6036-14-2

Usage

Uses

Used in Pharmaceutical Industry:
(2-Naphthyloxy)acetic acid ethyl ester is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its anti-inflammatory and anti-cancer properties make it a valuable component in the development of new drugs for treating inflammation and cancer.
Used in Agrochemical Industry:
(2-Naphthyloxy)acetic acid ethyl ester is also used as a chemical intermediate in the synthesis of agrochemicals. Its potential applications in this industry include the development of new pesticides or herbicides to improve crop protection and yield.
Used in Organic Compounds Synthesis:
(2-Naphthyloxy)acetic acid ethyl ester is used as a chemical intermediate in the synthesis of various organic compounds. Its diverse range of properties and potential benefits make it a valuable component in the development of new organic compounds for various industrial applications.
Used in Central Nervous System Research:
Due to its impact on the central nervous system, (2-Naphthyloxy)acetic acid ethyl ester is used in research to explore its potential as a pharmaceutical drug for the treatment of neurological disorders or conditions affecting the central nervous system.

InChI:InChI=1/C14H14O3/c1-2-16-14(15)10-17-13-8-7-11-5-3-4-6-12(11)9-13/h3-9H,2,10H2,1H3

Upstream product

• 120-23-0 (2-naphthoyl)oxyacetic acid 
• 64-17-5 ethanol 
• 875-83-2 sodium 2-naphtholate 
• 105-39-5 chloroacetic acid ethyl ester 
• 135-19-3 β-naphthol 
• 36294-21-0 potassium 2-naphthoxide 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 35368-77-5 2-naphthalen-2-yloxy-acetamide 
• 75129-72-5 N-(2,5-dimethyl-1H-pyrrol-1-yl)-2-(naphthalen-2-yloxy)acetamide 
• 1398075-84-7 5-trifluoromethyl-5-hydroxy-4,5-dihydro-3-phenyl-1H-1-(2-naphthoxyacetyl)pyrazole 
• 1398076-36-2 5-trifluoromethyl-3-phenyl-1H-1-(2-naphthoxyacetyl)pyrazole 
• 434292-52-1 N-(4-hydroxyphenyl)-2-(naphthalen-2-yloxy) acetamide 
• 40926-77-0 (2-naphthyloxy)acetyl chloride 

Relevant academic research and scientific papers

Design, synthesis and in vitro antibacterial evaluation of naphthalen-2-yloxy based oxadiazole-2-thione derivatives

A series of novel Mannich bases 5-(naphthalen-2-yloxymethyl)-3-(substituted)aminomethyl-3H-[1,3,4]oxadiazole-2-thiones (5a-h) were synthesized by aminomethylation of substituted-1,3,4-oxadiazole-2(3H)-thione by equimolar concentration of primary or second

Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies

A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents

A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.

Synthesis and computer-aided analysis of the role of linker for novel ligands of the 5-HT6 serotonin receptor among substituted 1,3,5-triazinylpiperazines

A series of 2-amino-4-(4-methylpiperazin-1-yl)-1,3,5-triazines was designed based on previously published 2-amino-4-benzyl-(4-methylpiperazin-1-yl)-1,3,5-triazines in order to evaluate the role of a linker between the triazine moiety and an aromatic substituent for the human serotonin 5-HT6 receptor affinity. As new linkers two carbon atoms (ethyl or ethenyl) or an oxyalkyl chain (methoxy, 2-ethoxy, 2-propoxy) were introduced. Affinities of the compounds for the 5-HT6R as the main target, and for the 5-HT1AR, 5-HT7R and D2R as competitive ones, were determined in the radioligand binding assays. Docking to the 5-HT6R homology model was performed to support SAR analysis. Results showed that the branching of the methoxyl linker increased affinity for the human 5-HT6R whereas an unsaturated bond within the linker dramatically reduced desirable activity. Both experimental and theoretical studies confirmed the previously postulated beneficial role of the aromatic size for interaction with the 5-HT6R. Thus, the largest naphthyl moiety yielded the highest activity. In particular, 4-(4-methylpiperazin-1-yl)-6-(1-(naphthalen-1-yloxy)ethyl)-1,3,5-triazin-2-amine (24), the most potent 5-HT6R agent found (Ki = 23 nM), can be a new lead structure for further search and development.

Synthesis and Biological Evaluation of Substituted Indole and Its Analogs as Influenza A Virus Inhibitors

Influenza A virus (IAV), a highly pathogenic virus to human beings, is most susceptible to mutation and thus causes rapid, severe global pandemics resulting in millions of fatalities worldwide. Since resistance to the existing anti-influenza drugs is developing, innovative inhibitors with a different mode of action are urgently needed. The lead compound 6092B-E5 has proven to be an effective antiviral reagent in our previous work. Using the principles of substitution and bioisosterism of the indole ring, six series of novel anti-IAV target products were designed, synthesized and evaluated for their antiviral effect in this work. Compounds D1, D3, D9, G1, G3, G12 and G23 were identified as promising anti-IAV candidates with excellent anti-IAV efficacy (IC50 values of 3.06–5.77 μm) and low cytotoxicity (CC50 values up to and beyond 100 μm). This work represents a successful application of the substitution and bioisosteric replacement strategy for the discovery of novel antiviral molecules that can be used for further structural optimization.

New oxadiazole derivatives: Synthesis and appraisal of their potential as antimicrobial agents

Introduction: The escalating threat due to dwindling effect of antibiotics and challenge of tackling rising drug-resistant infections has gathered high focus in current medicinal research. Methods: In an attempt to find new molecules that can defeat microbial resistance, two new series of 2-[2-substituted ethenyl]-5-(substituted methoxy)-1,3,4-oxadiazole derivatives were synthesized. Various aromatic hydrazides were allowed to undergo cyclization to substituted oxadiazole-2- amines in the presence of cyanogen bromide and further condensed with different heterocyclic aldehydes to give new oxadiazole derivatives. The synthesized molecules were fully characterized by various spectral techniques and tested for antimicrobial activity. Results: Almost all the newly synthesized compounds especially (5g-5l) displayed remarkable growth inhibition against three bacterial strains: M. smegmatis, S. aureus, E. coli and fungi C. albicans. The antimicrobial activity was further confirmed by MIC assay against the same microorganisms. Oxadiazole 5g displayed promising activity with a MIC value of 0.025 mM for two bacteria and fungi, whereas MIC of this compound for E. coli was 0.1 mM. Other active compounds (5h-5l) also exhibited good MIC ranging between 0.313 to 5.0 mM against the selected microorganisms. Docking simulations were generated to explore the potential binding approaches of ligand 5g at the D-alanine:d-alanine ligase (Ddl) protein of E. coli and S. aureus. Conclusion: Molecule 5g was active even at a lower concentration and could probably act as a prospective lead molecule for targeting the drug resistant microorganisms.

N - acetyl glucosamine - 1 - phosphate urea glucoside acid radical transferase inhibitors and its preparation method and application

The invention discloses an N-acetylglucosamine-1-phosphate uridyltransferase inhibitor and a preparation method thereof. The chemical structural formula of the inhibitor is as shown in the specification. The invention also discloses application of the N-acetylglucosamine-1-phosphate uridyltransferase inhibitor. The N-acetylglucosamine-1-phosphate uridyltransferase inhibitor is designed, screened an synthesized on the basis of the target enzyme activity cavity structure characteristic, has excellent selectivity and specificity and conforms to the development principle of green pesticides; besides, the inhibitory activity IC50 value of the inhibitor to the N-acetylglucosamine-1-phosphate uridyltransferase reaches up to 10 mu M, and therefore, as a lead compound, the inhibitor is worthy of further optimized synthesis and has huge potential of being further developed into novel and efficient bactericides. The inhibitor has high inhibitory activity for the N-acetylglucosamine-1-phosphate uridyltransferase and can be used as the active ingredient of a Gram-negative bacterium bactericide.

Non-Covalent Synthesis as a New Strategy for Generating Supramolecular Layered Heterostructures

Noncovalent synthesis of stable heterostructures (graphene-BN, MoS2-graphene) of layered materials has been accomplished by a ternary host-guest complex as a heterocomplementary supramolecular motif. Besides being reversible, this supramolecular strategy to generate heterostructures may find uses in many situations.

Synthesis and antiproliferative evaluation of novel 2-(4H-1,2,4-triazole-3-ylthio)acetamide derivatives as inducers of apoptosis in cancer cells

In this study, a series of thiosemicarbazide derivatives 12–14, 1,2,4-triazol-3-thione derivatives 15–17 and compounds bearing 2-(4H-1,2,4-triazole-3-ylthio)acetamide structure 18–32 have been synthesized starting from phenolic compounds such as 2-naphthol, paracetamol and thymol. Structures and purity of the target compounds were confirmed by the use of their chromatographic and spectral data besides microanalysis. All of the synthesized new compounds 12–32 were evaluated for their anti-HIV activity. Among these compounds, three representatives 18, 19 and 25 were selected and evaluated by the National Cancer Institute (NCI) against the full panel of 60 human cancer cell lines derived from nine different cancer types. Antiproliferative effects of the selected compounds were demonstrated in human tumor cell lines K-562, A549 and PC-3. These compounds inhibited cell growth assessed by MTT assay. Compound 18, 19 and 25 exhibited anti-cancer activity with IC50values of 5.96?μM (PC-3?cells), 7.90?μM (A549/ATCC cells) and 7.71?μM (K-562?cells), respectively. After the cell viability assay, caspase activation and Bcl-2 activity of the selected compounds were measured and the loss of mitochondrial membrane potential (MMP) was detected. Compounds 18, 19 and 25 showed a significant increase in caspase-3 activity in a dose-dependent manner. This was not observed for caspase-8 activity with compound 18 and 25, while compound 19 was significantly elevated only at the dose of 50?μM. In addition, all three compounds significantly decreased the mitochondrial membrane potential and expression of Bcl-2.