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Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-N-naphthalen-1-yl-acetamide is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique molecular structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Organic Synthesis:
In the field of organic synthesis, 2-chloro-N-naphthalen-1-yl-acetamide serves as a valuable building block for the creation of more complex molecules. Its reactivity and functional groups make it a versatile starting material for the synthesis of a wide range of organic compounds, including those with potential applications in various industries.
Used in Chemical Research:
2-chloro-N-naphthalen-1-yl-acetamide is utilized as a research compound in various chemical studies. Its properties and reactivity are of interest to scientists who are exploring new reaction mechanisms, investigating the effects of molecular structure on chemical behavior, or developing novel methods for the synthesis of complex molecules. 2-chloro-n-naphthalen-1-yl-acetamide's potential applications in chemical research contribute to the advancement of knowledge in the field of chemistry.

InChI:InChI=1/C12H10ClNO/c13-8-12(15)14-11-7-3-5-9-4-1-2-6-10(9)11/h1-7H,8H2,(H,14,15)

Upstream product

• 134-32-7 1-amino-naphthalene 
• 79-04-9 chloroacetyl chloride 
• 593-71-5 Chloroiodomethane 
• 86-84-0 1-Naphthyl isocyanate 

Downstream Products

• 101578-10-3 (4-methyl-piperazino)-acetic acid-[1]naphthylamide 
• 63238-03-9 4-Amino-2-methylthio-N-α-naphthyl)-5-thiazolcarboxamid) 
• 86109-51-5 2-(benzo[d]oxazol-2-ylthio)-N-(naphthalen-1-yl)acetamide 
• 1042004-86-3 5-morpholin-4-yl-4-phenyl-thiophene-2-carboxylic acid naphthalen-1-yl-amide 
• 1003161-30-5 C₂₂H₂₃NO₂ 
• 928726-26-5 2-[(5-diphenylmethyl-1,3,4-oxadiazol-2-yl)sulfanyl]-N-(napthalen-1-yl)acetamide 
• 301678-99-9 C₁₈H₁₄ClNO₂ 

Relevant academic research and scientific papers

Polyamine ligand-mediated self-assembly of gold and silver nanoparticles into chainlike structures in aqueous solution: Towards new nanostructured chemosensors

1D Nanochain formation: The binding ability of a polyamine molecular linker (L)2- bearing different functional groups, which favors the self-assembling of silver (AgNPs) and gold nano-particles (AuNPs) into 1D nanochains in aqueous solution was explored. UV/Vis spectrophotometry and TEM were used to determine time-dependent structural changes associated with these 1D structure formations. Sensing of Hg2+ using AgNPs@ (L) 2- and AuNPs@ (L)2- assemblies was also carried out in aqueous solution.

Selective imaging of damaged bone structure (microcracks) using a targeting supramolecular Eu(III) complex as a lanthanide luminescent contrast agent

(Chemical Equation Presented) The synthesis and photophysical evaluation of a new supramolecular lanthanide complex is described which was developed as a luminescent contrast agent for bone structure analysis. We show that the Eu(III) emission of this complex is not pH dependent within the physiological pH range and its steady state emission is not significantly modulated by a series of group I and II as well as D-metal ions and that this agent can be successfully employed to image mechanically formed cracks (scratches) in bone samples after 4 or 24 h, using confocal laser-scanning microscopy.

Luminescent sensing of dicarboxylates in water by a bismacrocyclic dinuclear Eu(III) conjugate

The design, synthesis, and characterization of a novel dinuclear Eu(III) bismacrocyclic conjugate 1·Eu2 as a delayed luminescent lanthanide sensor for dicarboxylates is discussed. The sensor was shown to bind small dicarboxylic acids such as aspartic, malonic, succinic, or glutaric acid in pH 6.5 solutions. However, only malonic acid gave rise to selective Eu(III) luminescent enhancements, as the emission was reduced for all of the other acids.

Zinc selective chemosensors based on the flexible dipicolylamine and quinoline

Zinc sensor molecules containing quinoline have been synthesized, which show fluorescence in the presence of Zn2+. The nitrogen in quinoline is critical to fluorescence and fluorescence enhancement is promoted by deprotonating the sensor's amide. One of the sensors is highly selective for Zn2+ over Cd2+ and other cations such as Hg2+, Fe2+, Mn2+ and Ca2+. This selectivity can be attributed to the increased absorption of the sensor in the presence of Zn 2+ and the strong binding of Zn2+. Structural studies, including X-ray and NMR, show the ability of dipicolylamine (DPA) to bind in facial and meridional manners to Zn2+. Crystal structures of different compounds show Zn2+ coordinating to three, four, and five nitrogens from the compounds. They also indicate that the selectivity of DPA containing compounds towards Zn2+ may originate from Zn2+ being stable in different coordination environments.

Naphthalene appended 2,5-diketopiperazine towards fluorometric response of dihydrogenphosphate

Naphthalene-based 2,5-diketopiperazine 1 has been synthesized in two steps with moderate yield. The compound shows water templated hydrogen bonded assemblies in the solid state and exhibits unique hydrogen bond mediated emission properties in solution. The monomer emission of 1 in CHCl3 containing 0.1% DMSO is significantly quenched in the presence of large excess of dihydrogenphosphate anion and aliphatic dicarboxylic acids of different chain lengths followed by the appearance of a new peak of moderate intensity at higher wavelength for excimer. The appearance of excimer emission of moderate intensity in presence of H2PO4- distinguishes it from other guests in the present study.

Unravelling the anticancer potency of 1,2,4-triazole-N-arylamide hybrids through inhibition of STAT3: synthesis and in silico mechanistic studies

Abstract: The discovery of potent STAT3 inhibitors has gained noteworthy impetus in the last decade. In line with this trend, considering the proven biological importance of 1,2,4-triazoles, herein, we are reporting the design, synthesis, pharmacokinetic profiles, and in vitro anticancer activity of novel C3-linked 1,2,4-triazole-N-arylamide hybrids and their in silico proposed mechanism of action via inhibition of STAT3. The 1,2,4-triazole scaffold was selected as a privilege ring system that is embedded in core structures of a variety of anticancer drugs which are either in clinical use or still under clinical trials. The designed 1,2,4-triazole derivatives were synthesized by linking the triazole-thione moiety through amide hydrophilic linkers with diverse lipophilic fragments. In silico study to predict cytotoxicity of the new hybrids against different kinds of human cancer cell lines as well as the non-tumor cells was conducted. The multidrug-resistant human breast adenocarcinoma cells (MDA-MB-231) was found most susceptible to the cytotoxic effect of synthesized compounds and hence were selected to evaluate the in vitro anticancer activity. Four of the designed derivatives showed promising cytotoxicity effects against selected cancer cells, among which compound 12 showed the highest potency (IC50 = 3.61?μM), followed by 21 which displayed IC50 value of 3.93?μM. Also, compounds 14 and 23 revealed equipotent activity with the reference cytotoxic agent doxorubicin. To reinforce these observations, the obtained data of in vitro cytotoxicity have been validated in terms of ligand–protein interaction and new compounds were analyzed for ADMET properties to evaluate their potential to build up as good drug candidates. This study led us to identify two novel C3-linked 1,2,4-triazole-N-arylamide hybrids of interesting antiproliferative potentials as probable lead inhibitors of STAT3 with promising pharmacokinetic profiles. Graphic abstract: [Figure not available: see fulltext.]

Design, synthesis and in silico insights of new 7,8-disubstituted-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione derivatives with potent anticancer and multi-kinase inhibitory activities

Aiming to obtain an efficient anti-proliferative activity, structure- and ligand-based drug design approaches were expanded and utilized to design and refine a small compound library. Subsequently, thirty-two 7,8-disubstituted-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione derivatives were selected for synthesis based on the characteristic pharmacophoric features required for PI3K and B-Raf oncogenes inhibition. All the synthesized compounds were evaluated for their in vitro anticancer activity. Compounds 17 and 22c displayed an acceptable potent activity according to the DTP-NCI and were further evaluated in the NCI five doses assay. To validate our design, compounds with the highest mean growth inhibition percent were screened against the target PI3Kα and B-RafV600E to confirm their multi-kinase activity. The tested compounds showed promising multi-kinase activity. Compounds 17 and 22c anticancer effectiveness and multi-kinase activity against PI3Kα and B-RafV600E were consolidated by the inhibition of B-RafWT, EGFR and VEGFR-2 with IC50 in the sub-micromolar range. Further investigations on the most potent compounds 17 and 22c were carried out by studying their safety on normal cell line, in silico profiling and predicted ADME characteristics.

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

Highly Potent and Selective Butyrylcholinesterase Inhibitors for Cognitive Improvement and Neuroprotection

Butyrylcholinesterase (BChE) has been considered as a potential therapeutic target for Alzheimer's disease (AD) because of its compensation capacity to hydrolyze acetylcholine (ACh) and its close association with Aβ deposit. Here, we identified S06-1011 (hBChE IC50 = 16 nM) and S06-1031 (hBChE IC50 = 25 nM) as highly effective and selective BChE inhibitors, which were proved to be safe and long-acting. Candidate compounds exhibited neuroprotective effects and the ability to improve cognition in scopolamine- and Aβ1-42 peptide-induced cognitive deficit models. The best candidate S06-1011 increased the level of ghrelin, a substrate of BChE, which can function as improving the mental mood appetite. The weight gain of the S06-1011-treated group remarkably increased. Hence, BChE inhibition not only plays a protective role against dementia but also exerts a great effect on treating and nursing care.

Synthesis of New Thieno[2,3-d]pyrimidines Containing a 1,2,3-Triazole Ring and Their Therapeutic Response in NCI-60 Cell Line Panel

Abstract: A series of new tetrahydro[1]benzothieno[2,3-d]pyrimidines containing a 1,2,3-triazole fragment linkedthrough an oxymethylene spacer have been synthesized by click reaction of4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidines with various aryl and alkyl azides inthe presence of copper sulfate and sodium ascorbate as a catalyst. Thestructures of the synthesized compounds were characterized by variousspectroscopic techniques (1H and13C NMR, FT-IR, and mass spectrometry), and theirin vitro anticancer activity against NCI-60 human tumor cell lines wasevaluated. Among the compounds tested, N-(pyridine-3-yl)-acetamide derivative exhibited significantactivity against several cancer cell lines, including SF-539 (CNS cancer),HCT-116 (colon cancer), OVCAR-8 (ovarian cancer), PC-3 (prostate cancer), andCCRF-CEM (leukemia).