72724-00-6Relevant articles and documents
Application of gastrodia elata bl derived derivative to preparation of medicine for treating acute or chronic pain
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Paragraph 0094; 0098, (2021/01/20)
The invention discloses application of gastrodia elata bl derived derivatives to preparation of a medicine for treating the acute or chronic pain, in particular to compounds as shown in general formulas (I), (II) and (III) and application of pharmaceutically acceptable salt thereof to preparation of the medicine for preventing and/or treating the acute or chronic pain, discloses a preparation method of the compounds, and belongs to the technical field of medicine.
Application of gastrodia elata bl derived derivatives to preparation of medicine for treating Inflammatory Bowel disease (IBD)
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Paragraph 0052; 0054, (2021/01/20)
The invention discloses compounds as shown in general formulas (I) and (II) and application of pharmaceutically acceptable salt thereof to preparation of a medicine for treating the Inflammatory Boweldisease (IBD), and discloses a preparation method of the compounds.
Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors
Butts, Craig P.,Collingridge, Graham L.,Jane, David E.,Mallah, Shahida,Molnár, Elek,Re?nik, Lisa-Maria,Thatcher, Robert J.,Willis, Christine L.
supporting information, p. 9154 - 9162 (2021/11/16)
(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is
Versatile and Enantioselective Total Synthesis of Naturally Active Gnetulin
Shang, Changhui,Kang, Yulong,Yang, Qingyun,Zhu, Qibin,Yao, Chunsuo
, p. 3768 - 3776 (2019/07/12)
A versatile and efficient enantioselective total synthesis of natural isorhapontigenin dimers (?)-gnetulin, (+)-gnetulin, and (±)-gentulin was proposed. By using this method, we were able to synthesize the dimers from commercial available achiral materials in 13 steps, and achieve a 7%–9% overall yield with >98% enantiomeric excess. The key features of the method include the stereocontrolled enantioselective conjugate reduction of 3-arylindenone catalyzed by methyloxazaborolidine (Me-CBS) and the α-arylation of 3-aryl-1-indanones. Benzylic sulfide was accessed in excellent yield through the InCl3-catalyzed thio-etherification reaction between 2,3-diarylindanol and bezylic thiol. The method is practical and might thus be useful in the enantioselective synthesis of the optical antipodes of natural indane derivatives with or without methoxy groups at aromatic rings. (Figure presented.).
Synthesis of phenolic components of Grains of Paradise
Hattori, Hiroyuki,Mitsunaga,Clive, Derrick L.J.
supporting information, p. 1989 - 1991 (2019/07/03)
Two vanilloids, (5E)-8-(4-hydroxy-3-methoxyphenyl)oct-5-en-4-one (1) and 4-[3-hydroxydecyl]-2-methoxyphenol (2), isolated from the dried seeds of Grains of Paradise (Aframomum melegueta), were synthesized; the latter compound was made as the S-enantiomer and the material derived from the seeds was found to be a 1:1.7 mixture of the R and S isomers. The synthetic route used should allow the preparation of analogs having extended alkyl chains and consequently different lipophilicity, and 3, a homolog of 2, was also prepared.
Synthesis and biological evaluation of novel gigantol derivatives as potential agents in prevention of diabetic cataract
Wu, Jie,Lu, Chuanjun,Li, Xue,Fang, Hua,Wan, Wencheng,Yang, Qiaohong,Sun, Xiaosheng,Wang, Meiling,Hu, Xiaohong,Chen, C.-Y. Oliver,Wei, Xiaoyong
, (2015/12/26)
As a continuation of our efforts directed towards the development of natural anti-diabetic cataract agents, gigantol was isolated from Herba dendrobii and was found to inhibit both aldose reductase (AR) and inducible nitric oxide synthase (iNOS) activity, which play a significant role in the development and progression of diabetic cataracts. To improve its bioefficacy and facilitate use as a therapeutic agent, gigantol (compound 14f) and a series of novel analogs were designed and synthesized. Analogs were formulated to have different substituents on the phenyl ring (compounds 4, 5, 8, 14a-e), substitute the phenyl ring with a larger steric hindrance ring (compounds 10, 17c) or modify the carbon chain (compounds 17a, 17b, 21, 23, 25). All of the analogs were tested for their effect on AR and iNOS activities and on D-galactose-induced apoptosis in cultured human lens epithelial cells. Compounds 5, 10, 14a, 14b, 14d, 14e, 14f, 17b, 17c, 23, and 25 inhibited AR activity, with IC50 values ranging from 5.02 to 288.8 μM. Compounds 5, 10, 14b, and 14f inhibited iNOS activity with IC50 ranging from 432.6 to 1188.7 μM. Compounds 5, 8, 10, 14b, 14f, and 17c protected the cells from D-galactose induced apoptosis with viability ranging from 55.2 to 76.26%. Of gigantol and its analogs, compound 10 showed the greatest bioefficacy and is warranted to be developed as a therapeutic agent for diabetic cataracts.
A short-step asymmetric synthesis of dehydrodiconiferyl alcohol via C-H insertion reaction
Matsumoto, Shogo,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
, p. 1082 - 1084 (2012/06/15)
A rhodium-catalyzed intramolecular C-H insertion reaction using a chiral auxiliary and a chiral catalyst was employed to achieve double asymmetric induction of a trans-disubstituted dihydrobenzofuran ring, as the key reaction of a stereoselective synthesis of (-)-dehydrodiconiferyl alcohol in 13 steps from commercially available guaiacol. Georg Thieme Verlag Stuttgart · New York.
Synthesis and biological activity of pyridopyridazin-6-one p38α MAP kinase inhibitors. Part 2
Tynebor, Robert M.,Chen, Meng-Hsin,Natarajan, Swaminathan R.,O'Neill, Edward A.,Thompson, James E.,Fitzgerald, Catherine E.,O'Keefe, Stephen J.,Doherty, James B.
, p. 5971 - 5975 (2012/11/07)
This manuscript concludes the Structure Activity Relationship (SAR) on the pyridazinone scaffold and identifies a compound with subnanomolar p38α activity and 24 h coverage in the rat arthritis efficacy model.
Total synthesis of (±)-decursivine and (±)-serotobenine: A witkop photocyclization/elimination/O-Michael addition cascade approach
Qin, Hua,Xu, Zhengren,Cui, Yuxin,Jia, Yanxing
, p. 4447 - 4449 (2011/06/22)
A photo op: The concise total syntheses of (±)-decursivine and (±)-serotobenine were achieved by using the titled cascade reaction, which is modeled on the biomimetic pathway. The synthesis of (±)-decursivine, which exhibits antimalarial activity, was carried out in five steps without using protecting groups. Copyright
Synthesis and biological evaluation of isosteric analogs of mandipropamid for the control of oomycete pathogens
Su, Na,Wang, Zhen-Jun,Wang, Li-Zhong,Zhang, Xiao,Dong, Wei-Li,Wang, Hong-Xue,Li, Zheng-Ming,Zhao, Wei-Guang
, p. 101 - 111 (2012/06/01)
A series of isosteric analogs of mandipropamid were designed and synthesized via 'click chemistry'. The amide bond of mandipropamid was substituted by a 1,2,3-triazole functional group. The bioassay results have indicated that some of the title compounds exhibited moderate fungicidal activity against Pseudoperonospora cubensis, and the activity has been systematically studied as a function of molecular structure. The low activity of the mandipropamid analog that contains a lipid chain is likely due to the presence of a weak hydrogen bond donor in the 1,2,3-triazole. Furthermore, we have performed the molecular modeling and found that N-methylamide could be more effective than amide as the surrogates to 1,2,3-triazole, which ultimately leads to a longer distance (1.1A longer) between the two substitutes in the 1,4-disubstituted 1,2,3-triazole compound.
