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Synthesis and application of an antifungal drug and its intermediate
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An antifungal and synthetic method technology, applied in the fields of chemistry and medicine, can solve the problems of reduced sensitivity of antifungal drugs, and achieve good antibacterial effect and low side effects
Active Publication Date: 2019-07-26
广州海博特医药科技有限公司
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[0003] Clinically, antibiotics are mainly used in the treatment of fungal infections. With the widespread use of antibiotics, a variety of drug resistance mechanisms have emerged, which greatly reduces the sensitivity of antifungal drugs.
Method used
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Embodiment 1
[0051] The synthesis of embodiment 1 compound I
[0052] The synthetic route is as follows:
[0053]
[0054] Synthesis reaction: In the reaction flask, add 1.3g of 4-chloro-2-butenamine hydrochloride in 30mL ethanol solution, 1.96g of potassium carbonate, add 0.1g of polyethylene glycol PEG-400 as a phase transfer catalyst, ice After cooling in the bath, a solution of 1g of 1-chloromethylnaphthalene dissolved in 5mL of absolute ethanol was added dropwise with stirring, and the reaction was stirred for 3h. Recover the solvent, add 20 mL of dichloromethane, wash with 10 mL of 10% sodium hydroxide solution and water successively, separate the organic layer, dry over anhydrous sodium sulfate, recover the solvent, and distill under reduced pressure to obtain compound I as (E)-N-(1 -naphthylmethyl)-4-chloro-2-buten-1-amine.
Embodiment 2
[0055] The synthesis of embodiment 2 compound I
[0056] The synthetic route is as follows:
[0057]
[0058] Synthesis reaction: In the reaction bottle, add 1.3g of 4-chloro-2-butenamine hydrochloride in 30mL of methanol solution, 1.72g of triethylamine, 0.1g of polyethylene glycol PEG-400, cool in an ice bath, stir and drop Add 1g of 1-chloromethylnaphthalene dissolved in 5mL of methanol, and stir the reaction for 3.5h. Recover the solvent, add 20 mL of dichloromethane, wash with 10 mL of 5% sodium bicarbonate solution and water successively, separate the organic layer, dry over anhydrous sodium sulfate, recover the solvent, and distill under reduced pressure to obtain compound I as (E)-N-(1 -naphthylmethyl)-4-chloro-2-buten-1-amine.
Embodiment 3
[0059] The synthesis of embodiment 3 compound I
[0060] The synthetic route is as follows:
[0061]
[0062] Synthesis reaction: In the reaction bottle, add 1.3g of 4-chloro-2-butenamine hydrochloride in 40mL of chloroform solution, 0.8g of sodium hydroxide, 0.09g of polyethylene glycol PEG-400, cool in an ice bath, and stir 0.9g of 1-chloromethylnaphthalene solution in absolute ethanol was added dropwise, and the reaction was stirred for 4h. Recover the solvent, add 20 mL of dichloromethane, wash with 10 mL of 33.2% sodium carbonate solution and water successively, separate the organic layer, dry over anhydrous sodium sulfate, recover the solvent, and distill under reduced pressure to obtain compound I as (E)-N-( 1-naphthylmethyl)-4-chloro-2-buten-1-amine.
[0063] The structural characterization data of Compound I obtained in any one of Examples 1 to 3 are:
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Abstract
The invention discloses synthesis and application of a novel anti-fungal medicament and an intermediate thereof, in particular to the synthesis and application of (E)-1-{3-methyl-5-(4-naphthalene methylamine-2-butenyl)-2,4,6-trihydroxy] phenyl}-1-butanone and the intermediate (E)-N-(1-menaphthyl)-4-Halogen-2-butylene-1-amine. Compounds, salts and crystalline hydrate or solvent complexes of the compounds are used for the preparation of antibacterial agents, in particular to antifungal medicament. The bacteriostatic test in vitro shows that the compounds provided have bacteriostatic effect, especially for two skin pathogenic bacteria, Trichophyton rubrum and a gypsum like microspore bacteria, and have very good bacteriostatic effect. The compounds have the advantages of low side effect, antifungal resistance and so on. the compound libraries for the treatment of superficial fungal infection of the skin is enriched, and strong technical support for the preparation of drugs or drug combinations against superficial fungal infections is provided.
Description
technical field [0001] The invention relates to the technical fields of chemistry and medicine, and relates to the synthesis of new compounds and the synthesis method and application of intermediates thereof. Background technique [0002] Dermatophytosis is a superficial fungal infection of the hair, skin and nails caused by dermatophytes, but there are also reports of deep infections caused by it. The common ones clinically are tinea capitis, tinea corporis, jock itch, tinea manuum, tinea pedis and tinea pedis. Occasionally deep tissues may be involved. cause deep infection. Dermatophytes and their metabolites can cause allergic reactions of the skin outside the lesion through blood circulation, which is called ringworm eruption. Dermatophytosis is a group of common diseases and frequently-occurring diseases. It is second to dermatitis and eczema in dermatological outpatient cases, but ranks first in infectious skin diseases. In my country, the number of patients is at...
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