94-33-7Relevant articles and documents
Kinetic Modeling of Ethylene Glycol Monoesterification
Pe?ar, Darja,Gor?ek, Andreja
, p. 658 - 663 (2015)
The monoesterification of ethylene glycol under isothermal conditions was conducted using benzoic acid in methane-sulfonic acid/Al2O3 as a catalyst. Using this reagent, glycol was selectively monoesterified with high yield. The reactions were performed within an automated batch reactor under equimolar conditions, constant rotational frequency of the stirrer, and within the temperature range from 65 to 85°C. The rate constant related to this reaction and to the corresponding reverse reaction, activation energy, and preexponential factor was derived from experimental data. It has been concluded that under these conditions the formation of dibenzoate was successfully prevented.
Expanding the Tool Kit of Automated Flow Synthesis: Development of In-line Flash Chromatography Purification
Thomson, Christopher G.,Banks, Colin,Allen, Mark,Barker, Graeme,Coxon, Christopher R.,Lee, Ai-Lan,Vilela, Filipe
supporting information, p. 14079 - 14094 (2021/07/31)
Recent advancements in in-line extraction and purification technology have enabled complex multistep synthesis in continuous flow reactor systems. However, for the large scope of chemical reactions that yield mixtures of products or residual starting materials, off-line purification is still required to isolate the desired compound. We present the in-line integration of a commercial automated flash chromatography system with a flow reactor for the continuous synthesis and isolation of product(s). A proof-of-principle study was performed to validate the system and test the durability of the column cartridges, performing an automated sequence of 100 runs over 2 days. Three diverse reaction systems that highlight the advantages of flow synthesis were successfully applied with in-line normal- or reversed-phase flash chromatography, continuously isolating products with 97-99% purity. Productivity of up to 9.9 mmol/h was achieved, isolating gram quantities of pure product from a feed of crude reaction mixture. Herein, we describe the development and optimization of the systems and suggest guidelines for selecting reactions well suited to in-line flash chromatography.
Design and synthesis of tricyclic terpenoid derivatives as novel PTP1B inhibitors with improved pharmacological property and in vivo antihyperglycaemic efficacy
Chen, Feng,Chen, Jiabao,Gao, Cheng,Li, Junyan,Liu, Siyan,Qian, Shan,Wang, Zhouyu,Yang, Lingling,Zhang, Yuanyuan
, p. 152 - 164 (2019/11/25)
Overexpression of protein tyrosine phosphatase 1B (PTP1B) induces insulin resistance in various basic and clinical research. In our previous work, a synthetic oleanolic acid (OA) derivative C10a with PTP1B inhibitory activity has been reported. However, C10a has some pharmacological defects and cytotoxicity. Herein, a structure-based drug design approach was used based on the structure of C10a to elaborate the smaller tricyclic core. A series of tricyclic derivatives were synthesised and the compounds 15, 28 and 34 exhibited the most PTP1B enzymatic inhibitory potency. In the insulin-resistant human hepatoma HepG2 cells, compound 25 with the moderate PTP1B inhibition and preferable pharmaceutical properties can significantly increase insulin-stimulated glucose uptake and showed the insulin resistance ameliorating effect. Moreover, 25 showed the improved in vivo antihyperglycaemic potential in the nicotinamide–streptozotocin-induced T2D. Our study demonstrated that these tricyclic derivatives with improved molecular architectures and antihyperglycaemic activity could be developed in the treatment of T2D.
