CAS: 33570-04-6; Bilobalide

结构式图片

上下游产品

10-O-Acetylbilobalid 10,12-Di-O-acetyl-iso-bilobalid 10-O-Acetyl-12-O-(p-brombenzoyl)-iso-bilobalid 3-bromo-4,4-dimethyl-2-pentenal12-O-Pivaloyl-iso-bilobalid 8,10-Di-O-pivaloylbilobalid 10,12-Di-O-Pivaloyl-iso-bilobalid 10-O-Acetylbilobalid

合成工艺路线路线简述

    (-)-Des-Hydroxybilobalide置于4-二甲氨基吡啶,双(三甲基硅烷基)氨基钾体系中,用 四氢呋喃 用作溶剂,化学反应 27.0H,反应生成白果内酯
    参考文献:银杏叶化学空间在反应生成(-)-Bilobalide 的过程中的合成,机理和生物学研究
    标题:银杏叶化学空间在反应生成(-)-Bilobalide 的过程中的合成,机理和生物学研究
    摘要:在这里,我们探讨了结构致密 (1.63 Mcbits/å3) Gabaa 受体拮抗剂白果内酯,其合成过程中的中间体以及相关的机制问题. 13C 同位素标记可识别出在 α 选择性催化不对称 Reformatsky 反应途中发生的意外溴迁移,从而排除了不对称烯丙基化途径.实验和计算集中于两个令人惊讶的观察结果背后的驱动力.首先,氧杂环丁烷缩醛在浓无机酸中持久存在(1.5 M Dcl,溶于 Thf-D8/d2O);其寿命与开环时取代基之间不稳定的空间冲突有关.其次,发现脱羟基白果内酯的区域选择性氧化依赖于通过孤对离域的内酯酸化,这导致极快的分子间烯醇化物平衡.我们还使用 (+)-白果内酯作为阴性对照,建立了 (-)-白果内酯和非惊厥倍半萜 (-)-Jiadifenolide 对 Gaba 能突触的动作电位独立抑制电流的等效作用. Bilob-Alide 的高信息密度使其有别于其他支架,并且可以更
    Doi:10.1021/jacs.0C08231

    海关参考信息

    专利信息


    专利号:US-7598291-B2
    优先权日:2004-09-02
    标题 :Methods and compositions for enhancing collagen and proteoglycan synthesis in the skin
    发明人:NIMNI MARCEL; HAN BO
    权利人:NIMNI MARCEL; HAN BO
    摘要:A composition for application to the skin can stimulate the in vivo synthesis of collagen and proteoglycans and improve the appearance of the skin, increasing its elasticity and fullness. In general, a composition according to the present invention comprises: (1) an antioxidant compound in a quantity sufficient to enhance collagen synthesis in the skin; (2) an organic penetrant in which the antioxidant compound is soluble in a sufficient quantity that a concentration of the antioxidant compound sufficient to enhance collagen synthesis can be applied topically and penetrate the skin; (3) a mixture of essential amino acids; (4) a supplemental source of sulfur; and (5) a topical pharmaceutically acceptable carrier. The antioxidant compound can be lipoic acid, a lipoic acid analogue or derivative, a bioflavonoid, a constituent of ginkgo, or an isoflavone. The organic penetrant is preferably benzyl alcohol. Other ingredients, such as esters of tocopherol and ascorbic acid, can be included.

    专利号:US-2010160244-A1
    优先权日:2004-09-02
    标 题 :Methods and compositions for enhancing collagen, proteoglycan, and glutathione synthesis in the skin
    发明人:NIMNI MARCEL; HAN BO
    权利人:NIMNI MARCEL; HAN BO
    摘要:A composition for application to the skin can stimulate the in vivo synthesis of collagen and proteoglycans and improve the appearance of the skin, increasing its elasticity and fullness. In general, a composition according to the present invention comprises: (1) an antioxidant compound in a quantity sufficient to enhance collagen synthesis in the skin; (2) an organic penetrant in which the antioxidant compound is soluble in a sufficient quantity that a concentration of the antioxidant compound sufficient to enhance collagen synthesis can be applied topically and penetrate the skin; (3) a mixture of essential amino acids or hydrolyzed whey protein; (4) a supplemental source of sulfur; and (5) a topical pharmaceutically acceptable carrier. The antioxidant compound can be lipoic acid or a lipoic acid analogue or derivative. The organic penetrant is preferably benzyl alcohol. Other ingredients, such as esters of tocopherol and ascorbic acid, can be included.

    专利号:US-7429670-B2
    优先权日:2003-08-27
    标题 :Synthesis of derivatives of ginkgolide C
    发明人:NAKANISHI KOJI; JARACZ STANISLAV; STROMGAARD KRISTIAN
    权利人:UNIV COLUMBIA
    摘要:The subject invention provides ginkgolide C derivatives compounds having the structure: n n n n n n n n n n wherein R is H or -A-Ar,n where A is an alkyl group; and Ar is an aryl group, which may contain heteroatoms and may be unsubstituted or substituted by one to five substituents each selected from the group consisting of hydrogen, alkoxy, —CH 2 CO 2 R 4 , and —CH 2 CONR 5 R 6 ;n where R 4 is an alkyl group; and R 5 and R 6 are each, independently, hydrogen or a branched or unbranched alkyl group; n n n wherein R 1 is H or —COR 7 ,n where R 7 is alkyl, aryl or amino; n n wherein R 2 is present or absent, and when present is H, —COR 8 or —CO—Z—R 8 ;n where R 8 is alkyl, aryl or amino; and Z is oxygen; n n wherein R 3 is present or absent, and when present is —COR 9 ;n where R 9 is alkyl or aryl; n n wherein only one of R 2 or R 3 is present in the compound; n wherein only two of R, R 1 , R 2 and R 3 are H; and n wherein each of a and b designates a single covalent bond which is present or absent,n where bond a is present when R 3 is absent and bond b is present when R 2 is absent;n nor an optically pure enantiomer of the compound. Additionally, the subject invention provides methods of inhibiting the activity of a glycine receptor using these compounds.

    专利号:US-2024239805-A1
    优先权日:2022-12-16
    标 题:Aza-yang cyclization-buchner aromatic ring expansion: collective synthesis of cycloheptatriene-containing azetidine lactones
    发明人:SINGH MANVENDRA PAL; BOSKOVIC ZARKO; GASKINS BRYCE
    权利人:UNIV KANSAS
    摘要:The present disclosure is directed to a compound of Formula I, Formula II, Formula III, Formula IV, or Formula Vor a pharmaceutically acceptable salt and/or solvate thereof.

    专利号:US-6693091-B2
    优先权日:2002-03-29
    标 题 :Analogs of terpene trilactones from Ginkgo biloba for bioorganic and imaging studies
    发明人:STROMGAARD KRISTIAN; SUEHIRO MAKIKO; NAKANISHI KOJI
    权利人:UNIV COLUMBIA
    摘要:A compound having the structure: n wherein R 1 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; n wherein R 2 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; n wherein R 3 is H or OH; n wherein R 4 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; and n wherein at least one of R 1 , R 2 , R 3 , or R 4 is a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety. Optically pure enantiomers and salts of the compound are also described. Also, the synthesis of the compound, and uses of the compound, such as in a method for detecting the localization of, or identifying, receptors, enzymes or other targets, whether in a cell or in a subject.

    专利号:US-2009221019-A1
    优先权日:2005-06-22
    标 题:Core-Modified Terpene Trilactones From Ginkgo Biloba Extract and Biological Evaluation Thereof
    发明人:NAKANISHI KOJI; DZYUBA SERGEI; ISHII HIDEKI
    权利人:NAKANISHI KOJI; DZYUBA SERGEI; ISHII HIDEKI
    摘要:Lactone-rings of ginkgolides are converted into the corresponding tetrahydrofuran moieties via DIBAL-H reduction followed by deoxygenation of the formed lactols with Et 3 SiH/BF 3 Et 2 O producing a series of lactol-free ginkgolides. The present invention also relates to synthesis of hydroxyl-free, or hydroxyl-free and lactone-free, ginkgolides and bilobalides.
    北京海步国际医药科技发展有限公司
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    主要参考文献


    1: Qian YX, Kang JC, Luo YK, Zhao JJ, He J, Geng K. A Bilobalide-Producing Endophytic Fungus, Pestalotiopsis uvicola from Medicinal Plant Ginkgo biloba. Curr Microbiol. 2016 May 7. [Epub ahead of print] doi: 10.1016/j.ejphar.2016.03.007. Epub 2016 Mar 4. doi: 10.1111/ced.12664. Epub 2015 Jul 14. doi: 10.1002/bmc.3515. Epub 2015 Jul 23. doi: 10.1186/s12974-014-0167-6.
    6: Huang P, Zhang L, Chai C, Qian XC, Li W, Li JS, Di LQ, Cai BC. Effects of food and gender on the pharmacokinetics of ginkgolides A, B, C and bilobalide in rats after oral dosing with ginkgo terpene lactones extract. J Pharm Biomed Anal. 2014 Nov;100:138-44. doi: 10.1016/j.jpba.2014.07.030. Epub 2014 Aug 2. doi: 10.3109/10715762.2014.945442. doi: 10.1007/s10571-014-0072-7. Epub 2014 May 18. doi: 10.1016/j.jpba.2014.03.003. Epub 2014 Mar 12. Chinese. doi: 10.1016/j.brainres.2013.07.003. Epub 2013 Jul 11. doi: 10.1097/FBP.0b013e32836360ab. doi: 10.3892/mmr.2013.1573. Epub 2013 Jul 8. doi: 10.1016/j.pbb.2013.03.005. Epub 2013 Mar 26. doi: 10.1016/j.phymed.2012.09.015. Epub 2012 Oct 17. doi: 10.1016/j.ejphar.2011.12.011. Epub 2011 Dec 16. doi: 10.1016/j.brainres.2011.10.005. Epub 2011 Oct 6.
    19: Lau AJ, Yang G, Rajaraman G, Baucom CC, Chang TK. Species-dependent and receptor-selective action of bilobalide on the function of constitutive androstane receptor and pregnane X receptor. Drug Metab Dispos. 2012 Jan;40(1):178-86. doi: 10.1124/dmd.111.042879. Epub 2011 Oct 21. doi: 10.1007/s11064-011-0612-1. Epub 2011 Sep 28.

    合成参考文献


    参考文献:10.1124/mol.119.115964
    摘要:Lee TD, Lee OW, Brimacombe KR, Chen L, Guha R, Lusvarghi S, Tebase BG, Klumpp-Thomas C, Robey RW, Ambudkar SV, Shen M, Gottesman MM, Hall MD. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular Pharmacology. 2019 Nov;96(5):629–40. doi: 10.1124/mol.119.115964.
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