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首页> 外文期刊>RSC Advances >A greatly improved procedure for the synthesis of an antibiotic-drug candidate 2,4-diacetylphloroglucinol over silica sulphuric acid catalyst: multivariate optimisation and environmental assessment protocol comparison by metrics
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A greatly improved procedure for the synthesis of an antibiotic-drug candidate 2,4-diacetylphloroglucinol over silica sulphuric acid catalyst: multivariate optimisation and environmental assessment protocol comparison by metrics

机译：在二氧化硅硫酸催化剂上合成抗生素 - 药物候选2,4-二乙酰乙酰氯氨酚的大大改善程序：多元优化和度量评估协议由指标进行比较

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Efforts toward the development of a straightforward greener Gram-scale synthesis of the antibiotic compound 2,4-diacetylphloroglucinol ( DAPG ) have been developed. This beneficial procedure was accomplished through the Friedel–Crafts acylation of phloroglucinol over inexpensive heterogeneous silica sulphuric acid ( SSA ) catalyst via ultrasound-assisted (US) synthesis under solvent-free condition. The influences of various parameters such as temperature, catalyst loading, and reaction time on the reaction performance were analysed using a multivariate statistical modelling response surface methodology (RSM). A high yield of DAPG (95%) was achieved at 60 °C after 15–20 min reaction with the presence of 10% (w/w) SSA as the catalyst. Column chromatography-free and a Gram scale-up reaction also exhibited the practical applicability of this newly developed protocol. The SSA catalyst was recovered and recycled up to 10 consecutive runs with no appreciable loss of activity. A plausible mechanism for the Friedel–Crafts acylation of phloroglucinol is proposed. Moreover, an environmental assessment has been carried out over this present method and compared with several established literature using the EATOS software and the Andraos algorithm to assess the consumption of the substrates, solvents, catalysts, and the production of coupled products or by-products. In addition, their energy consumptions were also determined. The data collected showed that the present method is the most promising one, characterised by the highest environmental impact profile against all the other reported methods. The physicochemical properties of the synthesised DAPG were assessed and exhibited reasonable oral bioavailability drug property as determined by Lipinski's rules.
机译：已经开发出努力发展抗生素化合物2,4-二乙酰乙酰氯（DAPG）的直接更环保的革兰氏型合成。通过在无溶剂条件下通过超声辅助（US）合成的富含氟葡聚糖酰氯（SSA）催化剂在溶剂条件下通过超声辅助（US）合成来完成这种有益的程序。使用多元统计建模响应表面方法（RSM）分析了各种参数如温度，催化剂负荷和反应时间对反应性能的影响。在15-20分钟的反应后，在60℃下，在15-20分钟的反应与催化剂存在10％（w / w）SSA的反应后，在60℃下达到高产率。无柱色谱和克拉垢反应也表现出这种新开发的方案的实际适用性。回收SSA催化剂，再循环至多10个连续运行，没有明显的活动丧失。提出了一种可粘性机制的甘黄油酰胺酰化的粘性机制。此外，通过这种方法进行了环境评估，并与使用eatos软件和胸膜算法的几个建立的文献进行了比较，以评估底物，溶剂，催化剂和偶联产品或副产物的生产的消耗。此外，还确定了它们的能量消耗。收集的数据表明，本方法是最有希望的方法，其特征在于对所有其他报告的方法的最高环境影响特征。评估合成DAPG的物理化学性质，并表现出合理的口服生物利用度药物，如Lipinski的规则所确定的。

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