7508-18-1

Usage

Class

Acetic acids

Role in Body

Important mediator of inflammation

Involvement

Immune response, allergic reactions, blood clot formation

Function

Potent chemoattractant for neutrophils (white blood cells)

Significance

Potential target for drug development to treat inflammatory conditions

Structure

Derived from acetic acid with a naphthalene ring fused to a cyclohexane ring

Molecular Weight

284.35 g/mol

Appearance

Crystalline solid

Solubility

Soluble in organic solvents, such as ethanol and methanol

Stability

Stable under normal conditions, but sensitive to light and heat

Biological Activity

Acts as a potent chemoattractant for neutrophils, promoting their migration to sites of inflammation

Medical Applications

Research focus for developing drugs to treat inflammatory conditions, such as asthma, arthritis, and inflammatory bowel disease

Synthesis

Can be synthesized through various chemical reactions, often involving the coupling of naphthalene derivatives with acetic acid derivatives

Detection

Typically identified and quantified using techniques such as high-performance liquid chromatography (HPLC) or mass spectrometry (MS)

InChI:InChI=1/C14H12O2/c15-13(16)8-11-7-10-5-1-3-9-4-2-6-12(11)14(9)10/h1-6,11H,7-8H2,(H,15,16)

Upstream product

• 103457-82-5 ethyl 2-(1,2-dihydroacenaphthylen-1-yl)acetate 
• 2235-15-6 1(2H)-acenaphthylenone 
• 231949-34-1 Ethyl₂-(1,2-dihydro-1-acenaphthylenylidene)acetate 

Downstream Products

• 130800-19-0 2-Acenaphthen-1-ylmethyl-cyclohexanone 

Relevant academic research and scientific papers

Tricyclic compounds, preparation method and pharmaceutical compositions containing same

The invention concerns compounds of formula (I) in which: A forms a tricyclic system of formula A1, A2, A3or A4; R1represents a hydrogen atom, an alkyl, hydroxy, alkoxy or oxo group; (R2)mand (R3)m′are such as defined in the description; n represents an integer such that 0≦n≦3; p represents an integer such as defined in the description; B represents a group (a) or (b). The invention is useful for preparing medicines.

Synthesis of phenalene and acenaphthene derivatives as new conformationally restricted ligands for melatonin receptors

Conformationally restricted phenalene and acenaphthene derivatives 5 were synthesized from phenalen-1-one and acenaphthen-1-one derivatives using the Horner-Emmons reaction. The amines were prepared through the corresponding isocyanates by the Curtius reaction on the acids or by the reduction of the nitriles. Amido derivatives (R3 = Me, Et, n-Pr, c-Pr) were prepared by acylation of the amines with the appropriate anhydrides or acid chlorides or by the reductive acylation of the nitriles. The affinities of the compounds for melatonin binding sites were evaluated in vitro in binding assays using chicken brain melatonin and the human mt1 and MT2 receptors expressed in HEK-293 cells. The functionality of the compounds was determined by the potency to lighten the skin of Xenopus laevis tadpoles. Highly potent compounds were obtained. The data highlighted the role of the methoxy group located in the ortho position to the ethylamido chain as compounds with picomolar affinities such as 14c were obtained (chicken brain, hmt1, hMT2 K(i) values = 0.02, 0.008, 0.069 nM, respectively). Compound 14c was equipotent to the corresponding dimethoxy derivative 15c (chicken brain, hmt1, hMT2 K(i) values = 0.07, 0.016, 0.1 nM, respectively). On the other hand, the restricted conformation of the amido chain did not influence selectivity for the cloned hmt1 and hMT2 receptors. These compounds were also potent agonists of melanophore aggregation in X. laevis. 15a,c were several hundred fold more potent than melatonin (EC50 = 0.025, 0.004 nM, respectively). Conformational studies indicated that the minimum energy folded conformation of the ethylamido chain could constitute the putative active form in the receptor site in agreement with previous results.