光学活性5-羟基和5-乙酰氧基烷乙酰胺类似物的合成、抑菌活性和香水缓释性能

IF 1.3 3区化学 Q3 CHEMISTRY, ORGANIC

Heterocyclic Communications Pub Date : 2020-01-01 DOI:10.1515/hc-2019-0103

Yasutaka Shimotori, M. Hoshi, N. Ogawa, T. Miyakoshi, T. Kanamoto

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引用次数: 2

摘要

摘要5-乙酰氧基和5-羟基烷硫酰胺类似物对金黄色葡萄球菌具有较高的抗菌活性。以5-烷基-δ-内酯为原料，经酰胺化、硫代化和脱乙酰化反应制备了抗菌硫代酰胺。以Cbz-L-脯氨酸为拆分剂，通过非对映体拆分制备了具有99%非对映过量的光学活性硫代酰胺。用脂肪酶催化剂对抗菌硫代酰胺进行缓慢的内酯化反应。因此，这些硫代酰胺是具有抗菌性能的潜在的缓释香料化合物。

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Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- and 5-acetoxyalkanethioamide analogues

Abstract 5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. Therefore, these thioamides are potential sustained-release perfume compounds having antibacterial properties.

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来源期刊

Heterocyclic Communications 化学-有机化学

CiteScore

3.80

自引率

4.30%

发文量

审稿时长

1.4 months

期刊介绍： Heterocyclic Communications (HC) is a bimonthly, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.