CAS: 19057-67-1; (2S,3R,4R,5R,6S)-2-(((2R,3R,4S,5S,6R)-4,5-Dihydroxy-6-(Hydroxymethyl)-2-(((4S,5'R,6Ar,6Bs,8As,8Br,9S,10R,11As,12As,12Bs)-5',6A,8A,9-Tetramethyl-1,3,3',4,4',5,5',6,6A,6B,6',7,8,8A,8B,9,11A,12,12A,12B-Icosahydrospiro[naphtho[2',1':4,5]Indeno[2,1-B]Furan-10,2'-Pyran]-4-yl)Oxy)Tetrahydro-2H-Pyran-3-yl)Oxy)-6-Methyltetrahydro-2H-Pyran-3,4,5-Triol

该化合物是一种以潜在生物活性特性而闻名的三乙基沙皮因衍生物,其作为合成各种药用活性化合物的前体的作用通常受到研究.Prosapogenin A展示了有助于其稳定性和生物利用率的结构特征,使其成为制药研究的宝贵中间体.其定义明确的化学结构允许精确的修改,有利于开发具有定向生物活动的衍生物.该化合物经常用于研究反炎,抗癌和免疫分子作用.其纯性和一致性对于可复制的实验结果至关重要,强调了其在学术和工业研究环境中的重要性.

结构式图片

上下游产品

2)>-4)>-β-D-glucopyranosidediosgenin 3-O-α-L-rhamnopyranosyl(1*2)-β-D-glucopyranosyl(1*4)-β-D-glucopyranoside 4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside(3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1-4)-[α-L-rhamnopyranosyl-(1-2)]-β-D-glucopyranoside 2)-O-β-D-glucopyranoside>(25R)-26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,22ξ,26-triol 3-O-2)-O-β-D-glucopyranoside dioscin diosgenin trillin

合成工艺路线路线简述

    📜Diosgenyl 2-O-(2,3,4-Tri-O-Acetyl-α-L-Rhamnopyranosyl)-4,6-O-Benzylidene-3-O-Pivaloyl-β-D-Glucopyranoside置于溶剂黄146,甲醇,Sodium Methylate体系中,用 二氯甲烷 用作溶剂,化学反应 2.0H,以41%的收率获得重楼皂苷e
    参考文献:Synthesis Of Novel Spirostanic Saponins And Their Cytotoxic Activity
    标题:Synthesis Of Novel Spirostanic Saponins And Their Cytotoxic Activity
    摘要:This Study Was Carried Out To Assess The Cytotoxicity Of Several New Synthetic Steroidal Saponins Against The Human Myeloid Leukemia Cell Lines (Hl-60 And U937) And Against Human Melanoma Cells (Sk-Mel-1). Several Diosgenyl Glycosides Analyzed Showed Strong Cell Growth Inhibition Which Was Associated With Alterations In Cell Cycle Progression And Induction Of Apoptosis. Studies Of Cytochrome C Release And Caspase-9 Activation Suggest A Main Role Of The Intrinsic Pathway Of Apoptosis In The Mechanism Of Cytotoxicity Caused By This Kind Of Compounds. (C) 2007 Elsevier Ltd. All Rights Reserved.
    Doi:10.1016/j.Bmc.2007.10.089

    海关参考信息

    专利信息


    专利号:US-9718850-B2
    优先权日:2008-04-08
    标题:Triterpene saponins, methods of synthesis and uses thereof
    发明人:GIN DAVID; ADAMS MICHELLE; DENG KAI; LIVINGSTON PHILIP; RAGUPATHI GOVINDASWAMI; CHEA ERIC; FERNANDEZ-TEJADA ALBERTO; NORDSTROEM LARS ULRIK; Walkowicz William; GARDNER JEFFREY; TAN DEREK
    权利人:MEMORIAL SLOAN-KETTERING INST FOR CANCER RES
    摘要:The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

    专利号:US-2017283450-A1
    优先权日:2008-04-08
    标题 :Triterpene saponins, methods of synthesis and uses thereof

    专利号:KR-102453184-B1
    优先权日:2008-04-08
    标 题:Triterpene saponins, methods of synthesis, and uses thereof

    专利号:US-2013011421-A1
    优先权日:2008-04-08
    标题 :Triterpene saponins, methods of synthesis, and uses thereof

    专利号:US-8283456-B2
    优先权日:2008-04-08
    标 题 :Triterpene saponins, methods of synthesis, and uses thereof

    专利号:AU-2017258850-B2
    优先权日:2008-04-08
    标题 :Triterpene saponins, methods of synthesis, and uses thereof

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Wang TX, Zhang ZQ, Cong Y, Shi XY, Liu YH, Zhao FL. Prosapogenin A induces apoptosis in human cancer cells in vitro via inhibition of the STAT3 signaling pathway and glycolysis. Oncol Lett. 2013 Nov;6(5):1323-1328. Epub 2013 Sep 4.
    2: Wang TX, Shi XY, Cong Y, Zhang ZQ, Liu YH. [Prosapogenin A inhibits cell growth of MCF7 via downregulating STAT3 and glycometabolism-related gene]. Yao Xue Xue Bao. 2013 Sep;48(9):1510-4. Chinese. doi: 10.1080/10286020.2013.825253. Epub 2013 Aug 14. German. doi: 10.5142/jgr.2012.36.1.102.
    9: VOIGTLANDER HW, ROSENBERG W. [Prosapogenin GB (beta-aescin). A contribution to the chemistry of horse chestnut saponins]. Arzneimittelforschung. 1963 May;13:385-6. German. Chinese. Japanese. Chinese. doi: 10.1016/j.carres.2014.11.011. Epub 2014 Nov 29. doi: 10.1002/pca.2342. Epub 2012 Mar 9.

    合成参考文献


    参考文献:10.1248/cpb.55.308
    摘要:Yoshikawa M, Xu F, Morikawa T, Pongpiriyadacha Y, Nakamura S, Asao Y, Kumahara A, Matsuda H. Medicinal flowers. XII.(1)) New spirostane-type steroid saponins with antidiabetogenic activity from Borassus flabellifer. Chem Pharm Bull (Tokyo). 2007 Feb;55(2):308–16. doi: 10.1248/cpb.55.308.
    参考文献:10.1126/science.1174621
    摘要:Lingwood D, Simons K. Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 01;327(5961):46–50. doi: 10.1126/science.1174621.
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