5341-58-2

Usage

Uses

Used in Pharmaceutical Industry:
3-HYDROXY-2-NAPHTHOIC ACID HYDRAZIDE is used as a chemical intermediate for the synthesis of various 2-(alkyl/arylamino)-5-(3-hydroxy-2-naphthyl)-1,3,4-thiadiazoles. These compounds have potential applications in the development of new drugs and therapeutic agents due to their diverse chemical structures and properties.
Used in Chemical Synthesis:
3-HYDROXY-2-NAPHTHOIC ACID HYDRAZIDE is used as a starting material for the synthesis of 3-hydroxy-2-naphthaldehyde, which can be further utilized in the production of other organic compounds with various applications in different industries, such as dyes, pigments, and pharmaceuticals.

InChI:InChI=1/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H

Upstream product

• 7163-25-9 ethyl 3-hydroxy-2-naphthanoate 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 92-70-6 3-Hydroxy-2-naphthoic acid 

Downstream Products

• 80571-75-1 isatine-3-hydroxy-2-naphtoylhydrazone 
• 321730-55-6 3-hydroxy-[2]naphthoic acid-(5-bromo-2-oxo-indolin-3-ylidenehydrazide) 
• 98471-24-0 3-(5-cyclohexyl-1H-[1,2,4]triazol-3-yl)-naphthalen-2-ol 
• 91989-50-3 3-hydroxy-[2]naphthoic acid-(2-chloro-benzylidenehydrazide) 
• 68181-06-6 3-hydroxy-N'-benzylidene-2-naphthohydrazide 
• 124843-39-6 benzoic acid N'-(3-hydroxynaphthalene-2-carbonyl)hydrazide 
• 101875-72-3 N-(4-chloro-benzoyl)-N'-(3-hydroxy-[2]naphthoyl)-hydrazine 
• 6962-30-7 3-hydroxy-2-naphthoyl azide 
• 97027-21-9 5-Chlormethyl-2-<3-hydroxy-naphthyl-(2)>-1,3,4-oxdiazol 
• 80571-23-9 picolylphenyl-3-hydroxy-2-naphtoylhydrazone 
• 80648-84-6 (E)-3-hydroxy-N′-(2-hydroxybenzylidene)-2-naphthohydrazide 
• 80648-85-7 (E)-3-hydroxy-N′-(2-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide 
• 80648-83-5 3-Hydroxy-naphthalene-2-carboxylic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 
• 80571-22-8 benzoylacetone-3-hydroxy-2-naphtoylhydrazone 

Relevant academic research and scientific papers

A new acylhydrazine N'-(1,3 dimethylbutylene)-3-hydroxy-naphthohydrazide based fluorescent sensor for the detection of Ni2+

In this paper, a novel hydrazide compound (N'-(1,3 dimethylbutylene)-3-hydroxy-naphthohydrazide) (BMH) was synthesized by a simple three-stage reaction and its chemical structure was confirmed by 1H NMR, 13C NMR and FTIR characterization. This compound was used as fluorescent sensor for the detection of Ni2+ based on photoluminescence quenching. The fluorescence quenching of BMH upon the addition of Ni2+ is due to the formation of coordination complex which was verified by bind model and density functional theory studies. The Ni2+ concentration dependent fluorescence quenching efficiency of BMH was examined and the detection conditions were optimized. There is a good linear relationship between the emission intensity quenching (ΔF = F0–F) and the Ni2+ concentration (c) between 80 nM and 2 μM and the detection limit is 60 nM. The simple preparation of the compound BMH and the high sensitivity of the fluorescent sensor hold great promise for the determination of Ni2+ in environment.

Binding mode dependent signaling for the detection of Cu2 +: An experimental and theoretical approach with practical applications

Two amido-schiff bases (3-Hydroxy-naphthalene-2-carboxylic acid pyren-1-ylmethylene-hydrazide and Naphthalene-2-carboxylic acid pyren-1-ylmethylene-hydrazide) have been synthesized having a common structural unit and only differs by a –OH group in the naphthalene ring. Both of them can detect Cu2 + ion selectively in semi-aqueous medium in distinctly different output modes (one detects Cu2 + by naked-eye color change where as the other detects Cu2 + by fluorescence enhancement). The difference in the binding of Cu 2 + with the compounds is the reason for this observation. The detection limit is found to be micromolar region for compound which contains –OH group whereas the compound without –OH group detects copper in nano-molar region. DFT calculations have been performed in order to demonstrate the structure of the compounds and their copper complexes. Practical utility has been explored by successful paper strip response of both the compounds. The biological applications have been evaluated in RAW 264.7.

A simple chemosensor for the dual-channel detection of cyanide in water with high selectivity and sensitivity

We have synthesized a simple chemosensor (HY) of acylhydrazones and used it for colorimetric detection of cyanide anions (CN-) in DMSO/H2O (3:7, v/v) mixed solvent. The simple chemosensor displays a specificity response for cyanide over other common anions (F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4-, ClO4-, and SCN-) in mixed solution. Upon treatment with cyanide, HY displayed a remarkable naked-eye and fluorogenic response, simultaneously with significant changes in its UV-visible and fluorescence spectra. Furthermore, competitive anions did not show any significant changes both in colour and emission intensity, indicating the high selectivity of the sensor to CN-. The absorption spectra detection limit of the chemosensor for cyanide was 8.34 × 10-7 M and the fluorescence spectra detection limit was 2.85 × 10-8 M. The cyanide test strips based on the chemosensor could serve as a convenient cyanide test kit. Furthermore, the chemosensor was successfully applied to the detection of cyanide in sprouting potatoes.

A chromone hydrazide Schiff base fluorescence probe with high selectivity and sensitivity for the detection and discrimination of human serum albumin (HSA) and bovine serum albumin (BSA)

The discrimination and identification of human serum albumin (HSA) and bovine serum albumin (BSA) is very important, which is due to the vital roles of two SAs in biological and pharmaceutical research. Based on structural screening and docking calculation from a series of homologues, a coumarin Schiff base fluorescent probe 3-hydroxy-N′-((4-oxo-4H-chromen-3-yl)methylene)-2-naphthohydrazide (HCNH) has been designed and synthesized, which could effectively discriminate HSA and BSA. The probe HCNH exhibited superior sensitivity toward HSA and BSA with the detection limits of 10.62 nM and 16.03 nM in PBS solution, respectively. The binding mechanism of HCNH with SAs was studied by Job's plot analysis, SA destruction and displacement assay. Molecular docking and DFT methods were utilized to provide deep insight into the spatial conformation change of HCNH and binding sites in HSA/BSA. The conformation of HCNH was significantly influenced by the microenvironment provided by HSA and BSA, therefore its fluorescence emission was affected correspondingly. Non-toxic probe HCNH could be successfully used for fluorescence bio-imaging of HSA in cancer cells, which is significantly different from normal cells and favors the application in medical diagnosis.

Discovery of an Orally Efficacious MYC Inhibitor for Liver Cancer Using a GNMT-Based High-Throughput Screening System and Structure-Activity Relationship Analysis

Glycine-N-methyl transferase (GNMT) downregulation results in spontaneous hepatocellular carcinoma (HCC). Overexpression of GNMT inhibits the proliferation of liver cancer cell lines and prevents carcinogen-induced HCC, suggesting that GNMT induction is a potential approach for anti-HCC therapy. Herein, we used Huh7 GNMT promoter-driven screening to identify a GNMT inducer. Compound K78 was identified and validated for its induction of GNMT and inhibition of Huh7 cell growth. Subsequently, we employed structure-activity relationship analysis and found a potent GNMT inducer, K117. K117 inhibited Huh7 cell growth in vitro and xenograft in vivo. Oral administration of a dosage of K117 at 10 mpk (milligrams per kilogram) can inhibit Huh7 xenograft in a manner equivalent to the effect of sorafenib at a dosage of 25 mpk. A mechanistic study revealed that K117 is an MYC inhibitor. Ectopic expression of MYC using CMV promoter blocked K117-mediated MYC inhibition and GNMT induction. Overall, K117 is a potential lead compound for HCC- and MYC-dependent cancers.

A highly selective colorimetric and fluorescent probe for quantitative detection of Cu2+/Co2+: The unique ON-OFF-ON fluorimetric detection strategy and applications in living cells/zebrafish

Identifying and detecting similar target cations through combining “turn on” and “turn off” fluorescence mechanism is effective and challenging. Now a new colorimetric and ON-OFF-ON fluorescent probe N′-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)-3-hydroxy-2-naphthohydrazide (L) was reported, which could detect Cu2+ and Co2+ in phosphate buffered CH3CH2OH-H2O solvent system. With the assistance of glutathione and pH adjustment, a unique ON-OFF-ON fluorescence detection strategy could be achieved for distinguishing Cu2+ and Co2+. The emission of probe could recover from the L-Cu2+ and L-Co2+ system by addition of GSH or adjusting pH value to 4, respectively, which is due to the abolishment of paramagnetic Cu2+/Co2+. Based on fluorescence titration experiments, the limit of detection was determined as 3.84 × 10?9 M and 4.55 × 10?9 M for Cu2+ and Co2+, respectively. Meanwhile, the detection limit reached 6.21 × 10?8 M for Cu2+ and 6.96 × 10?8 M for Co2+ according to absorbance signal output. Fast recognition of Cu2+/Co2+ can be achieved by obvious color changes from green to colorless under UV light, as well as from yellow to orange-red in room light. The binding mode of L toward Cu2+ and Co2+ have been systematically studied by Job's plot analysis, ESI-MS, IR and density functional theory calculations. Most strikingly, further practical applications of the probe L in fluorescence imaging were investigated in MCF-7 cells and zebrafish due to its low cytotoxicity and good optical properties, suggesting that L could serve as a fluorescent sensor for tracking Cu2+ and Co2+ in vivo.

Preparation of Acifluorfen-Based Ionic Liquids with Fluorescent Properties for Enhancing Biological Activities and Reducing the Risk to the Aquatic Environment

In this work, 12 novel herbicidal ionic liquids (HILs) based on acifluorfen were prepared by pairing with the fluorescent hydrazides or different alkyl chains for increasing activities and reducing negative impacts on the aquatic environment. The results showed that the fluorescence of coumarin hydrazide in the HILs was applied as the internal and supplementary light source to meet the requirement of light wavelength range of acifluorfen, which improved the phytotoxicity of acifluorfen to weeds by enhancing singlet oxygen generation with increased sunlight utilization. The herbicidal activities of HILs were related positively with the length of chain of cation under high light intensity and depended mainly on the fluorescence characteristic of the cation under low light intensity, and the double salt IL forms of acifluorfen containing coumarin hydrazide and n-hexadecyltrimethylammonium had enhanced efficacies against broadleaf weeds in the field. Compared with acifluorfen sodium, HILs had lower water solubility, better surface activity, weaker mobility in soils, and higher decomposition temperature. These results demonstrated that HILs containing different cations provided a wider scope for fine-tuning of the physicochemical and biological properties of herbicides and established a promising way for the development of environmentally friendly herbicidal formulations.

Crystallographic Elucidation of Stimuli-Controlled Molecular Rotation for a Reversible Sol-Gel Transformation

To get an idea about the most probable microporous supramolecular environment in the gel state, gelator molecule 1 has been crystallized from its gelling solvent (dimethylformamide). Crystal structure analysis of 1 shows a strong ?···πstacking interaction between the electron-deficient pentafluorophenyl ring and electron-rich naphthyl ring. The gelling solvent situated in the "molecular pocket" stitches the gelators through weak H-bonding interactions to facilitate the formation of an organogel. Scanning electron microscopy analysis exhibits a ribbonlike fibrous morphology that resembles the supramolecular arrangement of 1 in its crystalline state, as evidenced by powder X-ray diffraction. In the presence of external stimuli (tetrabutylammonium fluoride), the organogel of 1 disassembles into sol. This sol-gel transformation phenomenon has been explained on the basis of X-ray single-crystal analysis. Single crystals obtained from the sol state show that naphthylic-OH of 1 gets deprotonated, resulting in C-C bond rotation that plays a major role in the sol-gel transformation. Gelator 1 exhibits weak green fluorescence in the gel state, whereas it shows highly intense yellow fluorescence in the sol state. Furthermore, a reversible sol-gel transformation associated with changes in the spectroscopic properties has been observed in the presence of acids and fluoride ions, respectively.

Hydrazide derivatives and application thereof

The invention provides hydrazide derivatives and pharmaceutically acceptable salts thereof obtained through chemical synthesis. Pharmacological experiments prove that the compounds have the activity of resisting tumor cell proliferation, part of the compounds show the activity of inhibiting dimerization of protein DJ-1, and the compounds can be used for preparing drugs for treating, preventing andinhibiting DJ-1-associated tumor, type 2 diabetes as well as neurodegenerative diseases such as Parkinson s disease, Alzheimer's disease and the like. The general structural formula I of the compounds is shown in the description.

1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting D-alanine-D-alanine ligase in bacterio

The bacterial cell wall and the enzymes involved in peptidoglycan synthesis are privileged targets for the development of novel antibacterial agents. In this work, a series of 1-(2-hydroxybenzoyl)-thiosemicarbazides inhibitors of D-Ala-D-Ala ligase (Ddl) were designed and synthesized in order to target resistant strains of bacteria. Among these, the 4-(3,4-dichlorophenyl)-1-(2-hydroxybenzoyl)-3-thiosemicarbazide 29 was identified as a potent Ddl inhibitor with activity in the micromolar range. This compound, possessing strong antimicrobial activity including against multidrug resistant strains, was proven to act through a bactericidal mechanism and demonstrated very low cytotoxicity on THP-1 human monocytic cell line. Inhibition of Ddl activity by 29 was confirmed in bacterio using UPLC-MS/MS by demonstrating an increase in D-Ala intracellular pools accompanied by a commensurate decrease in D-Ala-D-Ala. Further structure-activity relationships (SARs) studies provided evidence that the hydroxyl substituent in the 2-position (R1) of the benzoylthiosemicarbazide scaffold is essential for the enzymatic inhibition. This work thus highlights the 1-(2-hydroxybenzoyl)-thiosemicarbazide motif as a very promising tool for the development of novel antibacterial compounds acting through an interesting mechanism of action and low cytotoxicity.