CAS: 118525-40-9; 3,5,7-Trihydroxy-2-(4-Methoxyphenyl)-8-(3-Methylbut-2-En-1-yl)-4H-Chromen-4-One

该化合物是一种氟芳烃化合物,其特点是其铬骨质,这是许多天然产品中常见的结构模型.该化合物具有多种氢氧基组的特点,有助于其潜在的抗氧化性特性,以及一种可加强其生物活动的甲基苯基替代体.存在一个丙基基侧链(3-甲基-丁-2-en-1-yl)表明有可能与生物目标发生再活动并发生互动.这种氟芳烃经常研究其药理效应,包括抗食气,抗微生物学和抗癌活动.该化合物中功能组的具体安排可能会影响其溶性,稳定性以及与酶或感应体的相互作用.

结构式图片

上下游产品

sagittatoside A icariin 2)α-L-rhamnopyranoside-7-O-β-D-glucopyranoside4'-methoxy-5-hydroxy-8-3,3-dimethylallylflavone 3-O-β-D-glucopyranosyl(1*2)α-L-rhamnopyranoside-7-O-β-D-glucopyranoside 4-methoxybenzoic acid2,3,4,5,6-pentahydroxy-hexanal 8-prenylkaempferol 3,7-dimethanesulfonyl-8-prenyl-4'-methoxychrysin

合成工艺路线路线简述

  • 合成目标产物 Icaritin 主要起始原料 Baohuoside I
  • (文献来源)合成步骤主要原料 Baohuoside I
在 Glucosidase体系中,化学反应 1.0H,反应生成去水淫羊藿黄素
参考文献:一种淫羊藿的磷酸酯类衍生物及其制备方法和应用
标题:一种淫羊藿的磷酸酯类衍生物及其制备方法和应用
摘要:本发明属于药物技术领域,公开了一种淫羊藿的磷酸酯类衍生物及其制备方法和应用.所述的淫羊藿的磷酸酯类衍生物的化学结构式如式(1)所示,其中,R1选自或r2选自h或r1,R3选自h或本发明的淫羊藿的磷酸酯类衍生物,部分修饰后衍生物较修饰前细胞毒性显著增强,同时在抗骨质疏松.该淫羊藿的磷酸酯类衍生物可应用在制备前列腺癌细胞的药物,抗骨质疏松的保健品,药物辅料或药品领域中.

海关参考信息

专利信息


专利号:WO-2022116382-A1
优先权日:2020-12-04
标题 :Human glucagon-like peptide-1 receptor activator and application thereof
发明人:LI YINXIONG; XIONG YUE; FANG JI
权利人:GUANGZHOU INST BIOMED & HEALTH
摘要:A human glucagon-like peptide-1 receptor (GLP-1R) activator, comprising a compound of formula I or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, and R6 are each independently selected from any one of H, C1-C4 alkyl, mercapto, phosphate, vinyl, or acetyl. The compound of formula I or the pharmaceutically acceptable salt thereof can improve glycolipid metabolism of the tissue cells of a whole body, enhance the oxidative degradation of lipid molecules, inhibit the expression of lipogenic genes, inhibit the activity of acetyl coenzyme A synthetases, reduce the synthesis of triglyceride, improve the synthesis and secretion of glucose-induced insulin, relieve insulin antagonism, relieve the compensatory amplification of pancreatic islets β cells, and improve the survival rate and function of a pancreatic cell in a type-II diabetes sample state.

专利号:CN-115353522-A
优先权日:2022-08-22
标 题:Regioselective Synthesis of Icaritin-Norcantharidin Conjugate and Its Antitumor Application

专利号:CN-120005740-A
优先权日:2023-11-14
标题:Recombinant microorganism for high-level synthesis of polyphenol compounds and application thereof

专利号:CN-115181112-A
优先权日:2022-08-19
标 题 :Synthesis of 6-bromocyclo-icaritin chromane 3, 4-diketone derivative and anti-tumor application thereof

专利号:CN-115353522-B
优先权日:2022-08-22
标 题 :Regioselective Synthesis of Icaritin-Norcantharidin Conjugate and Its Antitumor Application

专利号:WO-2025082260-A1
优先权日:2023-10-17
标题:Icaritin carbamate prodrug, and preparation method therefor and use thereof
发明人:JIANG QIKUN; ZHANG TIANHONG; LI FENGXIAO; WANG WEIPING; FAN JIAQI; Zhai Yixiu
权利人:UNIV SHENYANG PHARMACEUTICAL
摘要:Provided are a preparation method for and the use of an icaritin carbamate prodrug and a salt thereof, which belong to the pharmaceutical field. In particular, provided are an icaritin carbamate prodrug represented by formula 3-N or 7-N and a pharmaceutically acceptable salt thereof, and a preparation method therefor and the use thereof. Specifically, the icaritin carbamate prodrug is formed by subjecting a main metabolic site (3-site or 7-site hydroxyl) of a natural flavonoid compound icaritin to structural modification by means of a chemical synthesis method, and introducing a suitable group at the position. Amines used in such carbamates are aliphatic amines. The presence of the carbamate structure reduces the phase II metabolism of icaritin in SD rats. Compared with an icaritin bulk drug, the 3-N-01 prodrug has a significantly improved oral bioavailability, making same the optimal prodrug. In clinical medication, the prodrug is expected to be able to reduce the administration dosage and improve patient compliance, and is expected to offer an effective strategy for improving the oral bioavailability of phenolic drugs.
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主要参考文献


1: Liao J, Liu Y, Wu H, Zhao M, Tan Y, Li D, Long H, Dai Y, Yung S, Chan TM, Lu Q. The role of icaritin in regulating Foxp3/IL17a balance in systemic lupus erythematosus and its effects on the treatment of MRL/lpr mice. Clin Immunol. 2016 Jan;162:74-83. doi: 10.1016/j.clim.2015.11.006. Epub 2015 Nov 18. doi: 10.3892/or.2015.4335. Epub 2015 Oct 16. Chinese. doi: 10.18632/oncotarget.5578. doi: 10.1142/S0192415X15500627. Epub 2015 Sep 14. doi: 10.1111/1440-1681.12488. doi: 10.1016/j.ejmech.2015.06.006. Epub 2015 Jun 6. doi: 10.11817/j.issn.1672-7347.2015.05.010. Chinese. doi: 10.1016/j.biomaterials.2015.04.038. Epub 2015 May 15. Chinese. doi: 10.1093/carcin/bgv040. Epub 2015 Apr 23.
13: Wu T, Wang S, Wu J, Lin Z, Sui X, Xu X, Shimizu N, Chen B, Wang X. Icaritin induces lytic cytotoxicity in extranodal NK/T-cell lymphoma. J Exp Clin Cancer Res. 2015 Feb 15;34:17. doi: 10.1186/s13046-015-0133-x.
14: Zhu S, Wang Z, Li Z, Peng H, Luo Y, Deng M, Li R, Dai C, Xu Y, Liu S, Zhang G. Icaritin suppresses multiple myeloma, by inhibiting IL-6/JAK2/STAT3. Oncotarget. 2015 Apr 30;6(12):10460-72.

合成参考文献


参考文献:10.1002/term.1679
摘要:Xie XH, Wang XL, Zhang G, He YX, Leng Y, Tang TT, Pan X, Qin L. Biofabrication of a PLGA-TCP-based porous bioactive bone substitute with sustained release of icaritin. J Tissue Eng Regen Med. 2015 Aug;9(8):961–72. doi: 10.1002/term.1679.
摘要:Zhang S, Sun L, Huang Z. [Tissue distribution of glucuronidated icaritin metabolite in rats]. Wei Sheng Yan Jiu. 2015 Jul;44(4):692–4.
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