41697-08-9

Basic information

• Product Name: 2-HYDROXY-4-METHOXYBENZENECARBOHYDRAZIDE
• Synonyms: ASISCHEM Z67645;2-HYDROXY-4-METHOXYBENZENECARBOHYDRAZIDE;2-HYDROXY-4-METHOXYBENZOHYDRAZIDE;2-HYDROXY-4-METHOXYBENZOIC ACID HYDRAZIDE;2-Hydroxy-4-methoxybenzohydrazide, 2-(Hydrazinocarbonyl)-5-methoxyphenol, 4-(Hydrazinocarbonyl)-3-hydroxyanisole
• CAS NO: 41697-08-9
• Molecular Formula: C₈H₁₀N₂O₃
• Molecular Weight: 182.18
• Product Categories: Carbonyl Compounds;Hydrazides;Organic Building Blocks
• Mol File: 41697-08-9.mol

Chemical Properties

• Melting Point: 172-176 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.307g/cm³
• Refractive Index: 1.594
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2-HYDROXY-4-METHOXYBENZENECARBOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-4-METHOXYBENZENECARBOHYDRAZIDE(41697-08-9)
• EPA Substance Registry System: 2-HYDROXY-4-METHOXYBENZENECARBOHYDRAZIDE(41697-08-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 41697-08-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Hydroxy-4-methoxybenzenecarbohydrazide is used as a chemical intermediate for the synthesis of various compounds. Its unique structure allows it to participate in a wide range of chemical reactions, making it a valuable component in the production of different organic compounds.
Used in Research and Development:
In the scientific community, 2-Hydroxy-4-methoxybenzenecarbohydrazide is used as a research compound to study its properties and potential applications. Researchers can explore its reactivity, stability, and interactions with other compounds, which can lead to the discovery of new chemical processes and products.
Used in Pharmaceutical Industry:
Although the information about its direct use in the pharmaceutical industry is limited, 2-Hydroxy-4-methoxybenzenecarbohydrazide may be used as a building block for the development of new drugs. Its unique structure could potentially be incorporated into the design of novel pharmaceutical compounds, contributing to the advancement of medicine.
Used in Material Science:
2-Hydroxy-4-methoxybenzenecarbohydrazide may also find applications in material science, where its properties can be utilized to develop new materials with specific characteristics. Its potential use in the synthesis of polymers, coatings, or other materials could lead to the creation of innovative products with unique properties.

InChI:InChI=1/C8H10N2O3/c1-13-5-2-3-6(7(11)4-5)8(12)10-9/h2-4,11H,9H2,1H3,(H,10,12)

Upstream product

• 5446-02-6 4-methoxymethylsalicylate 
• 2237-36-7 4-methoxysalicylic acid 
• 35031-00-6 ethyl 2-hydroxy-4-methoxybenzoate 

Downstream Products

• 1257843-08-5 2-(5-mercapto-1,3,4-oxadiazol-2-yl)-5-methoxyphenol 
• 1378258-45-7 5-methoxy-2-(5-((4-methoxybenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 
• 1378258-47-9 5-methoxy-2-(5-((2-nitrobenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 
• 1378258-48-0 5-methoxy-2-(5-((3-nitrobenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 
• 1378258-52-6 5-methoxy-2-(5-((4-nitrobenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 
• 1378258-31-1 2-(5-((2-chlorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-methoxyphenol 
• 1378258-32-2 2-(5-((3-chlorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-methoxyphenol 
• 1378258-34-4 2-(5-((4-chlorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-methoxyphenol 
• 1378258-36-6 2-(5-((2-fluorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-methoxyphenol 
• 1378258-37-7 2-(5-((4-fluorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-methoxyphenol 
• 1378258-39-9 5-methoxy-2-(5-((3-methylbenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 
• 1378258-42-4 5-methoxy-2-(5-((4-methylbenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 
• 1378258-44-6 5-methoxy-2-(5-((3-methoxybenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 
• 1357083-13-6 2-(5-(benzylthio)-1,3,4-oxadiazol-2-yl)-5-methoxyphenol 

Relevant articles and documents

Design, synthesis, in vitro and in silico studies of novel Schiff base derivatives of 2-hydroxy-4-methoxybenzamide as tyrosinase inhibitors

Due to the fact that tyrosinase is responsible for biosynthesis and regulation of melanins and browning food products, tyrosinase inhibitors can be favorable agents in cosmetics and medicinal industries. A series of novel 2-hydroxy-4-methoxybenzohydrazide were designed, synthesized, and their new application as tyrosinase inhibitors was also disclosed. Based on in vitro tyrosinase inhibitory assay, 4d as the strongest inhibitor of tyrosinase with an IC50 value of 7.57 μM showed approximately 2.5-fold better inhibition than kojic acid as positive control followed by two compounds 4b (IC50?= 8.19 ± 0.25 μM) and 4j (IC50?= 8.92 ± 0.016) which displayed preferable tyrosinase inhibitory activity. Detailed investigations on the mechanism of action of the 4d reported mix type of inhibition. More importantly, molecular modeling assessments proposed the ability of 4d for potential interaction with Cu (metal)-His (residue) within tyrosinase active site. Overall, 4d is a promising candidate for the development of anti-tyrosinase agents.

Synthesis, Antiproliferative and Antioxidant Activity of 3-Mercapto-1,2,4-Triazole Derivatives as Combretastatin A-4 Analogues

Two series of 3-mercapto-1,2,4-triazole derivatives containing alkoxy substituents different in size and position were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. The synthesized compounds were assessed for their antiproliferative activity against colon cancer cell line (SW480). The results indicated that the size and position of the alkoxy group significantly influenced the antiproliferative activity. The highest cancer cell growth inhibition values were observed for the compounds containing 3,4,5-trimethoxyphenyl groups in their structures (57.74, 54.14 and 60.70% at 50 μM for compounds 5a, 12b and 14, respectively). The synthesized compounds were also subjected to DPPH protocol for evaluating the antioxidant activity. The results showed that all compounds had moderate to high levels of antioxidant capacity as compared to ascorbic acid as standard, the highest free radical scavenging capacity of 75% was observed for compound 4a at 50 μM.

Gold (I) phosphine complex containing 5-phenyl-1, 3, 4-oxadiazole-2-thione and preparation method and application of gold (I) phosphine complex

The invention discloses a gold (I) phosphine complex containing 5-phenyl-1, 3, 4-oxadiazole-2-thione and a preparation method and application of the gold (I) phosphine complex, and belongs to the technical field of inorganic medicinal chemistry. The struc

Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents

A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 ± 0.2, 30.0 ± 1.2, 18.3 ± 1.4 μM, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 μM, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 μg/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study.

Synthesis, biological evaluation and molecular docking studies of novel 2-(1,3,4-oxadiazol-2-ylthio)-1-phenylethanone derivatives

In present study, a series of new 2-(1,3,4-oxadiazol-2-ylthio)-1- phenylethanone derivatives (6a-6x) as potential focal adhesion kinase (FAK) inhibitors were synthesized. The bioassay assays demonstrated that compound 6i showed the most potent activity, which inhibited the growth of MCF-7 and A431 cell lines with IC50 values of 140 ± 10 nM and 10 ± 1 nM, respectively. Compound 6i also exhibited significant FAK inhibitory activity (IC50 = 20 ± 1 nM). Docking simulation was performed to position compound 6i into the active site of FAK to determine the probable binding model.

Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents

A series of 1,3,4-oxadiazole derivatives derived from 4-methoxysalicylic acid or 4-methylsalicylic acid (6a-6z) have been first synthesized for their potential immunosuppressive activity. Among them, compound 6z displayed the most potent biological activity against lymph node cells (inhibition = 38.76% for lymph node cells and IC50 = 0.31 μM for PI3Kγ). The preliminary mechanism of compound 6z inhibition effects was also detected by flow cytometry (FCM) and the compound exerted immunosuppressive activity via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Docking simulation was performed to position compound 6z into the PI3Kγ structure active site to determine the probable binding model.

Synthesis, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents

A series of 2-(benzylthio)-5-aryloxadiazole derivatives have been designed and synthesized, and their biological activities are also evaluated for EGFR inhibitory activity. Fourteen compounds among the twenty compounds are reported for the first time. Their chemical structures are characterized by 1H NMR, MS, and elemental analysis. Anti-proliferative and EGFR inhibition assay results have demonstrated that compound 3e shows the most potent biological activity (IC50 = 1.09 μM for MCF-7 and IC50 = 1.51 μM for EGFR). Docking simulation has been performed to position compound 3e into the EGFR active site to determine the probable binding model, with an estimated binding free energy value of -10.7 kcal/mol. Compound 3e with potent inhibitory activity in tumor growth inhibition may be a promising anti-tumor leading compound for the further research.

Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents

A series of new 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety were synthesized. Antiproliferative assay results indicated that compounds 6o and 6u exhibited the most potent activity against gastric cancer cell SGC-7901, which was more potent than the positive control. Especially, compound 6o exhibited significant telomerase inhibitory activity (IC 50 = 2.3 ± 0.07 μM), which was comparable to the positive control ethidium bromide. Docking simulation was performed to position compound 6o into the active site of telomerase (3DU6) to determine the probable binding model.