100377-63-7

Basic information

• Product Name: VANILLIC ACID HYDRAZIDE
• Synonyms: AIDS058511;AIDS-058511;Oprea1_419318;Oprea1_661676;ST5054740;ZINC00405104;VANILLIC ACID HYDRAZIDE;4-HYDROXY-3-METHOXYBENZHYDRAZIDE
• CAS NO: 100377-63-7
• Molecular Formula: C₈H₁₀N₂O₃
• Molecular Weight: 182.18
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 100377-63-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 213-216°C
• Appearance: /
• Density: 1.307g/cm³
• Refractive Index: 1.594
• PKA: 8.61±0.20(Predicted)
• BRN: 3268276
• CAS DataBase Reference: VANILLIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: VANILLIC ACID HYDRAZIDE(100377-63-7)
• EPA Substance Registry System: VANILLIC ACID HYDRAZIDE(100377-63-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 100377-63-7(Hazardous Substances Data)

Usage

General Description

Vanillic acid hydrazide is a chemical compound that is derived from vanillic acid, a natural organic compound found in vanilla beans. It is commonly used in the field of organic synthesis and medicinal chemistry for its ability to react with aldehydes and ketones to form hydrazones, which are widely used in the synthesis of various pharmaceuticals and agrochemicals. Vanillic acid hydrazide is also known for its antioxidant properties and its potential as a precursor for the synthesis of novel bioactive compounds. Additionally, it has been studied for its potential use in the development of anti-inflammatory and antitumor agents. Overall, vanillic acid hydrazide is a versatile chemical with various potential applications in the fields of chemistry and medicine.

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

Upstream product

• 56681-66-4 3-methoxy-4-acetoxybenzoyl chloride 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 55828-12-1 4-hydroxy-3-methoxy-benzoic acid chloride 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 617-05-0 ethyl vanillate 

Downstream Products

• 90417-57-5 2-methoxy-4-[1,3,4]oxadiazol-2-yl-phenol 
• 122771-98-6 C₁₆H₁₇N₃O₃S 
• 1201594-66-2 4-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-2-methoxyphenol 

Relevant articles and documents

Synthesis of novel 5-(aroylhydrazinocarbonyl)escitalopram as cholinesterase inhibitors

A novel series of 5-(aroylhydrazinocarbonyl)escitalopram (58–84) have been designed, synthesized and tested for their inhibitory potential against cholinesterases. 3-Chlorobenzoyl- (71) was found to be the most potent compound of this series having IC50 1.80 ± 0.11 μM for acetylcholinesterase (AChE) inhibition. For the butyrylcholinesterase (BChE) inhibition, 2-bromobenzoyl- (76) was the most active compound of the series with IC50 2.11 ± 0.31 μM. Structure-activity relationship illustrated that mild electron donating groups enhanced enzyme inhibition while electron withdrawing groups reduced the inhibition except o-NO2. However, size and position of the substituents affected enzyme inhibitions.. In docking study of AChE, the ligands 71, 72 and 76 showed the scores of 5874, 5756 and 5666 and ACE of ?64.92,-203.25 and ?140.29 kcal/mol, respectively. In case of BChE, ligands 71, 76 and 81 depicted high scores 6016, 6150 and 5994 with ACE values ?170.91, ?256.84 and ?235.97 kcal/mol, respectively.

Novel arylcarbamate-N-acylhydrazones derivatives as promising BuChE inhibitors: Design, synthesis, molecular modeling and biological evaluation

A novel series of arylcarbamate-N-acylhydrazones derivatives have been designed and synthesized as potential anti-cholinesterase agents. In vitro studies revealed that these compounds demonstrated selective for butyrylcholinesterase (BuChE) with potent inhibitory activity. The compounds 10a-d, 12b and 12d were the most potent BuChE inhibitors with IC50 values of 0.07–2.07 μM, highlighting the compound 10c (IC50 = 0.07 μM) which showed inhibitory activity 50 times greater than the reference drug donepezil (IC50 = 3.54 μM). The activity data indicates that the position of the carbamate group in the aromatic ring has a greater influence on the inhibitory activity of the derivatives. The enzyme kinetics studies indicate that the compound 10c has a non-competitive inhibition against BuChE with Ki value of 0.097 mM. Molecular modeling studies corroborated the in vitro inhibitory mode of interaction and show that compound 10c is stabilized into hBuChE by strong hydrogen bond interaction with Tyr128, π-π stacking interaction with Trp82 and CH?O interactions with His438, Gly121 and Glu197. Based on these data, compound 10c was identified as low-cost promising candidate for a drug prototype for AD treatment.

Synthesis of novel triazoles and a tetrazole of escitalopram as cholinesterase inhibitors

A novel serie of escitalopram triazoles (60-88) and a tetrazole (89) have been synthesized and subjected to a study to establish the inhibitory potential of these compounds toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Some selectivity in inhibition has been observed. The 4-chlorophenyl- (75, IC50, 6.71 ± 0.25 μM) and 2-methylphenyl- (70, IC50, 9.52 ± 0.23 μM) escitalopram triazole derivatives depicted high AChE inhibition, while 2-fluorophenyl- (76, IC50 = 4.52 ± 0.17 μM) and 4-fluorophenyl- (78, IC50 = 5.31 ± 0.43 μM) have found to be excellent BChE inhibitors. It has also been observed that ortho, meta and para substituted electron donating groups increase the inhibition, while electron withdrawing groups reduce the inhibition. Docking analyses of inhibitors with AChE have depicted the binding energies for 70 and 75 as ΔGbind -6.42 and -6.93 kcal/mol, respectively, while ligands 76 and 78 have shown the binding affinity ΔGbind -9.04 and -8.51 kcal/mol, respectively, for BChE.

Pyrazole derivatives of medically relevant phenolic acids: Insight into antioxidative and anti-lox activity

Background: From the point of view of medicinal chemistry, compounds containing phenolic and pyrazolic moiety are significant since they are often constituents of bioactive compounds. Objective: The aims of this study were to synthesize pyrazole derivatives of medically relevant phenolic acids, confirm their structure, and evaluate their antioxidative and anti-LOX activities. Methods: Phenolic pyrazole derivatives were obtained, starting from esters of medically relevant phenolic acids. The structures of all obtained compounds were determined by NMR and IR spectroscopy, and UV-Vis spectrophotometry. In addition, the single-crystal X-ray diffraction was used. Pyrazole derivatives were tested for their in vitro antioxidative (DPPH assay), and lipoxygenase (LOX) inhibitory ac-tivities. Radical quenching mechanism was estimated using DFT and thermodynamic approach, while molecular docking was used to estimate the binding mode within the enzyme. Results: Pyrazole derivatives were obtained in high yields. The crystal structure of a new compound 3e was determined. Pyrazole derivative with catechol moiety 3d exhibited excellent radical scavenging ac-tivity, while compound 3b exhibited the best anti-LOX activity. Molecular docking study revealed that there is no direct interaction of any ligand with the active site of LOX-Ib, but pyrazoles 3a-e behave as inhibitors blocking the approach of linoleic acid to the active site. Conclusion: In this research, protocatechuic and vanillic acid pyrazole derivatives have been obtained for the first time. In vitro antioxidative assay suggests that pyrazole derivate of protocatechuic acid is a powerful radical scavenger, while anti-LOX assay indicates a pyrazole derivative with 4-hydroxyphenyl moiety.

Aromatic acyl hydrazone derivative and application thereof as NA inhibitor

The invention relates to an aromatic acyl hydrazone derivative as shown in a structural formula I, pharmaceutically acceptable salt and a pharmaceutical composition thereof, and application of the aromatic acyl hydrazone derivative and the pharmaceutically acceptable salt and the pharmaceutical composition in preparation of an influenza virus neuraminidase inhibitor, wherein R is one of trifluoromethyl, nitryl, 3-methyl-4-nitryl, 3-hydroxyl-4-nitryl, 3-nitryl-4-hydroxyl, hydroxyl, dihydroxyl, dinitryl, 3-methoxy-4-hydroxyl or trihydroxyl; Y is selected from hydroxyl, dihydroxyl, 2-hydroxyl-3-methoxy, 2-hydroxyl-4-methoxy,2-hydroxyl-5-methoxy,2-hydroxyl-6-methoxy,3-hydroxyl-2-methoxy,3-hydroxyl-4-methoxy,3-hydroxyl-5-methoxy,3-hydroxyl-6-methoxy,4-hydroxyl-2-methoxy,4-hydroxyl-3-methoxy,4-hydroxyl-3,5-dimethoxy, trihydroxyl, 4-hydroxyl-3-ethoxy, or 4-hydroxyl-3,5-dimethoxy; w is selected from CH or N; and z is selected from CH or N.