65473-08-7

Usage

Class

Naphthalene derivatives

Type of compound

Organic compound, Chiral amine

Uses

Building block in the synthesis of pharmaceutical compounds and agrochemicals

Structure

Naphthalene ring, methyl group, phenyl-2-propenyl group

Reactivity

Structure affects its reactivity in chemical reactions

Biological activity

Structure contributes to its biological activity

(Z)-Configuration

Indicates the geometrical orientation of the double bond in the molecule, affecting its properties and interactions in chemical reactions.

Upstream product

• 86-52-2 1-Chloromethylnaphthalene 
• 14489-75-9 N-methyl-1-naphthalenemethylamine 
• 98977-91-4 N-methyl-N-(3-phenyl-2-propynyl)-1-naphthalenemethanamine 

Relevant academic research and scientific papers

The photostability of antimycotics. 3. Photostability of locally acting antimycotics

The photochemical stability of a number of topical antimycotic drugs was tested. The light sensitivity decreases in the order naftifine, sulbentine, cloxiquin, tolnaftate and chlorphenesin. A liquid chromatography-mass spectrometry system was used to identify a number of photodegradation products. Light exposure of sulbentine leads to the formation of benzylisothiocyanate. Chlorphenesine solutions undergo photodehalogenation with the formation of varying photodegradation products depending on the solvent used. The photochemical reactions of naftifine are a cis-trans-isomerization and the formation of a dimer product. Drug preparations are also degraded under light exposure in a simulated topical application. Excipients in the drug preparations strongly influence the photodegradation kinetics and the chemical structure of photodegradation products.

Synthesis and Structure-Activity Relationships of Naftifine-Related Allylamine Antimycotics

Naftifine (1) is the first representative of the new antifungal allylamine derivatives.Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals.A tertiary allylamine function seems to be a prerequisite for activity against fungi.By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations.Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.