34800-90-3

Usage

Uses

Used in Chemical Syntheses:
1-Naphthaleneacethydrazide is used as a chemical intermediate for the synthesis of various compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable component in the development of new molecules and materials.
Used in Polymer Production:
1-Naphthaleneacethydrazide is used as a monomer or a building block in the production of polymers. Its incorporation into polymer chains can potentially influence the properties of the resulting materials, such as their stability, strength, or flexibility, depending on the specific application requirements.
Note: Due to the limited information available on 1-Naphthaleneacethydrazide, its uses are speculative and based on its structural composition. Further research and documentation are needed to confirm its applications and establish safety guidelines for its handling.

InChI:InChI=1/C12H12N2O/c13-14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8,13H2,(H,14,15)

Upstream product

• 2876-78-0 methyl 1-naphthylacetate 
• 86-87-3 naphth-1-yl acetic acid 
• 2122-70-5 ethyl 2-(1-naphthyl)acetate 
• 132-75-2 naphthalen-1-ylacetonitrile 

Downstream Products

• 57487-06-6 [1]naphthyl-acetic acid-(4-hydroxyimino-cyclohexa-2,5-dienylidenehydrazide) 
• 77052-80-3 C₁₉H₁₅Cl₂N₃OS 
• 77052-79-0 C₁₉H₁₅Cl₂N₃OS 
• 70284-65-0 Naphthalen-1-yl-acetic acid N'-(3-oxo-3-phenyl-1-p-tolyl-propyl)-hydrazide 
• 70284-68-3 Naphthalen-1-yl-acetic acid N'-[3-(4-bromo-phenyl)-3-oxo-1-phenyl-propyl]-hydrazide 
• 67759-88-0 1-(1-naphthylacetyl)-2-(3-chlorobenzylidene)hydrazine 
• 126381-29-1 3-(1-Naphthylmethyl)-4-(p-methoxyphenyl)-1,2,4-triazolin-5-on 
• 126381-30-4 3-(1-Naphthylmethyl)-4-(p-isopropoxyphenyl)-1,2,4-triazolin-5-on 
• 77052-84-7 4-(4-Fluoro-phenyl)-5-naphthalen-1-ylmethyl-4H-[1,2,4]triazole-3-thiol 
• 77052-87-0 4-(4-Chloro-2-methyl-phenyl)-5-naphthalen-1-ylmethyl-4H-[1,2,4]triazole-3-thiol 
• 77052-86-9 4-(3,4-Dichloro-phenyl)-5-naphthalen-1-ylmethyl-4H-[1,2,4]triazole-3-thiol 
• 77052-85-8 4-(2,4-Dichloro-phenyl)-5-naphthalen-1-ylmethyl-4H-[1,2,4]triazole-3-thiol 
• 77052-90-5 [4-(4-Fluoro-phenyl)-5-naphthalen-1-ylmethyl-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid 

Relevant academic research and scientific papers

Stimuli-responsive supramolecular hydrogel with white AIE effect for ultrasensitive detection of Fe3+ and as rewritable fluorescent materials

The development of fluorescent smart materials by introducing white light emission into supramolecular polymer hydrogels, and tuning their aggregation-induced emission (AIE) effect are essential for the manufacture of advanced functional materials. Herein, a novel bi-component supramolecular polymer hydrogel (NDG) was successfully constructed via a simple host-guest assembly process based on two easy-to-synthesize tripodal gelators (NTS and DTB). Strikingly, the NDG exhibits strong white aggregation-induced emission (WAIE), and can act as an AIE-based sensor for ultrasensitive detect Fe3+ and F?. The lowest limits of detection (LODs) are 5.33 × 10?9 M and 1.61 × 10?8 M, respectively. The xerogel of NDG exhibits nice adsorption and separation capacity for Fe3+, the adsorption rate reaches to 99.26%. In addition, the prepared NDG-based thin films can be used as rewritable fluorescent display material for the continuity detection of Fe3+ and F?. Due to the outstanding optical behavior of the NDG, it also be used as an “IMPLICATION” logic gate at the molecular level. The AIE hydrogel-guided enriches the self-assembly strategy of new supramolecular polymers, which also makes it become a good candidate for flexible optical materials.

Synthesis of new naphthyl aceto hydrazone-based metal complexes: Micellar interactions, DNA binding, antimicrobial, and cancer inhibition studies

In the present study, naphthyl acetohydrazide (HL) ligand was prepared and used for the synthesis of new six amorphous transition metal (Co(II), Ni(II), Cu(II), Zn(II), Pb(II), Cd(II)) complexes. All the compounds were characterized by elemental analysis, UV-vis, FT-IR, 1H- and 13C-NMR, and Matrix-Assisted Laser Desorption Ionization (MALDI). The solubilization study was carried out by estimating the interaction between the metal complexes with surfactants viz. sodium stearate (SS) and Cetyltrimethylammonium bromide (CTAB). UV-Visible spectroscopy was employed to determine partitioning and binding parameters, whereas electrical conductivity measurements were employed to estimate critical micellar concentration (CMC), the extent of dissociation, and free energy of micellization. The CT-DNA interaction of synthesized compounds with DNA represents the major groove binding. The synthesized ligand and metal complexes were also tested against bacterial and fungal strains and it has been observed that Cu(II) complex is active against all the strains except Candida albicans, while Cd(II) complex is active against all bacterial and fungal strains except Pseudomonas. Among all compounds, only the Pd(II) complex shows reasonable activity against cervical cancer HeLa cell lines, representing 97% inhibition.

Synthesis and biological evaluation of some new furoxan derivatives as anti-inflammatory agents

A new series of furoxan derivatives (3a-k) have been synthesized and characterized by their IR, 1H NMR and mass spectral data. All the compounds have been screened for their anti-inflammatory activity. The compounds 3a, 3b, 3f, 3g, and 3i which show significant anti-inflammatory activity have been further studied for their ulcerogenic activities and nitric oxide releasing properties. Furoxan derivative 3-memyl-4-[{2-(2-phenylacetyl)hydrazono}memyl]-furoxan 3f showed greater anti-inflammatory activity comparable to standard drug ibuprofen. The compound also showed reduced, ulcerogenicity and high nitric oxide releasing properties.

Synthesis and pharmacological screening: Sulfa derivatives of 2-pipecoline-bearing 1,3,4-oxadiazole core

An electrophile, 1-(4-(bromomethylbenzenesulfonyl)-2-methylpiperidine, was synthesized by the reaction of 2-methylpiperidine (2-pipecoline) and 4-bromomethylbenzenesulfonyl chloride in a weak basic medium under pH control. A series of nucleophiles, 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols, were synthesized from corresponding carboxylic acids in three steps. The title molecules were synthesized by coupling the electrophile to nucleophiles in an aprotic medium using LiH as an activator. The structures of all synthesized compounds were corroborated through IR, 1H NMR, and EI-MS techniques. All the compounds were screened for their pharmacological behavior, particularly, antibacterial and enzyme inhibitory activities. Notably efficient results were obtained against both gram-positive and gram-negative bacterial strains. Regarding enzyme inhibition, compounds were efficient against acetylcholinesterase and butyrylcholinesterase.

Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells

Melanin is a form of pigment that gives colour to human skin, hair and eyes. Whilst it protects against skin damage from the sun, accumulation of excessive amounts of epidermal melanin can lead to various dermatological disorders. This study aimed to evaluate the effects of three selected oxadiazoles on the o-diphenolase mushroom tyrosinase activity and their cytotoxic effects on SK-MEL-28 malignant melanoma cells. The results showed that compounds 1, 2 and 3 exhibited significant inhibition on the diphenolase activity of mushroom tyrosinase with IC50 values of 40.46 μM, 27.42 μM and 32.51 μM, respectively. Further kinetic studies revealed that compounds 1 (Ki = 3.8 μM) and 3 (Ki = 3.9 μM) exhibited a mixed-type inhibition while compound 2 (Ki = 0.7 μM) displayed a competitive-type inhibition as suggested by the Lineweaver-Burk plots. Molecular docking and dynamics simulations were also performed to understand the binding behaviour of compound 2 in the active site of tyrosinase. Finally, all three compounds displayed relatively low cytotoxicity to SK-MEL-28 cells up to 100 μM treatment via MTT assay.

Synthesis & characterization of 2-(substituted-phenyl)acetohydrazide analogs, 1,3,4-oxadiazoles, and 1,2,4-triazine Ring Systems: A novel class of potential analgesic and anti-inflammatory agents

The new series of 2-(substituted-phenyl)acetohydrazides analogs, S-alkylated 5-substituted-1,3,4-oxadiazoles-2-thione derivatives and 5-arylidene-3-substituted-1,2,4-triazines have been synthesized in good yields and characterized by IR, NMR, mass spectral and elemental analyses. All the synthesized compounds 4(a-d), 5(a-d), 7(a-b), and 8(a-f) are evaluated for their in vitro DPPH scavenging, antimicrobial activity, in vivo analgesic, anti-inflammatory activities. The results of the anti-inflammatory activity are supported by molecular docking study with mouse COX-1 (PDB ID: 2CZT) and COX-2 (PDB ID: 3LN1) enzymes to predict their putative interactions. Among all the assays conducted, the compounds 5-(4-bromophenyl)-3-(naphthalen-2-ylmethyl)-1,2,4-triazine (4d) and2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide (8a) have emerged as the most potent molecules.

Novel hybrid-pyrrole derivatives: Their synthesis, antitubercular evaluation and docking studies

Using novel hybrid molecules for the treatment of tuberculosis is one of the latest approaches. Keeping this concept in mind, thirty two hybrid compounds were synthesized, with pyrrole as one of the moieties, clubbed to coumarin, ibuprofen and isoniazid. The compounds were evaluated against Mycobacterium tuberculosis H37Rv strain. Compounds 7e and 8e exhibited MIC of 3.7 and 5.10 μg mL-1 and growth inhibition of 95% and 92%, respectively. These compounds were also active against single drug resistant bacterial strains. The compounds were devoid of cytotoxicity when tested against Vero African green monkey kidney cell line. Docking study was carried out on enoyl acyl carrier protein enzyme to provide some understanding into the mechanism of action of these compounds.

Substituted naphthalen-1-yl-acetic acid hydrazides: Synthesis, antimicrobial evaluation and QSAR analysis

A series of naphthalen-1-yl-acetic acid benzylidene/(1-phenyl-ethylidene)- hydrazides (1-36) was synthesized and tested, in vitro, for antiviral, antibacterial and antifungal activities. The antibacterial and antifungal screening results indicated that compounds having o-bromo, methoxy and hydroxy substitutents were the most active ones. The results of antiviral evaluation showed that none of the synthesized derivatives inhibited the viral infection at subtoxic concentrations. QSAR investigations revealed that the multi-target QSAR model was more effective in describing the antimicrobial activity than the one-target QSAR models. Further, it revealed the importance of the partition coefficient (log P) followed by energies of the highest occupied molecular orbital (HOMO) and topological parameters, molecular connectivity indices ( 1X, 3X and 3Xv) in describing the antimicrobial activity of substituted hydrazides.

Pharmacological screening for anti-inflammatory, analgesic activity of pyrazolyl derivatives along with molecular docking studies

The pyrazole derivatives were synthesized and pharmacologically evaluated for analgesic (tail flick) and anti-inflammatory (based on carrageenan-induced paw edema) activities. Compound 4k showed high potency as an anti-inflammatory agent after 3 and 4-h time intervals (P0.001) equipotent to indomethacin. They were devoid of ulcerogenic potential when administered at a dose of 30 mg/kg. The compounds, which showed less ulcerogenic action, also showed reduced malondialdehyde content (MDA), which is one of the byproduct of lipid peroxidation. Further docking studies of titled compounds was done to understand key interactions responsible for observed inhibition of COX enzyme. The most active compound 4k was found to have -11.192 kcal/mol, as the free energy of binding. Various other key interactions between the synthesized molecules and active site of COX-2 enzyme, responsible for the obtained pharmacological results were also reported. Most of the active compounds were docked well into the active sites of the receptor. Springer Science+Business Media, LLC 2011.

Synthesis and biological activity of oxadiazole and triazolothiadiazole derivatives as tyrosinase inhibitors

A series of 16 oxadiazole and triazolothiadiazole derivatives were designed, synthesized and evaluated as mushroom tyrosinase inhibitors. Five derivatives were found to display high inhibition on the tyrosinase activity ranging from 0.87 to 1.49 μM. Compound 5 exhibited highest tyrosinase inhibitory activity with an IC50 value of 0.87 ± 0.16 μM. The in silico protein-ligand docking using autodock 4.1 was successfully performed on compound 5 with significant binding energy value of -5.58 kcal/mol. The docking results also showed that the tyrosinase inhibition might be due to the metal chelating effect by the presence of thione functionality in compounds 1-5. Further studies revealed that the presence of hydrophobic group such as cycloamine derivatives played a major role in the inhibition. Piperazine moiety in compound 5 appeared to be involved in an extensive hydrophobic contact and a 2.9 hydrogen bonding with residue Glu 182 in the active site.