N,N'-diallylacetamidine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-diallylacetamidine
• 英文别名: N,N'-bis(prop-2-enyl)ethanimidamide
• 化学式: C₈H₁₄N₂
• mdl: MFCD19228054
• 分子量: 138.213
• InChiKey: NVENWXCLHXEIKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙酰胺 、 丙烯胺 以 1,2-二氯乙烷 为溶剂， 以35%的产率得到N,N'-diallylacetamidine
  参考文献：
  名称：

  Transamidation Catalyzed by a Recoverable and Reusable PolyDMAP‐Based Hafnium Chloride and Montmorillonite KSF

  摘要：

  In this article, we described the use of an easily available polymer-based hafnium chloride and montmorillonite KSF catalyst (HfCl4/KSF-polyDMAP) in transamidation under relatively mild conditions. This metal catalyst can be easily recovered and reused in this reaction to give the corresponding amides in good yields.

  DOI：

  10.1080/00397910500297180

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。
• 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。
• Labelled oligonucleotides synthesized on solid-supports
  申请人：PE Corporation (NY)

  公开号：US20010014735A1

  公开（公告）日：2001-08-16

  Methods and compositions to label oligonucleotides and analogs directly on a solid-support having the structure 1 where S is a solid-support, A is a cleavable linker, X is a moiety with three or more attachment sites, L is a label, Y is a nucleophile, i.e. O, NH, NR or S, and P 1 is an acid cleavable protecting group are provided. The labelled solid-support is reacted in a cyclical fashion to synthesize a labelled oligonucleotide on a solid-support in the 5′ to 3′ direction, having the structure: 2 Labelled oligonucleotides are also synthesized by reacting: (i) a label reagent bearing functionality consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid, (ii) an oligonucleotide on solid support with nucleophilic functionality, and (iii) a coupling reagent, whereby an ester, amide, thioester, sulfonamide, sulfonate, phosphonate, phosphoramidate, phosphorothioate, or phosphate bond is formed. The labelling reaction may be conducted at label sites including the 5′ terminus, the 3′ terminus, a nucleobase, an internucleotide linkage, a sugar, amino, sulfide, hydroxyl, and carboxyl.

  在具有以下结构的固体载体上直接标记寡核苷酸和类似物的方法和组合物 1 其中 S 是固体支持物，A 是可裂解连接体，X 是具有三个或更多连接位点的分子，L 是标签，Y 是亲核体，即 O、NH、NR 或 S，以及 P 1 是可被酸裂解的保护基团。标记的固体支持物通过循环反应，在固体支持物上沿 5′至 3′方向合成标记的寡核苷酸，该寡核苷酸具有以下结构： 2 标记的寡核苷酸也可通过以下反应合成：(i) 具有羧酸、磺酸、膦酸或磷酸等官能团的标记试剂；(ii) 具有亲核官能团的固体支持物上的寡核苷酸；(iii) 偶联试剂，从而形成酯、酰胺、硫酯、磺酰胺、磺酸盐、膦酸盐、膦酰胺、硫代磷酸盐或磷酸键。标记反应可在标记位点进行，包括 5′末端、3′末端、核碱基、核苷酸间连接、糖、氨基、硫化物、羟基和羧基。
• Multiple-labelled oligonucleotides synthesized on solid-supports
  申请人：PE Corporation (NY)

  公开号：US20020165389A1

  公开（公告）日：2002-11-07

  Methods and compositions to label oligonucleotides and analogs directly on a solid-support having the structure 1 where S is a solid-support, A is a cleavable linker, X is a moiety with three or more attachment sites, L is a label, Y is a nucleophile, i.e. O, NH, NR or S, and P 1 is an acid cleavable protecting group are provided. The labelled solid-support is reacted in a cyclical fashion to synthesize a labelled oligonucleotide on a solid-support in the 5′ to 3′ direction, having the structure: 2 Labelled oligonucleotides are also synthesized by reacting: (i) a label reagent bearing functionality consisting of carboxylic acid, sulfonic acid, phosphonic acid, or phosphoric acid, (ii) an oligonucleotide on solid support with nucleophilic functionality, and (iii) a coupling reagent, whereby an ester, amide, thioester, sulfonamide, sulfonate, phosphonate, phosphoramidate, phosphorothioate, or phosphate bond is formed. The labelling reaction may be conducted at label sites including the 5′ terminus, the 3′ terminus, a nucleobase, an internucleotide linkage, a sugar, amino, sulfide, hydroxyl, and carboxyl.

  在具有以下结构的固体载体上直接标记寡核苷酸和类似物的方法和组合物 1 其中 S 是固体支持物，A 是可裂解连接体，X 是具有三个或更多连接位点的分子，L 是标签，Y 是亲核体，即 O、NH、NR 或 S，以及 P 1 是可被酸裂解的保护基团。标记的固体支持物通过循环反应，在固体支持物上沿 5′至 3′方向合成标记的寡核苷酸，该寡核苷酸具有以下结构： 2 标记的寡核苷酸也可通过以下反应合成：(i) 具有羧酸、磺酸、膦酸或磷酸等官能团的标记试剂；(ii) 具有亲核官能团的固体支持物上的寡核苷酸；(iii) 偶联试剂，从而形成酯、酰胺、硫酯、磺酰胺、磺酸盐、膦酸盐、膦酰胺、硫代磷酸盐或磷酸键。标记反应可在标记位点进行，包括 5′末端、3′末端、核碱基、核苷酸间连接、糖、氨基、硫化物、羟基和羧基。