24563-96-0

Upstream product

• 666-84-2 abietinol 
• 98-59-9 p-toluenesulfonyl chloride 
• 514-10-3 abietic acid 
• 127-25-3 methyl abietate 
• 631-71-0 ethyl abietate 

Downstream Products

• 666-84-2 abietinol 
• 3772-55-2 dehydroabietinol 

Relevant 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

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.

Rosin acid derivatives

The invention belongs to the technical field of chemical pharmacy, and particularly discloses a preparation method for an abietic acid derivative. Abietic acid 1 is dissolved in solvent, alkali is added, halogenated hydrocarbon is added, and then an intermediate 2 is obtained; the intermediate 2 is dissolved in solvent, lithium aluminum hydride is added, the pH is regulated to 6 through diluted hydrochloric acid, and then an intermediate 3 is obtained; the intermediate 3 is dissolved in solvent, paratoluensulfonyl chloride is added, and then an intermediate 4 is obtained; the intermediate 4 is dissolved in solvent, NaI and Zn are added, and then an intermediate 5 is obtained; the intermediate 5 is dissolved in solvent, hydrogen bromide is added, washing is performed through frozen glacial acetic acid, and then an intermediate 6 is obtained; the intermediate 6 is dissolved in solvent, alkali is added, diluted hydrochloric acid is added to regulate the PH to 2-3, and then an intermediate 7 is obtained; the intermediate 7 is dissolved in solvent, selenium dioxide is added, and a product 8 is obtained. According to the preparation method of the abietic acid derivative, the yield is high; particularly, Huang-Minlon reduction reaction needing high temperature is avoided, so that the requirement for reaction conditions is low; in addition, the product purity is greatly improved.

Preparation method of 15-hydroxyl dehydrogenated abietane and intermediate of 15-hydroxyl dehydrogenated abietane

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)

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)

Synthesis of (+)-amberketal and its analog from l-abietic acid

(+)-Amberketal (1) and its analog (2) have been synthesized from commercially available l-abietic acid (3) by a selective reduction of an unsaturated aldehyde in the presence of a ketone and simultaneous reduction of an iodide using an aqueous suspension of Raney Ni as the key step.

Synthesis and characterization of abietadiene, levopimaradiene, palustradiene, and neoabietadiene: Hydrocarbon precursors of the abietane diterpene resin acids

The abietane diterpenes - abietadiene, levopimaradiene, palustradiene, and neoabietadiene (1b-4b) - were prepared from the corresponding resin acids by diazomethane esterifications, LiAlH4 reductions, tosylations, and Zn/NaI reductions. Abietadiene was also obtained less efficiently by catechol borane reduction of abietadienal tosylhydrazone and Li/NH3 reduction of its 18-phenylthio derivative. These conjugated dienes were characterized by chromatographic properties (HPLC, TLC, GC), MS fragmentation patterns, optical rotations, and UV, IR, 1H NMR, and 13C NMR data. Assignments for the 1H and 13C NMR spectra were made by COSY, DEPT, HMQC, HMBC, NOE data, H-H coupling analysis, and comparisons with literature data. The four diterpenes were identified as cyclization products of recombinant abietadiene synthase, supporting their likely role in the biosynthesis of the abietane resin acids in conifer oleoresin.

Conversion of Abietic Acid into Analogues of Ambergris Odorants

The conversion of methyl abietate (16) into (42) and (43), analogues of the known amber odorants (1) and (2), is reported.