CAS: 4294-16-0; (2R,3R,4S,5R)-2-(6-(Benzylamino)-9H-Purin-9-yl)-5-(Hydroxymethyl)Tetrahydrofuran-3,4-Diol

该化合物是腺素的合成衍生物,是细胞能量转移和信号信号中具有关键作用的核核素,该化合物的特性是附于腺素氮原子的一个苯基组,它比亚丁素更具亲脂性.Benzyladenosine展示了能够使其与各种生物受体,特别是登氧素受体相互作用的特性,这些受体参与了许多生理过程,包括...

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58-61-7 1867-73-8 5536-17-4

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CAS号2004-06-0 6-氯嘌呤核苷 | CAS号100-46-9 苄胺 | CAS号58-63-9 肌苷 | CAS号3287-99-8 苄胺盐酸盐 | CAS号100-52-7 苯甲醛 | CAS号58-61-7 腺苷 | CAS号3181-38-2 2',3',5'-三乙酰肌苷 | CAS号932-90-1 苯甲醛肟 | CAS号58-61-7 腺苷 | CAS号34408-14-5 8-氯腺嘌呤核苷 | CAS号78188-38-2 2',3'-O-(1-甲基亚乙... | CAS号2946-39-6 8-溴腺苷 | CAS号1214-39-7 6-苄氨基嘌呤 | CAS号18646-11-2 α-D-ribofuranos... | CAS号13484-66-7 Benzyl-amp

合成工艺路线路线简述

    6-N-2',3',5'-Tri-O-Tetraacetyladenosine置于甲醇,氨,Potassium Carbonate体系中,用 N,N-二甲基甲酰胺 作为反应溶剂,化学反应 68.0H,反应生成 6-苄基腺苷
    参考文献:N6-乙酰基-2',3',5'-三-O-乙酰腺苷;区域选择性n6-烷基化的便捷"缺失"底物
    标题:N6-乙酰基-2',3',5'-三-O-乙酰腺苷;区域选择性n6-烷基化的便捷"缺失"底物
    摘要:在咪唑存在下,在室温下用甲醇对五乙酰基腺苷2进行选择性的n-脱乙酰基化反应,建立了一种简单有效的n 6-乙酰基2',3',5'-Tri-O-乙酰腺苷(1)路线. .利用2和1的粗混合物,通过腺苷与乙酸酐在吡啶中在升高的温度下反应制备的混合物,详细说明了1的制备合成.从腺苷开始,总产率为1,为80-85%.结果表明1是选择性n 6的便捷底物-烷基化.该研究揭示了在1与活化的烷基卤化物的碱促进反应和1与醇的光延反应中相同的区域选择性.制备了一系列的n 6-烷基腺苷5A-F.通过使用核苷磷酸化酶和碱性磷酸酶的组合对母体核苷衍生物5B,D,E进行酶促转化来制备细胞分裂素6B,D,E. 细胞分裂素-腺苷衍生物-N 6-烷基化-区域选择性-Mitsunobu反应-核苷磷酸化酶
    DOI:10.1055/s-0030-1260090

    海关参考信息

    专利信息


    专利号:US-6329519-B1
    优先权日:1996-06-13
    标 题:Intermediates for oligonucleotide synthesis
    发明人:COLLINGWOOD STEPHEN PAUL; MOSER HEINZ ERNST; ALTMANN KARL-HEINZ; DOUGLAS MARK EDWARD
    权利人:ISIS PHARMACEUTICALS INC
    摘要:A compound of formula (I) wherein B 1 is a radical of a nucleoside base, R 1 is hydrogen or a hydroxy-protecting group, R 2 is hydrogen, hydroxy or a 2′-nucleoside-modifying atom or group, R 3 is an unsubstituted or substituted C 1 to C 10 alkyl, C 2 to C 10 alkenyl, C 4 to C 10 cycloalkylalkyl, C 6 to C 10 aryl or C 7 to C 13 aralkyl group, and Z is halogen or a group of formula (II) where R 4 and R 5 are each independently an unsubstituted or substituted C 1 to C 10 alkyl, C 2 to C 10 alkenyl, C 4 to C 10 cycloalkylalkyl, C 6 to C 10 aryl or C 7 to C 13 aralkyl group, or R 4 is said group and R 5 is hydrogen or R 4 and R 5 together with the nitrogen atom to which they are attached denote a five- to thirteen-membered heterocyclic ring, or Z is a group of formula (III): Nuc-O—, where Nuc is the residue of a natural or synthetic nucleoside or oligonucleotide after removal of a 5′-hydroxyl group therefrom attached through a 5′-methylene thereof to the indicated oxygen atom.

    专利号:US-2023241088-A1
    优先权日:2022-01-17
    标 题 :Composition for preventing or treating lung cancer comprising ortho-topolin riboside as active ingredient
    发明人:CHOI HYUNG-KYOON; LEE HWANHUI
    权利人:CHUNG ANG UNIV INDUSTRY ACADEMY COOPERATION FOUNDATION
    摘要:The present disclosure relates to a composition for preventing or treating lung cancer, including ortho topolin riboside (oTR) as an active ingredient, wherein oTR showed the highest cytotoxicity among all tested compounds against NSCLC cells, oTR reduced synthesis of amino acid and pyrimidine as well as glycolytic function in NSCLC cells and xenograft tumors.
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    主要参考文献

    [参考文献]: Castiglioni S, Et Al. N6-Isopentenyladenosine And Its Analogue N6-Benzyladenosine Induce Cell Cycle Arrest And Apoptosis In Bladder Carcinoma T24 Cells. Anticancer Agents Med Chem. 2013 May;13(4):672-8.
    [参考文献]: Grimaldi M, Et Al. Nmr For Screening And A Biochemical Assay: Identification Of New Fpps Inhibitors Exerting Anticancer Activity. Bioorg Chem. 2020 May;98:103449.
    [参考文献]: Kaminek M, Et Al. Cytokinin Activities Of N6-Benzyladenosine Derivatives Hydroxylated On The Side-Chain Phenyl Ring. Journal Of Plant Growth Regulation. 1987. 6(2):113.
    [参考文献]: Kim Ya, Et Al. Synthesis, Biological Evaluation And Molecular Modeling Studies Of N6-Benzyladenosine Analogues As Potential Anti-Toxoplasma Agents. Biochem Pharmacol. 2007 May 15;73(10):1558-72.
    [参考文献]: Mlejnek P. Caspase Inhibition And N6-Benzyladenosine-Induced Apoptosis In Hl-60 Cells. J Cell Biochem. 2001;83(4):678-89.

    合成参考文献


    参考文献:10.1111/j.1749-6632.1986.tb48041.x
    摘要:LEONARD NJ, CRUICKSHANK KA, GROZIAK MP, CLAUSON GL, DEVADAS B. Relatives of Watson‐Crick DNA, RNA Cross Sectionsa. Annals of the New York Academy of Sciences. 1986 Jun;471(1):255–65. doi: 10.1111/j.1749-6632.1986.tb48041.x.
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