is observed in many neurodegenerative disorders and epilepsy states. In our previous works on the generation of SRR gene knockout (Srr-KO) mice and its protective effects against NMDA- and Aβ peptide-induced neurodegeneration, we hypothesized that the regulation of NMDARs’ over-activation by inhibition of SRR activity is one such therapeutic strategy to combat these disease states. In the previous study, we performed in silico screening to identify four compounds with inhibitory activities against recombinant SRR. Here, we synthesized 21 derivatives of candidate 1, one of four hit compounds, and performed screening by in vitro evaluations. The derivative 13J showed a significantly lower IC50 value in vitro, and suppressed neuronal over-activation in vivo.

Acetylcholinesterase inhibition activity of some quinolinyl substituted triazolothiadiazole derivatives

A series of aralkanoic acids was converted into aralkanoic acid hydrazides through their esters formation. The aralkanoic acid hydrazides upon treatment with carbon disulfide and methanolic potassium hydroxide yielded potassium dithiocarbazinate salts, which on refluxing with aqueous hydrazine hydrate yielded 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles. The target compounds, 3-aralkyl-6-(substitutedquinolinyl) [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles, were synthesized by condensing various quinolinyl substituted carboxylic acids with 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles in phosphorus oxychloride. The structures of the newly synthesized triazolothiadiazoles were characterized by IR, 1H NMR, 13C NMR, and elemental analysis studies. The structure of one of the 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles was unambiguously deduced by single crystal X-ray diffraction analysis. All the synthesized compounds were screened for their acetylcholinesterase inhibition activities. Four of the triazolothiadiazoles exhibited excellent acetylcholinesterase inhibition activities as compared to the reference inhibitor.

Synthesis, crystal structure, anti-inflammatory and anti-hyperglycemic activities of novel 3,4-disubstituted 1,2,4-triazol-5(4H)-one derivatives

A new series of 3,4-disubstituted 1,2,4-triazol-5(4H)-one 5a-r, bearing various methoxyphenyl, fluorophenyl, tolyl and phenyl groups, was synthesized by the dehydrocyclization of hydrazinecarboxamides 4a-r by refluxing in a 2 N sodium hydroxide solution. Hydrazinecarboxamides 4a-r was synthesized via the condensation of the corresponding aralkanoic acid hydrazides, 3a-g, with fluoro-, tolyl- and methoxyphenylisocyanates. The newly synthesized compounds (5ar) were characterized by IR, 1H NMR and 13C NMR analyses. The structure of one compound 5a was determined by single crystal X-ray diffraction analysis. All of the synthesized compounds were screened for their anti-inflammatory and anti-diabetic (α-glucosidase and α-amylase inhibition) activity to identify new drugs that might be useful in preventing damage related to diabetes and inflammation. Compounds 5j, 5k and 5m decrease the expression of type II collagen in a dose dependent manner; similarly 5l decrease the COX-2 expression of rabbit articular chondrocytes in a dose dependent manner possessing potent anti-inflammatory potential while some of derivatives including 5c, 5e, 5g and 5h cause inflammation. Meanwhile, excellent α-glucosidase and moderate α-amylase inhibitory profiles against carbohydrate modulating enzymes were demonstrated by compounds 5b, 5f, 5k and 5q compared to the reference standard acarbose, and compounds 5g, 5h, 5i, 5j, 5l and 5o exhibited moderate to low enzyme inhibition potential among the series.

Structure activity relationship of brevenal hydrazide derivatives

Brevenal is a ladder frame polyether produced by the dinoflagellate Karenia brevis. This organism is also responsible for the production of the neurotoxic compounds known as brevetoxins. Ingestion or inhalation of the brevetoxins leads to adverse effects such as gastrointestinal maladies and bronchoconstriction. Brevenal shows antagonistic behavior to the brevetoxins and shows beneficial attributes when administered alone. For example, in an asthmatic sheep model, brevenal has been shown to increase tracheal mucosal velocity, an attribute which has led to its development as a potential treatment for Cystic Fibrosis. The mechanism of action of brevenal is poorly understood and the exact binding site has not been elucidated. In an attempt to further understand the mechanism of action of brevenal and potentially develop a second generation drug candidate, a series of brevenal derivatives were prepared through modification of the aldehyde moiety. These derivatives include aliphatic, aromatic and heteroaromatic hydrazide derivatives. The brevenal derivatives were tested using in vitro synaptosome binding assays to determine the ability of the compounds to displace brevetoxin and brevenal from their native receptors. A sheep inhalation model was used to determine if instillation of the brevenal derivatives resulted in bronchoconstriction. Only small modifications were tolerated, with larger moieties leading to loss of affinity for the brevenal receptor and bronchoconstriction in the sheep model.