13293-99-7

Upstream product

• 100-46-9 benzylamine 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 731-90-8 N-(2-hydroxy-1-naphthalidene)aniline 
• 88702-14-1 naphth<1,2-e><1,2,3>-oxathiazine-2,2-dioxide 

Downstream Products

• 64468-27-5 N-Benzyl-3-oxo-3H-naphtho<2,1-b>pyran-2-carboxamid 
• 146733-31-5 bis(N-benzyl-2-hydroxy-1-naphthaldiminato)nickel(II) 
• 139640-69-0 Benzyl-(1,2-dihydro-naphtho[2,1-b]furan-1-yl)-amine 

Relevant academic research and scientific papers

Substituent effects on the ground-state properties of naphthalene-based analogues of salicylideneaniline in solution

Substituent effects on the ground-state properties of seven naphthalene analogues of salicylideneaniline (1-7) were studied by comparison of both steady-state and transient absorption spectra. The naphthalene-based salicylideneanilines 1-5 were prepared from 2-hydroxy-1-naphthaldehyde and corresponding amines. The UV absorption spectra of 1-5 were largely dependent on the substituent group on the amino group. Transient absorption studies revealed that the introduced naphthyl group in 1-5 prolonged the lifetime of 1Ktrans in non-polar solvent probably due to the formation of intramolecular hydrogen bonding between nitrogen and C-H hydrogen on the naphthyl group. In acetonitrile, the lifetimes of 1-6 are much longer than those in benzene, probably because the zwitterionic forms are stabilized in polar solvents, whereas the much shorter lifetime in ethanol suggests that 1Ktrans undergoes the solvent assisted re-enolizaiton reaction in ethanol.

Lipophilicity-antiproliferative activity relationship study leads to the preparation of a ruthenium(II) arene complex with considerable in vitro cytotoxicity against cancer cells and a lower in vivo toxicity in zebrafish embryos than clinically approved cis-platin

Ru(II)-arene complexes are attracting increasing attention due to their considerable antitumoral activity. However, it is difficult to clearly establish a direct relationship between their structure and antiproliferative activity, as substantial structural changes might not only affect their anticancer activity but also tightly control their activation site(s) and/or their biological target(s). Herein, we describe the synthesis and characterization of four ruthenium(II) arene complexes bearing bidentate N,O-donor Schiff-base ligands ([Ru(η6-benzene)(N-O)Cl]) that display a significantly distinct antiproliferative activity against cancer cells, despite their close structural similarity. Furthermore, we suggest there is a link between their respective antiproliferative activity and their lipophilicity, as the latter affects their ability to accumulate into cancer cells. This lipophilicity-cytotoxicity relationship was exploited to design another structurally related ruthenium complex with a much higher antiproliferative activity (IC50 > 25.0 μM) against three different human cancer cell lines. Whereas this complex shows a slightly lower activity than that of clinically approved cis-platin against the same human cancer cell lines, it displays a lower toxicity in zebrafish (Danio rerio) embryos at concentrations up to 20 μM.

Synthesis and Evaluation of a Schiff-Based Fluorescent Chemosensors for the Selective and Sensitive Detection of Cu2+ in Aqueous Media with Fluorescence Off-On Responses

Copper being an essential nutrient; also pose a risk for human health in excessive amount. A simple and convenient method for the detection of trace amount of copper was employed using an optical probe R1 based on Schiff base. The probe was synthesized by Schiff base condensation of benzyl amine and 2-hydroxy-1-napthaldehyde and characterized by single X-ray diffraction, 1H NMR and FTIR. By screening its fluorescence response in a mixture of DMSO and H2O (20:80, v/v) R1 displayed a pronounced enhancement in fluorescence only upon treatment with copper. Other examined metal ions such as alkali, alkaline and transition had no influence. Within a wide pH range 5–12 R1 could selectively detect copper by interrupting ICT mechanism that results in CHEF. From Job’s plot analysis a 2:1 binding stoichiometry was revealed. The fluorescence response was linear in the range 1–10 × 10?9?M with detection limit 30 × 10?9?M. Association constant was determined as 1 × 1011?M?2 by Benesi-Hilderbrand plot. As a fast responsive probe it possesses good reproducibility and was employed for detection of copper in different water samples.

Catalyst-free direct ring-opening of cyclic aldimines with aliphatic primary amines to construct o-hydroxy schiff bases

We firstly describe a catalyst-free direct ring-opening of cyclic aldimines with abundant aliphatic primary amines to construct o-hydroxy schiff bases under mild reaction conditions. The corresponding products were generated in good to excellent yields (80–99%). In addition, a gram-scale reaction and further application of the reaction strategy were performed.

SOLVENT EFFECT IN THE AMINE EXCHANGE OF SCHIFF BASES, II. RELATIONSHIP BETWEEN THE RATE CONSTANT AND THE ACTIVITY COEFFICIENT OF ETHANOL IN ETHANOL-CYCLOHEXANE MIXTURE

The rate of amine exchange has been investigated in the reaction of Schiff bases with primary amines in ethanol-cyclohexane mixtures.The rate constant depends, according to the folowing equation, on the rate constants measured in ethanol and cyclohexanol (k1*, k2*), on the composition of solvent mixture (x1, x2) and on the activity coefficient of ethanol (γ1): log k=x1 logk1* + x2 logk2* + (a+bγ1)x1x2.The validity of the equation is interpreted by the hydrogen bond formed between the ethanol and Schiff base molecules.