666-84-2Relevant academic research and scientific papers
Behaviour of terpene peroxides from abietic acid in the presence of heme and non-heme iron(II)
Muellner, Ursula,Huefner, Antje,Haslinger, Ernst
, p. 3893 - 3899 (2000)
In aqueous acetonitrile with FeCl2 or hemin/L-cysteine, a peroxide (4) obtained from abietic acid by photosensitized air oxidation undergoes rearrangement to give a diepoxide and two spiro compounds as major products. (C) 2000 Elsevier Science Ltd.
In vitro anti-inflammatory activity of larch (Larix decidua L.) sawdust
Pferschy-Wenzig, Eva M.,Kunert, Olaf,Presser, Armin,Bauer, Rudolf
, p. 11688 - 11693 (2008)
The influence of larch (Larix decidua L.) sawdust extracts on arachidonate metabolism has been evaluated in vitro. Extracts of different polarities were tested for their ability to inhibit prostaglandin formation by COX-1 and COX-2 and LTB4 formation by 5-LOX. The lipophilic n-heptane extract showed the highest activity (IC50 values: COX-1, 5 μg/mL; COX-2, 0.1 μg/mL; LTB4 assay, 11.1 μg/mL). A series of abietane, pimarane, and labdane type diterpenes isolated from this extract turned out to be potent inhibitors of LTB4 product formation, whereas their COX inhibitory activity was less pronounced. From the abietane type diterpenes, compounds possessing a 7,13-abietadiene skeleton were better inhibitors of LTB4 formation than those with an 8,11,13-abietatriene skeleton. Compounds bearing an OH group in position 4 were more active than those substituted with a COOH group, and methylation of the COOH group led to an almost complete loss of LTB4 formation inhibitory activity.
Sulfonium sulfonate photoacid generator synthesized from abietic acid and synthesis method of sulfonium sulfonate photoacid generator
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Paragraph 0045-0047, (2021/04/14)
The invention discloses a sulfonium sulfonate photoacid generator synthesized from abietic acid, and relates to the field of photoacid generators. The sulfonium sulfonate photoacid generator has a structural formula shown in the specification, in the formula, R1 is an oxygen-containing linking group, and R2 is a fluoroalkyl group. The photoacid generator can reduce the diffusion of the photoacid generator, improve the edge roughness, reduce the line width roughness and improve the resolution; the photoacid generator is more transparent under 193 nm, and exposure under a 193 nm light source is facilitated; the etching resistance is excellent; the photoacid generator is balanced in hydrophilicity and lipophilicity, has proper adhesive force and excellent solubility, is more uniform in dissolution, and is simple in synthetic route.
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.
Total Synthesis of Nominal ent-Chlorabietol B
Guan, Xingchao,Li, Yulong,Xie, Zhipeng,Xie, Zhixiang,Xu, Zhezhe
, p. 5724 - 5732 (2020/05/19)
The nominal enantiomer of chlorabietol B was regio- and stereoselectively synthesized from (-)-abietic acid in 13 steps. Key features of the synthesis involved an oxidative [3+2] cycloaddition to install the dihydrobenzofuran moiety and an Aldol reaction, followed by elimination and reduction steps to introduce the long chain with three cis double bonds. However, obvious differences in the NMR spectra of the synthetic and natural samples suggested that the proposed structure of chlorabietol B should be revised carefully.
A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water
Yang, Yunqin,Meng, Xiangtai,Zhu, Baolong,Jia, Ying,Cao, Xiaoji,Huang, Shenlin
supporting information, p. 1166 - 1169 (2019/01/04)
Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.
Late-stage C-H amination of abietane diterpenoids
Lapuh, María Ivana,Dana, Alejandro,Di Chenna, Pablo H.,Darses, Benjamin,Durán, Fernando J.,Dauban, Philippe
supporting information, p. 4736 - 4746 (2019/05/24)
This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C-H amination reactions using iodine(iii) oxidants for the late-stage functionalization of natural products. Inter-and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo-and stereoselectivities.
Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
Ong, Derek Yiren,Yen, Zhihao,Yoshii, Asami,Revillo Imbernon, Julia,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 4992 - 4997 (2019/03/13)
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.
Preparation method of 15-hydroxyl dehydrogenated abietane and intermediate of 15-hydroxyl dehydrogenated abietane
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Paragraph 0072-0075; 0077, (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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Paragraph 0078; 0079; 0081, (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)
