5-propynyl-2'-O-allyluridine | 151091-80-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-propynyl-2'-O-allyluridine
• 英文别名: 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-enoxyoxolan-2-yl]-5-prop-1-ynylpyrimidine-2,4-dione
• CAS: 151091-80-4
• 化学式: C₁₅H₁₈N₂O₆
• 分子量: 322.318
• InChiKey: IMXUCODZTNLRKA-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 5-propynyl-2'-O-allyluridine 在 吡啶 作用下， 反应 18.0h， 生成 1-{(2R,3R,4R,5R)-3-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-prop-1-ynyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Oligonucleotides derived from 5-(1-propynyl)-2′-O-allyl-uridine and 5-(1-propynyl)-2′-O-allyl-cytidine: Synthesis and RNA duplex formation

  摘要：

  The protected nucleoside analogs of 5-(1-propynyl)-2'-O-allyl-uridine and 5-(1-propynyl)-2'-O-allyl-cytidine are described. Oligonucleotides containing this modification significantly enhance double-helix formation with single-strand RNA.

  DOI：

  10.1016/s0040-4039(00)77476-4
• 作为产物：
  描述：

  1-((2R,3R,3aR,9aR)-3-Allyloxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-5-prop-1-ynyl-1H-pyrimidine-2,4-dione 在 四氢呋喃 、 四丁基氟化铵 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 5-propynyl-2'-O-allyluridine
  参考文献：
  名称：

  Oligonucleotides derived from 5-(1-propynyl)-2′-O-allyl-uridine and 5-(1-propynyl)-2′-O-allyl-cytidine: Synthesis and RNA duplex formation

  摘要：

  The protected nucleoside analogs of 5-(1-propynyl)-2'-O-allyl-uridine and 5-(1-propynyl)-2'-O-allyl-cytidine are described. Oligonucleotides containing this modification significantly enhance double-helix formation with single-strand RNA.

  DOI：

  10.1016/s0040-4039(00)77476-4

文献信息

• Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines
  申请人：——

  公开号：US20030170680A1

  公开（公告）日：2003-09-11

  Novel oligomers are disclosed which have enhanced ability with respect to forming duplexes or triplexes compared with oligomers containing only conventional bases. The oligomers contain the bases 5-(1-propynyl)uracil, 5-(1-propynyl)cytosine or related analogs. The oligomers of the invention are capable of (i) forming triplexes with various target sequences such as virus or oncogene sequences by coupling into the major groove of a target DNA duplex at physiological pH or (ii) forming duplexes by binding to single-stranded DNA or to RNA encoded by target genes. The oligomers of the invention can be incorporated into pharmaceutically acceptable carriers and can be constructed to have any desired sequence, provided the sequence normally includes one or more bases that is replaced with the analogs of the invention. Compositions of the invention can be used as pharmaceutical agents to treat various diseases such as those caused by viruses and can be used for diagnostic purposes in order to detect viruses or disease conditions.

  本发明揭示了一种新型寡聚物，与仅含传统碱基的寡聚物相比，具有增强的形成双链或三链的能力。该寡聚物包含5-（1-丙炔基）尿嘧啶，5-（1-丙炔基）胞嘧啶或相关类似物的碱基。本发明的寡聚物能够（i）通过在生理pH值下与靶DNA双链的主沟结合，形成与各种靶序列（如病毒或癌基因序列）的三链，或（ii）通过结合单链DNA或靶基因编码的RNA而形成双链。本发明的寡聚物可以被纳入药学可接受的载体中，并且可以构建任何所需的序列，只要序列通常包括一个或多个被本发明类似物替换的碱基。本发明的组合物可以用作制药剂治疗各种由病毒引起的疾病，并可用于诊断目的，以检测病毒或疾病情况。
• ENHANCED TRIPLE-HELIX AND DOUBLE-HELIX FORMATION WITH OLIGOMERS CONTAINING MODIFIED PYRIMIDINES
  申请人：——

  公开号：US20040265802A9

  公开（公告）日：2004-12-30

  Novel oligomers are disclosed which have enhanced ability with respect to forming duplexes or triplexes compared with oligomers containing only conventional bases. The oligomers contain the bases 5-(1-propynyl)uracil, 5-(1-propynyl)cytosine or related analogs. The oligomers of the invention are capable of (i) forming triplexes with various target sequences such as virus or oncogene sequences by coupling into the major groove of a target DNA duplex at physiological pH or (ii) forming duplexes by binding to single-stranded DNA or to RNA encoded by target genes. The oligomers of the invention can be incorporated into pharmaceutically acceptable carriers and can be constructed to have any desired sequence, provided the sequence normally includes one or more bases that is replaced with the analogs of the invention. Compositions of the invention can be used as pharmaceutical agents to treat various diseases such as those caused by viruses and can be used for diagnostic purposes in order to detect viruses or disease conditions.

  本发明披露了一种新型寡聚物，与仅含传统碱基的寡聚物相比，其具有增强的双链或三链形成能力。该寡聚物包含碱基5-(1-丙炔基)尿嘧啶，5-(1-丙炔基)胞嘧啶或相关类似物。本发明的寡聚物能够(i)在生理pH下通过耦合到目标DNA双链的主沟槽形成三链，如病毒或癌基因序列，或(ii)通过结合到单链DNA或由目标基因编码的RNA形成双链。本发明的寡聚物可以被纳入到药学可接受的载体中，并且可以构建任何所需的序列，只要该序列通常包括一个或多个被本发明的类似物替换的碱基。本发明的组合物可以用作制药剂治疗各种疾病，如由病毒引起的疾病，并且可以用于诊断目的，以检测病毒或疾病情况。
• Novel nucleoside and oligonucleotide analogues
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20020147332A1

  公开（公告）日：2002-10-10

  A compound of the formula (1): 1 wherein R 1 and R 2 are the same or different and represent a hydrogen atom, a hydroxyl protecting group, a phosphate group, or —P(R 3 )R 4 , wherein R 3 and R 4 are the same or different and represent a hydroxyl group, an amino group, an alkoxy group having from 1 to 4 carbon atoms, a cyanoalkoxy group having from 1 to 5 carbon atoms or an amino group substituted by an alkyl group having from 1 to 4 carbon atoms; A represents an alkylene group having from 1 to 4 carbon atoms and B represents a purin-9-yl group, a 2-oxo-pyrimidin-1-yl group, a substituted purin-9-yl group or a substituted 2-oxo-pyrimidin-1-yl group having a substituent &agr; selected from the group consisting of a hydroxyl group which may be protected, an alkoxy group having from 1 to 4 carbon atoms, a mercapto group which may be protected, an alkylthio group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an amino group which may be protected, a mono- or di-alkylamino group which may be substituted by an alkyl group having from 1 to 4 carbon atoms, an alkyl group having from 1 to 4 carbon atoms and a halogen atom; or a salt thereof.

  化合物的式子（1）：1其中R1和R2相同或不同，表示氢原子，羟基保护基，磷酸基或-P（R3）R4，其中R3和R4相同或不同，表示羟基，氨基，具有1至4个碳原子的烷氧基，具有1至5个碳原子的氰基烷氧基或被1至4个碳原子的烷基取代的氨基; A表示具有1至4个碳原子的烷基，B表示嘌呤-9-基，2-氧代嘧啶-1-基，取代的嘌呤-9-基或取代的2-氧代嘧啶-1-基，具有α取代基，所述α取代基选自羟基（可能被保护），具有1至4个碳原子的烷氧基，巯基（可能被保护），具有1至4个碳原子的烷硫基，具有1至4个碳原子的烷氧基，氨基（可能被保护），可以被1至4个碳原子的烷基取代的单烷基或双烷基氨基，具有1至4个碳原子的烷基和卤原子; 或其盐。
• Oligomers containing modified pyrimidines
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP1256589A2

  公开（公告）日：2002-11-13

  An oligomer comprising at least two nucleomonomers and pharmaceutically acceptable salts thereof wherein at least one of said nucleomonomers comprises a base of formula (1) or (2): wherein each X is independently O or S; R2 is a group comprising at least one pi bond connected to the carbon atom attached to the base; Pr is (H)2 or a protecting group;    with the proviso that when at least one of said nucleomonomers of said oligomer comprises deoxyuridine 5-substituted by vinyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 1-heptenyl, 1-octenyl, 1-propynyl, 1-butynyl, 1-hexynyl, 1-heptynyl, or 1-octynyl, then the remainder of the nucleomonomers comprising said oligomer are not solely comprised of phosphodiester linked 2'-deoxyadenosine, 2'deoxyguanosine, 2'-deoxycytidine, thymidine or a combination thereof; and wherein said oligomer includes at least one unit having one of thirteen specific formulas.

  由至少两种核单体及其药学上可接受的盐组成的低聚物，其中至少一种核单体包括式 (1) 或 (2) 的碱： 其中每个 X 独立地为 O 或 S； R2 是一个基团，包含至少一个与连接到碱的碳原子相连的π键； Pr 是 (H)2 或保护基团； 1-庚炔基、1-庚炔基、1-辛炔基、1-丙炔基、1-丁炔基、1-己炔基、1-庚炔基或 1-辛炔基，则组成所述低聚物的核单体的其余部分并非仅由磷酸二酯连接的 2'-脱氧腺苷、2'-脱氧鸟苷、2'-脱氧胞苷、胸腺嘧啶或其组合组成；其中所述低聚物包括至少一个具有十三种特定公式之一的单元。
• Novel bicyclonucleoside analogues
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040143114A1

  公开（公告）日：2004-07-22

  Bicyclonucleoside analogues which exhibit anti-AIDS activity and intermediates to produce oligonucleotide analogues which have anti-sense or anti-gene activity as well as in vivo stability. Compounds of the following formula (1) or their pharmaceutically acceptable salts. 1 wherein R 1 represents a hydrogen atom or a protecting group for a hydroxy group, R 2 represents an azido group or an optionally protected amino group or the like, B represents a purin-9-yl or a 2-oxo-1,2-dihydropyrimidin-1-yl group, which are optionally substituted with substituents selected from the group consisting of a halogen atom, an alkyl group having 1-6 carbon atoms, a hydroxy group, a mercapto group and an amino group.

  具有抗艾滋病活性的双环核苷类似物，以及生产具有抗义或抗基因活性和体内稳定性的寡核苷酸类似物的中间体。下式(1)化合物或其药学上可接受的盐类。 1 其中 R 1 代表氢原子或羟基的保护基团，R 2 B 代表嘌呤-9-基或 2-氧代-1,2-二氢嘧啶-1-基，它们可选择被选自卤素原子、具有 1-6 个碳原子的烷基、羟基、巯基和氨基的取代基取代。