CAS: 218600-53-4; Bardoxolone Methyl

该化合物是一种合成三叶类化合物,产自叶酸,以其强力激活Nrf2途径而著称,该途径规范了细胞抗氧化剂和抗炎反应,在减轻氧化性应激和炎症,特别是慢性肾病(CKD)和肺动脉高血压(PAH)方面表现出有良好的治疗潜力.该化合物调节对红氧化敏感的信号路径的能力强调了其在针对代谢和炎症的临床前科和临床研究中的效用.其药用植物基因特征,包括口服生物利用率,进一步支持其研究用途.巴多克斯酮甲基是处理与氧化性损害和发育调节性炎症相关的病症的重要候选者.

结构式图片

上下游产品

CAS号305818-40-0 Methyl (5ξ,18α)... | CAS号508-02-1 齐墩果酸 | CAS号1724-17-0 齐墩果酸甲酯 | CAS号65023-19-0 Methyl (3α,5ξ,1... | CAS号65023-20-3 (4AS,6AR,6BS,10... | CAS号218600-50-1 3,12-二氧代齐墩果-9(1... | CAS号218600-52-3 (4AS,6AR,6BS,13... | CAS号305818-39-7 Methyl (2E,5ξ,1... | CAS号218600-44-3 2-氰基-3,12-二氧代齐墩...

合成工艺路线路线简述

  • 合成目标产物 Bardoxolone Methyl 主要起始原料 Methanol And Bardoxolone
  • (文献来源)合成步骤主要原料 Methanol 和 Bardoxolone
(4As,6Ar,6Bs,12As,14Ar,14Br)-11-氰基-10-羟基-2,2,6A,置于2,3-二氯-5,6-二氰基-1,4-苯醌体系中,用 苯 用作溶剂,化学反应 0.5H,以92%的收率获得甲基巴多索隆
参考文献:具有修饰的环a和c的合成齐墩果烷和乌烷三萜类化合物:一系列在小鼠巨噬细胞中产生一氧化氮的高活性抑制剂.
标题:具有修饰的环a和c的合成齐墩果烷和乌烷三萜类化合物:一系列在小鼠巨噬细胞中产生一氧化氮的高活性抑制剂.
摘要:我们已经设计和合成了16种新的含有各种修饰的环c的新的齐墩果酸和urs-1-En-3-One三萜类化合物作为潜在的抗炎药和癌症化学预防剂,并评估了它们对小鼠巨噬细胞中γ-干扰素诱导的一氧化氮产生的抑制作用. .该研究表明,与原始的12-烯相比,C环中的9(11)-En-12-One和12-En-11-One官能团的效价提高了约2-10倍.随后,我们设计并合成了a环c-2处具有腈基和羧基且具有9(11)-En-12-One和12-En-C环中具有11个官能团.其中,我们发现,甲基2-氰基-3,12-二氧代油橄榄-1,9(11)-二烯-28-酸酯(25),2-氰基-3,12-Dioxooleana-1,9(11)-Dien-28-Oic Acid(cddo)(26)和甲基2-羧基-3,12-Dioxooleana-1,9(11)-Dien-28-Oate(29)具有极高的效价(ic(50)=
Doi:10.1021/jm0002230

专利信息


专利号:US-10906888-B2
优先权日:2016-07-14
标 题:Pyrimidine carboxamides as inhibitors of Vanin-1 enzyme
发明人:CASIMIRO-GARCIA AGUSTIN; STROHBACH JOSEPH WALTER; HEPWORTH DAVID; LOVERING FRANK ELDRIDGE; CHOI CHULHO; ALLAIS CHRISTOPHE PHILIPPE; WRIGHT STEPHEN WAYNE
权利人:PFIZER
摘要:Compounds, pharmaceutically acceptable salts thereof, are disclosed wherein the compounds have the structure of (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

专利号:US-8067394-B2
优先权日:2006-11-17
标 题:Synthesis and biological activities of new tricyclic-bis-enones (TBEs)
发明人:HONDA TADASHI; SUNDARARAJAN CHITRA; GRIBBLE GORDON W; SPORN MICHAEL B; LIBY KAREN T
权利人:HONDA TADASHI; SUNDARARAJAN CHITRA; GRIBBLE GORDON W; SPORN MICHAEL B; LIBY KAREN T; DARTMOUTH COLLEGE
摘要:This invention describes novel tricyclic-bis-enone derivatives (TBEs), such as TBE-31, TBE-34, TBE-45 and water-soluble TBEs. The methods of preparing these compounds are also disclosed. The inventors demonstrate the ability of these new TBEs to inhibit proliferation of human myeloma cells, inhibit the induction of iNOS in cells stimulated with interferon-γ, induce heme oxygenase-1 (HO-1), induce CD11b expression—a leukemia differentiation marker, inhibit proliferation of leukemia cells, induce apoptosis in human lung cancer, and induce apoptosis in other cancerous cells. The TBEs of this invention are expected to be useful agents for the treatment and prevention of many diseases, including cancer, neurological disorders, inflammation, and pathologies involving oxidative stress.

专利号:US-10308615-B2
优先权日:2015-05-29
标 题:Heterocyclic compounds as inhibitors of Vanin-1 enzyme
发明人:CASIMIRO-GARCIA AGUSTIN; CONDON JEFFREY SCOTT; FLICK ANDREW CHRISTOPHER; GOPALSAMY ARIAMALA; KIRINCICH STEVEN J; MATHIAS JOHN PAUL; STROBACH JOSEPH WALTER; XIANG JASON SHAOYUN; XING LI HUANG; WANG XIAOLUN
权利人:PFIZER
摘要:Compounds, pharmaceutically acceptable salts thereof, are disclosed wherein the compounds have the structure of n nas defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

专利号:CN-108434151-A
优先权日:2008-01-11
标题 :Synthesis of triterpenoids and method for treating diseases

专利号:CN-104739841-B
优先权日:2008-01-11
标题:Synthesis of triterpenoids and method for treating diseases

专利号:US-2018230127-A1
优先权日:2015-08-13
标题 :Bicyclic-Fused Heteroaryl Or Aryl Compounds
发明人:ANDERSON DAVID RANDOLPH; CURRAN KEVIN JOSEPH; GAVRIN LORI KRIM; GOLDBERG JOEL ADAM; LEE ARTHUR; LOWE MICHAEL DENNIS; PATNY AKSHAY; PIERCE BETSY SUSAN; SAIAH EDDINE; TRZUPEK JOHN DAVID
权利人:PFIZER
摘要:Compounds, tautomers and pharmaceutically acceptable salts of the compounds of Formula (Ia) are disclosed which are inhibitors of Interleukin-1 receptor associated kinase (IRAK4). Methods of treatment, methods of synthesis, and intermediates are also disclosed as defined in the specification.
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主要参考文献


1: Hermann C, Lang S, Popp T, Hafner S, Steinritz D, Rump A, Port M, Eder S. Bardoxolone-Methyl (CDDO-Me) Impairs Tumor Growth and Induces Radiosensitization of Oral Squamous Cell Carcinoma Cells. Front Pharmacol. 2021 Jan 29;11:607580. doi: 10.3389/fphar.2020.607580.
2: Yamazaki T, Mimura I, Tanaka T, Nangaku M. Treatment of Diabetic Kidney Disease: Current and Future. Diabetes Metab J. 2021 Jan;45(1):11-26. doi: 10.4093/dmj.2020.0217. Epub 2021 Jan 22.
3: Pedrosa AL, Bitencourt L, Paranhos RM, Leitão CA, Ferreira GC, Simões E Silva AC. Alport Syndrome: a comprehensive review on genetics, pathophysiology, histology, clinical, and therapeutic perspectives. Curr Med Chem. 2021 Jan 7. doi: 10.2174/0929867328666210108113500. Epub ahead of print.

合成参考文献


参考文献:10.1007/s10549-010-0786-2
摘要:Park SK, Sanders BG, Kline K. Tocotrienols induce apoptosis in breast cancer cell lines via an endoplasmic reticulum stress-dependent increase in extrinsic death receptor signaling. Breast Cancer Research and Treatment. 2010 Feb 16;124(2):361–75. doi: 10.1007/s10549-010-0786-2.
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