Bulk Raw Materials butenafine Powder

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butenafine Powder Usage and Synthesis.

Butenafine can inhibit squalene cyclooxygenase activity at low concentrations, resulting in squalene accumulation and insufficient ergosterol synthesis in fungi:

(1) Squalene has a direct toxic effect on fungal cells, which can lead to the rapid death of fungi, showing the fungicidal activity of Butenafine;

(2) Ergosterol is an essential component for the formation of fungal cell membranes. Insufficient synthesis of ergosterol inhibits fungal growth. Insufficient synthesis of ergosterol inhibits the growth of fungi. This dual action of Butenafine causes rupture of the fungal cell membrane, which demonstrates its potent fungicidal activity. Butenafine also has a direct destructive effect on fungal cell membranes at higher concentrations.

Unlike azoles, Butenafine does not inhibit cytochrome P450 enzymes and does not affect adrenal and gonadal hormone synthesis.

The main mechanism is that Butenafine has a direct destructive effect on the cell membrane of Candida albicans; at the same time, the inhibition of fungal ergosterol synthesis by Butenafine makes the fungal cell membrane more sensitive to the direct destructive effect of Butenafine.

In addition, human trials have demonstrated that Butenafine has prominent anti-inflammatory activity, eliminating erythema of the skin due to medium-wave ultraviolet irradiation. Naftifine also had strong anti-inflammatory effects, whereas terbinafine did not.

Uses and functions of butenafine.

Butenafine is mainly used for the topical treatment of tinea pedis, tinea corporis and tinea cruris caused by tinea corporis, tinea rossi, tinea pedis and tinea versicolor.

Pharmacological Effects of butenafine.

Butenafine is a benzylamine derivative, its mechanism of action is to selectively inhibit the fungal squalene epoxidase, interfere with the biosynthesis of ergosterol in the fungal cell wall, affecting the lipid metabolism of the fungus, so that the fungal cells are damaged or dead to play a bactericidal and bacteriostatic effect.

Production method of butenafine Powder.

1. Take 1-naphthalenecarboxylic acid as raw material, get 1-naphthalenecarbonyl chloride by sulfoxide chloride, condense with 1-(4-tert-butylbenzene)-N-methylmethylamine to get N-(4-tert-butylbenzyl)-N-methyl-1-naphthalenecarboxamide, and then reduce by lithium aluminium hydroxide, form salt, and then make Butylnaphthalenefen Hydrochloride.

2. P-tert-butyl benzoic acid as raw material, p-tert-butylbenzoyl chloride is obtained by chlorination with sulfoxide, 4-tert-butyl-N-methyl-N-(methylnaphthalene) benzamide is obtained by condensation with N-methylnaphthalene methanamine, and then BUTYLNAFEN HYDROCHLORIDE is obtained by reduction and formation of salt by lithium aluminium hydride.

3. 1-chloromethyl naphthalene was synthesised by chloromethylation using naphthalene as raw material, and then N-methyl naphthalene methylamine was generated by reaction with methylamine, and then condensed with p-tert-butylbenzyl chloride to form salt, to obtain Butenafine hydrochloride.

4. Take naphthalene as the starting material, and produce 1-chloromethyl naphthalene by chloromethylation reaction, then replace it with methylamine to get the key intermediate N-methyl-1-naphthalene methylamine hydrochloride, then condense it with 4-tert-butylbenzyl chloride, and then get Butenafine Hydrochloride by salt formation and recrystallisation.

5. N-methyl-1-naphthalene methylamine hydrochloride (2) (41.5g, 0.20mol) was added to the mixture of toluene (150ml) and 10% sodium hydroxide solution (160g), heated to 80 ℃, stirring dropwise addition of p-tert-butylbenzyl chloride (3) (40.2g, 0.22mol), about 1h drop, continue to stir the reaction for 3h. Stop the reaction, cooled to room temperature. The reaction was stopped, cooled to room temperature and the organic layer was separated, washed with water to neutral and dried with anhydrous sodium sulfate.

Filtering, recovery of toluene, add appropriate amount of ethanol to dissolve the residue, with concentrated hydrochloric acid to pH 2, solvent recovery to white 1 crude (59.8g). Recrystallised from 50% ethanol to obtain white pure product 1.

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