65894-41-9Relevant academic research and scientific papers
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.
Preparation method of 15-hydroxyl dehydrogenated abietane and intermediate of 15-hydroxyl dehydrogenated abietane
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, (2017/08/29)
The invention discloses a preparation method of 15-hydroxyl dehydrogenated abietane and an intermediate of 15-hydroxyl dehydrogenated abietane. The preparation method comprises the following steps: converting a compound 1 into a compound 5, and converting the compound 5 into a compound 8. According to the method for preparing the compound 8, the problem that a product cannot be separated out of a glacial acetic acid solution because reaction impurities are remarkably increased when the feeding quantity is increased at the hydrogen bromide addition step in the existing synthesis route is solved through continuous screening of a process route. Furthermore, the method provided by the invention is high in yield at each step, easy to amplify and suitable for industrialized large-scale production. (The formula is as shown in the description.).
8. 11, 13 - Lohans Pinaceae - 13 - ol and intermediate preparation method (by machine translation)
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, (2017/08/30)
The present invention discloses a process for preparing compound 9 shown 8, 11, 13 - Lohans Pinaceae - 13 - alcohol, or its pharmaceutically acceptable salt, or its solvate of the method, the method comprises the following steps: h, in the presence of oxidizing agent and acid, in order to compound 8 as raw material preparation to obtain compound 9; wherein oxidizing agent selected from hydrogen peroxide or over-tertiary butyl alcohol, acid selected from H2 SO4 , Toluenesulfonates. Process for making a compound of the present invention 9 of the method, the method is simple, high yield, easy to enlarge, and is suitable for industrial large-scale production. (by machine translation)
New route to 15-hydroxydehydroabietic acid derivatives: Application to the first synthesis of some bioactive abietane and nor-abietane type terpenoids
Alvarez-Manzaneda,Chahboun,Guardia,Lachkar,Dahdouh,Lara,Messouri
, p. 2577 - 2580 (2007/10/03)
A new route to 15-hydroxydehydroabietic acid derivatives from abietic acid (11), via abieta-8,13(15)-dien-18-oic acid (12), is reported. Utilizing this, the first synthesis of bioactive terpenes 3, 6, 9 and 10, as well as natural diol 4 and lactones 7-8 was achieved.
