CAS: 84472-89-9; Cytidine, 3′-Azido-2′,3′-Dideoxy-

该化合物是一种经过修改的核核素模拟,其特点是替换3'azido组,在肋骨环的2'和3'位置上没有氢氧基,这种结构改变可阻抗酶降解,使其在核酸研究和抗病毒药物开发中具有价值. 处于3's 位置的azido组可以通过点击化学进一步功能化,加强其在生物合成和探测设计中的效用. 它的稳定性和再活性使它成为合成生物学和药用化学的多功能中间体,特别是在基于核素的治疗研究中.

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MSDS等安全信息

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    CAS号87190-76-9 [(2S,3S,5R)-3-a... | CAS号84472-88-8 5'-O-acetyl-3'-... | CAS号84472-85-5 那尿苷 | CAS号84472-87-7 Uridine,3'-azid... | CAS号14270-73-6 5'-O-三苯甲基-2'-脱氧尿苷 | CAS号84472-84-4 Uridine,3'-azid... | CAS号6038-53-5 1-[4-methylsulf... | CAS号5983-03-9 1-[4-methylsulf... | CAS号84472-83-3 1-[4-hydroxy-5-... | CAS号84472-90-2 3’-氨基-2’,3’-二脱氧胞苷

    合成工艺路线路线简述

    • 合成目标产物 3'-Azido-2'-Deoxy-D-Cytidine 主要起始原料 3'-Azido-2',3'-Dideoxyuridine
    • (文献来源)合成步骤主要原料 3'-Azido-2',3'-Dideoxyuridine
    📜Navuridine置于甲醇,Ammonium Sulfate,Formamide,六甲基二硅氮烷体系中,化学反应生成 3'-叠氮-2',3'-双脱氧胞苷
    参考文献:一些嘧啶的3'-氨基-2',3'-二脱氧核糖核苷:合成和生物活性.
    标题:一些嘧啶的3'-氨基-2',3'-二脱氧核糖核苷:合成和生物活性.
    摘要:胸腺嘧啶,尿嘧啶和5-碘尿嘧啶的3'-氨基-2',3'-二脱氧核糖核苷(1-3)是通过相应的2'-脱氧核糖核苷通过threo-3'-Chloro和erythro-3'-合成的叠氮基衍生物.以3'-氨基-2',3'-二脱氧胸苷为氨基戊糖基供体,以胸苷磷酸化酶(ec 2.4.2.4)为酶促合成了5-溴尿嘧啶,5-氯尿嘧啶和5-氟尿嘧啶(4-6)的相应氨基核苷催化剂.通过氨基化3'-氨基-2',3'-二脱氧尿苷的3'-叠氮基前体合成3'-氨基-2',3'-二脱氧胞苷(7).在这组氨基核苷中,3'-氨基-2',3'-二脱氧-5-氟尿苷的生物活性显着(6).它对腺病毒的ed50为10 Microm,对培养的哺乳动物细胞没有明显的细胞毒性.它也对某些革兰氏阳性细菌有活性,但对多种革兰氏阴性细菌没有活性.其他氨基核苷(1-5和7)缺乏或表现出弱的抗病毒和抗菌活性.该组中唯一对培养的哺乳动物细胞有明显毒性
    DOI:10.1021/jm00360A019

    海关参考信息

    专利信息


    专利号:US-11858953-B2
    优先权日:2018-04-04
    标 题:Compositions and methods for synthesis of phosphorylated molecules
    发明人:CHAPUT JOHN; LIAO JEN-YU; BALA SAIKAT
    权利人:UNIV CALIFORNIA
    摘要:The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

    专利号:US-2020239500-A1
    优先权日:2018-04-04
    标 题 :Compositions and Methods for Synthesis of Phosphorylated Molecules

    专利号:US-2021332070-A1
    优先权日:2018-04-04
    标题:Compositions and Methods for Synthesis of Phosphorylated Molecules

    专利号:US-11021497-B2
    优先权日:2018-04-04
    标题 :Compositions and methods for synthesis of phosphorylated molecules

    专利号:WO-9210496-A1
    优先权日:1990-12-05
    标 题:ENANTIOMERICALLY PURE β-L-(-)-1,3-OXATHIOLANE NUCLEOSIDES
    发明人:CHU CHUNG K; BEACH J WARREN; JEONG LAK-SHIN
    权利人:UNIV GEORGIA RES FOUND
    摘要:An asymmetric process for the preparation of enantiomerically pure β-L-(-)-1,3-oxathiolane-nucleosides that includes the initial preparation of the key chiral intermediates (2R,5R) and (2R,5S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane from 1,6-thioanhydro-L-gulose. The 2R,5(R,S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane is condensed with a desired heterocyclic base, typically a purine or pyrimidine base, to provide the product nucleoside. The synthesis can be used to prepare the pharmaceutically important compound, β-L-(-)-1-[(2β,4β)-2-(hydroxymethyl)-4-(1,3-thioxolane)]cytosine (β-L-(-)BCH-189).

    专利号:US-5248776-A
    优先权日:1990-12-05
    标题 :Process for enantiomerically pure β-L-1,3-oxathiolane nucleosides
    发明人:CHU CHUNG K; JEONG LAK-SHIN; BEACH J WARREN
    权利人:UNIV GEORGIA RES FOUND
    摘要:An asymmetric process for the preparation of enantiomerically pure β-L-(-)-1,3-oxathiolane-nucleosides that includes the initial preparation of the key chiral intermediates (2R,5R) and (2R,5S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane from 1,6-thioanhydro-L-gulose. The 2R,5(R,S)-5-(O-protected)-2-(protected-oxymethyl)-1,3-oxathiolane is condensed with a desired heterocyclic base, typically a purine or pyrimidine base, to provide the product nucleoside. The synthesis can be used to prepare the pharmaceutically important compound, β-L-(-)-1-[(2β,4β)-2-(hydroxymethyl)-4-(1,3-thioxolane)]cytosine (β-L-(-)BCH-189).

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    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

    合成参考文献


    参考文献:10.1016/0006-2952(88)90049-4
    摘要:Balzarini J, Baba M, Pauwels R, Herdewijn P, De Clerq E. Anti-retrovirus activity of 3'-fluoro- and 3'-azido-substituted pyrimidine 2',3'-dideoxynucleoside analogues. Biochem Pharmacol. 1988 Jul 15;37(14):2847–56. doi: 10.1016/0006-2952(88)90049-4.
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