N - (((1S, 5R) -6,6-Dimethylbicyclo [3.1.1] hept-2-en-2-yl) methyl) -3-dodecan / tetradecanamido-N N-dimethylpropan-1-aminium Bromide

IF 0.6 Q4 CHEMISTRY, ORGANIC Molbank Pub Date : 2023-07-26 DOI:10.3390/m1704
Liliya E. Nikitina, Ilmir R. Gilfanov, Roman S. Pavelyev, Svetlana A. Lisovskaya, Elena Y. Trizna, Ilfat Z. Rakhmatullin, V. V. Klochkov, Rustam R. Davletshin, Olga B. Babaeva, Alena I. Kolesnikova, Olga V. Ostolopovskaya, Larisa L. Frolova, Airat R. Kayumov
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引用次数: 0

摘要

标题化合物的合成使用月桂酸和肉豆蔻酸进行。使用1H-、13C-NMR和2D 1H-1H COSY、1H-13C HSQC NMR、IR和高分辨率质谱对所获得的化合物进行表征。这两种化合物对金黄色葡萄球菌的杀菌活性与参考药物(米拉米斯汀)相当。与化合物11相比,含有月桂酸片段的化合物10对铜绿假单胞菌的活性高出16倍,而化合物11又含有肉豆蔻酸片段(最小抑制浓度分别为32和512μg/mL)。化合物11对所有类型的真菌都表现出显著的活性(高于米拉米斯汀的活性),而化合物10的活性显著较低。因此,化合物11可以作为治疗各种真菌和葡萄球菌感染的有前途的抗微生物剂,而化合物10对治疗铜绿假单胞菌相关感染感兴趣。
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N-(((1S,5R)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-3-dodecan/tetradecanamido-N,N-dimethylpropan-1-aminium Bromide
The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using 1H-, 13C-NMR and 2D 1H-1H COSY, 1H-13C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds exhibited bactericidal activity on S. aureus comparable to that of a reference drug (miramistin). Compound 10, with lauric acid fragment, had a 16-fold higher activity on P. aeruginosa compared to compound 11, which in turn contains myristic acid fragment (with minimum inhibitory concentrations of 32 and 512 μg/mL, respectively). Compound 11 exhibited a pronounced activity against all types of fungi (higher than the activity of miramistin), while the activity of compound 10 was considerably lower. Thus, compound 11 can serve as a promising antimicrobial agent for the treatment of various fungal and staphylococcal infections, while compound 10 is of interest to treat P. aeruginosa-associated infections.
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来源期刊
Molbank
Molbank Chemistry-Physical and Theoretical Chemistry
CiteScore
0.70
自引率
33.30%
发文量
174
审稿时长
11 weeks
期刊介绍: •organic synthesis •biosynthesis •extraction and purification •natural product derivatives •structural elucidation (X-ray crystallography, NMR, etc.)
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