52805-48-8

Usage

Synthesis Reference(s)

Tetrahedron, 53, p. 15029, 1997 DOI: 10.1016/S0040-4020(97)01054-5

InChI:InChI=1/C18H14O2/c19-12-17-16-9-5-4-8-15(16)10-11-18(17)20-13-14-6-2-1-3-7-14/h1-12H,13H2

Upstream product

• 100-44-7 benzyl chloride 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 584-08-7 potassium carbonate 

Downstream Products

• 52805-40-0 2-(benzyloxy)naphthalene-1-carbonitrile 
• 93655-27-7 2-(benzyloxy)naphthalene-1-carboxylic acid 
• 167832-87-3 3,5-bis-benzyloxy-4-(2-benzyloxy-naphthalene-1-carbonyl)-benzoic acid 
• 1026442-50-1 3,5-bis-benzyloxy-4-(2-benzyloxy-naphthalene-1-carbonyl)-benzoic acid tert-butyl ester 
• 662160-33-0 2-benzyloxy-1-(2-nitrovinyl)-naphthalene 

Relevant academic research and scientific papers

Acid-base effects, light emission, DNA-binding and photocleavage studies of oligo-homonuclear ruthenium(II) complexes and their computational study

The ground- and excited-state acid ionization constants and the DNA binding properties of mono-, di- and trinuclear ruthenium(II) polypyridine complexes have been studied by electronic absorption and fluorescence emission spectroscopy. The DNA binding abilities of the complexes increase with increasing π-electron multiplicity of phenanthroline groups and the H-bonding properties of imidazole moieties increase from the mononuclear (R1) to dinuclear (R2), followed by trinuclear (R3) complexes. In addition, the increasing surface area of the complexes relatively leads to a corresponding enhancement in binding affinity. The DNA-binding constants, Kb, of the complexes were determined systematically by spectrophotometric titration. In addition to the various ionic interactions, van der Waals interaction, hydrogen bonding, DNA-binding constants Kb and hypochromism of Ru(II) polypyridine complexes inferred the existence of intercalation mode of binding. The trend in DNA-binding affinities as well as the spectral properties of this series of complexes can be reasonably explained by applying the DFT at the B3LYP/LanL2DZ/6-31G level. The results suggest that the multiplication of complex unit has important effects on the electronic structures, a trend in the DNA-binding affinities and an improvement of spectral properties of the complexes. The binding affinity of the ruthenium complexes with biological receptors namely, G-quadraplexes from human telomeres has been investigated. The binding characteristics of complexes have been compared with each other using molecular docking. Further, these complexes tend to promote cleavage of plasmid DNA under photolytic conditions.

Discovery and optimization of selective inhibitors of protein arginine methyltransferase 5 by docking-based virtual screening

Protein arginine methyltransferase 5 (PRMT5) is a type II PRMT enzyme critical for diverse cellular processes and different types of cancers. Many efforts have been made to discover novel scaffold PRMT5 inhibitors. Herein, we report the discovery of DC-P33 as a hit compound of PRMT5 inhibitor, identified by molecular docking based virtual screening and 3H-labeled radioactive methylation assays. Structure-activity relationship (SAR) analysis was performed on the analogs of DC-P33 and then structural modifications were done to improve its activity. Among the derivatives, the compound DC-C01 displayed an IC50 value of 2.8 μM, and good selectivity toward PRMT1, EZH2 and DNMT3A. Moreover, DC-C01 exhibited anti-proliferation activities against Z-138, Maver-1, and Jeko-1 cancer cells with EC50 values of 12 μM, 12 μM, and 10.5 μM, respectively. Taken together, these results contribute to the development of specific inhibitors against PRMT5 and cancer therapy.

Arylthiosemicarbazones as antileishmanial agents

Based on a screening process, we targeted substituted thiosemicarbazone as potential antileishmanial agents. Our objective was to identify the key structural elements contributing to the anti-parasite activity that might be used for development of effective drugs. A series of 32 compounds was synthesized and their efficacy was evaluated against the clinically relevant intracellular amastigotes of Leishmania donovani. From these, 22 compounds showed EC50values below 10?μM with the most active derivative (compound 14) showing an EC50of 0.8?μM with very low toxicity on two different mammalian cell lines. The most relevant structural elements required for higher activity indicate that the presence of a fused bicyclic aromatic ring such as a naphthalene bearing an alkyl or an alkoxy group substituent are prerequisites. Owing to the easy synthesis, high activity and low toxicity, the most active compounds could be considered as a lead for further development.

Hydrazinonaphthalene and azonaphthalene thrombopoietin mimics are nonpeptidyl promoters of megakaryocytopoiesis

High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW 50 values in the region of 1-20 nM.

Thiazoline acid derivatives

Thiazoline acids and derivatives useful as chelators of trivalent metals in therapeutic applications have been prepared.

Synthesis and biological evaluation of naphthyldesferrithiocin iron chelators

The synthesis and iron-clearing properties of the naphthyldesferrithiocins 2-(2'-hydroxynaphth-1'-yl)-Δ2-thiazoline-(4R)-carboxylic acid, 2-(2'- hydroxynaphth-1'-yl)-Δ2-thiazoline-(4S)-carboxylic acid, 2-(3'- hydroxynaphth-2'-yl)-Δ2-thiazoline-(4R)-carboxylic acid, and 2-(3'- hydroxynaphth-2'-yl)-Δ2-thiazoline-(4S)-carboxylic acid are described. While the bile duct-cannulated rat model clearly demonstrates that the 3'- hydroxynaphth-2'-yl compounds are orally active iron-clearing agents and the corresponding 2'-hydroxynaphthyl-1'-yl compounds are not, in the primate model none of the benz-fused desazadesferrithiocin analogues are active. Oral versus subcutaneous administration of these ligands strongly suggests that metabolism is a key issue in their iron-clearing properties and that these benz-fused desferrithiocins are not good candidates for orally active iron- clearing drugs.

4,4'-Binaphthylidene-1,1'-diones - Colour and Structure

Synthesis and properties of various 4,4'-binaphthylidene-1,1'-diones are described.The UV spectra of the deep red to purple diones may be calculated on the base of substituent increments.The experimental values of the analyzed substituents can be reproduced using PPP calculations with satisfying accuracy, which makes it possible to predict also absorption maxima of hitherto unknown 4,4'-binaphthylidene-1,1'-diones.Keywords: 4,4'-Binaphthylidene-1,1'-diones, Phenol Oxidation

Hypoglycemic 5-substituted oxazolidine-2,4-diones

Hypoglycemic 5-phenyl and 5-naphthyl oxazolidine-2,4-diones and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.