CAS: 32492-74-3; 14,26-Dihydroxy-15,16-Dimethoxy-1,2(1,3)-Dibenzenacyclononaphan-5-One

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dibenzylmyricanone Myricanol (+)-S-myricanol 5-O-β-D-glucopyranoside 1-(4-benzyloxyphenyl)-7-(2-benzyloxy-5-bromo-3,4-dimethoxyphenyl)heptan-3-ol(+/-)-myricanol

📜在 (1,1'-Bis(Diphenylphosphino)Ferrocene)Palladium(II) Dichloride,Palladium On Activated Charcoal,氢气,Potassium Acetate,对甲苯磺酸,溶剂黄146体系中,用 二甲基亚砜,乙腈 用作溶剂,化学反应生成杨梅酮
参考文献:Synthesis,Stereochemical Analysis,And Derivatization Of Myricanol Provide New Probes That Promote Autophagic Tau Clearance
标题:Synthesis,Stereochemical Analysis,And Derivatization Of Myricanol Provide New Probes That Promote Autophagic Tau Clearance
摘要:We Previously Discovered That One Specific Scalemic Preparation Of Myricanol (1),A Constituent Of Myrica Cerifera (Bayberry/southern Wax Myrtle) Root Bark,Could Lower The Levels Of The Microtubule-Associated Protein Tau (Mapt). The Significance Is That Tau Accumulates In A Number Of Neurodegenerative Diseases,The Most Common Being Alzheimers Disease (Ad). Herein,A New Synthetic Route To Prepare Myricanol Using A Suitable Boronic Acid Pinacol Ester Intermediate Is Reported. An X-Ray Crystal Structure Of The Isolated Myricanol (1) Was Obtained And Showed A Co-Crystal Consisting Of (+)-Ar,11S-Myricanol (2) And (-)-As,11R-Myricanol (3) Coformers. Surprisingly,3,Obtained From Chiral Separation From 1,Reduced Tau Levels In Both Cultured Cells And Ex Vivo Brain Slices From A Mouse Model Of Tauopathy At Reasonable Mid-To-Low Micromolar Potency,Whereas 2 Did Not. Silac Proteomics And Cell Assays Revealed That 3 Promoted Tau Degradation Through An Autophagic Mechanism,Which Was In Contrast To That Of Other Tau-Lowering Compounds Previously Identified By Our Group. During The Course Of Structureactivity Relationship (Sar) Development,We Prepared Compound 13 By Acid-Catalyzed Dehydration Of 1. 13 Had Undergone An Unexpected Structural Rearrangement Through The Isomyricanol Substitution Pattern (E.G.,16),As Verified By X-Ray Structural Analysis. Compound 13 Displayed Robust Tau-Lowering Activity,And,Importantly,Its Enantiomers Reduced Tau Levels Similarly. Therefore,The Semisynthetic Analogue 13 Provides A Foundation For Further Development As A Tau-Lowering Agent Without Its Sar Being Based On Chirality.
Doi:10.1021/cb501013W