Abstract
Coumarin derivatives are used as fluorescent dyes and medicines. They also have some notable physiological effects, including the acute hepatoxicity and carcinogenicity of certain aflatoxins, the anticoagulant action of dicoumarol, and the antibiotic activity of novobicin and coumerymycin A1. Because the number of drug resistant strains is increasing at present, the synthesis of new antibacterial compounds is one of the critical methods for treating infectious diseases. Therefore, a series of coumarin-substituted derivatives, namely 4-hydroxy- and 7-hydroxycoumarins, and 3-carboxycoumarins were synthesized. 4-Hydroxycoumarin derivatives 4a–c underwent rearrangement reactions. Both 4- and 7-hydroxycoumarins were treated with activated aziridines which produced series of ring-opened products 7, 8, 10, and 11. 3-Carboxy-coumarin amide dimer derivatives 14–21 were prepared by reacting aliphatic alkylamines and alkyldiamines with PyBOP and DIEA. In this study, we use a new technique called modified micro-plate antibiotic susceptibility test method (MMAST), which is more convenient, more efficient, and more accurate than previous methods and only a small amount of the sample is required for the test. Some of the compounds were produced by reactions with acid anhydrides and demonstrated the ability to inhibit Gram-positive microorganisms. The dimer derivatives displayed lower antibacterial activities.
Highlights
Coumarin is a lactone compound which is widely distributed in plants and can be extracted, among others, from Anthoxanthum odoratum, Melilotus officinalis, Dipterix oppositifolia and Dipterix oppositifolia [1]
The final results depend on the substitution of the N-acyl or N-sulfonyl groups on the acyl group, such as benzoyl and the coumarin anions will attack from an abnormal position to provide the major products
It was assumed that compounds [7, 8, 10, 11], and their analogues were formed by the nucleophilic attack of acylaziridines via an SN2-like ring opening mechanism
Summary
Coumarin is a lactone compound which is widely distributed in plants and can be extracted, among others, from Anthoxanthum odoratum, Melilotus officinalis, Dipterix oppositifolia and Dipterix oppositifolia [1]. Various medicinal effects, such as anticoagulant [9,10], analytical fluorescence indicator, anti-inflammatory [11] and antioxidant [12–15] properties have been reported. Many authors have reported the convenient and effective synthesis of the dimers from salicylaldehydes and by biomimetic synthesis. Acetoxycoumarins, polycyclic 7-hydroxycoumarins and other coumarin derivatives display anticarcinogenic properties [16–22]. Roma reported that tricyclic or bicyclic coumarin derivatives with amino groups showed antiplatelet activity [23]. 4-Heteroarylamino-, triazolopyridine, imidazolopyridine, N-substituted-3-carboxamido- and other groups incorporate a coumarin moiety displaying new coumarin derivative structures which showed antibacterial [24–29] and antifungal [30]. Modification of the chemical structure of the coumarin parent skeleton showed unit enzyme inhibition in vitro and in vivo [34–37]. Coumarin combines with sugar units to form C-glycosyl compounds. Microbiological trials using the minimal inhibitory concentration (MIC) on penicillin G, amikin and the new modified micro-plate antibiotic susceptibility test (MMAST) were carried out on different bacterial strains to test the activities of the new compounds [38]
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