3-(2-phthalimidoethoxy)propyne | 204061-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-(2-phthalimidoethoxy)propyne
• 英文别名: 2-[2-(prop-2-yn-1-yloxy)ethyl]-1H-isoindole-1,3(2H)-dione；2-(2-prop-2-ynoxyethyl)isoindole-1,3-dione
• CAS: 204061-98-3
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: KYGQJMABVPNPEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-phthalimidoethoxy)propyne 、 5-iodo-2',3'-dideoxycytidine 在 四(三苯基膦)钯 、 碘化亚铜 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以57.66%的产率得到5-{3-(2-phthalamidoethoxy)-propyn-1-yl}-2',3'-dideoxycytidine
  参考文献：
  名称：

  Propargylethoxyamino nucleotides

  摘要：

  本发明披露了具有以下结构的丙炔乙氧氨基核苷：##STR1## 其中，R.sub.1和R.sub.2是--H，较低的烷基或标记；B是7-脱氮嘌呤，嘌呤或嘧啶核苷碱基；W.sub.1是--H或--OH；W.sub.2是--OH或使核苷酸无法在3'-位点形成磷二酸酯键的基团；W.sub.3是--PO.sub.4，--P.sub.2 O.sub.7，--P.sub.3 O.sub.10，磷酸盐类似物或--OH。此外，提供了一种使用上述丙炔乙氧氨基核苷的引物延伸方法。

  公开号：

  US05821356A1
• 作为产物：
  描述：

  N-羟乙基酞酰亚胺 、 3-溴丙炔 在 NaH 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以36.2%的产率得到3-(2-phthalimidoethoxy)propyne
  参考文献：
  名称：

  Propargylethoxyamino nucleotides

  摘要：

  本发明披露了具有以下结构的丙炔乙氧氨基核苷：##STR1## 其中，R.sub.1和R.sub.2是--H，较低的烷基或标记；B是7-脱氮嘌呤，嘌呤或嘧啶核苷碱基；W.sub.1是--H或--OH；W.sub.2是--OH或使核苷酸无法在3'-位点形成磷二酸酯键的基团；W.sub.3是--PO.sub.4，--P.sub.2 O.sub.7，--P.sub.3 O.sub.10，磷酸盐类似物或--OH。此外，提供了一种使用上述丙炔乙氧氨基核苷的引物延伸方法。

  公开号：

  US05821356A1

文献信息

• Propargylethoxyamino nucleotide primer extensions
  申请人：The Perkin-Elmer Corporation

  公开号：US20020045180A1

  公开（公告）日：2002-04-18

  Propargylethoxyamino nucleosides are disclosed having the structure 1 wherein R 1 and R 2 are —H, lower alkyl, or label; B is a 7-deazapurine, purine, or pyrimidine nucleoside base; W 1 is —H or —OH; W 2 is —OH or a moiety which renders the nucleoside incapable of forming a phosphodiester bond at the 3′-position; and W 3 is —PO 4 , —P 2 O 7 , —P 3 O 10 , phosphate analog, or —OH. Additionally, a primer extension method is provided employing the above propargylethoxyamino nucleosides.

  本文披露了具有以下结构的丙炔乙氧氨基核苷：其中R1和R2为—H、低碳基或标记；B为7-脱氮嘌呤、嘌呤或嘧啶核苷碱基；W1为—H或—OH；W2为—OH或一种使核苷酸无法在3'-位点形成磷酸二酯键的基团；W3为—PO4、—P2O7、—P3O10、磷酸盐类似物或—OH。此外，还提供了一种使用上述丙炔乙氧氨基核苷的引物延伸方法。
• Covalently linked oligonucleotide minor grove binder conjugates
  申请人：Microprobe

  公开号：US20020052482A1

  公开（公告）日：2002-05-02

  Minor groove binding molecules are covalently bound to oligonucleotides which in their base sequence are complementary to a target sequence of single stranded or double stranded DNA, RNA or hybrids thereof. The covalently bound oligonucleotide minor groove binder conjugates strogly bind to the target sequence of the complementary strand.

  小沟结合分子与寡核苷酸共价结合，其碱基序列与单链或双链DNA、RNA或其杂交体的目标序列互补。共价结合的寡核苷酸小沟结合物与互补链的目标序列强烈结合。
• Hybridization and mismatch discrimination using oligonucleotides conjugated to minor groove binders
  申请人：Hedgpeth Joel

  公开号：US20050064463A1

  公开（公告）日：2005-03-24

  Conjugates between a minor groove binding molecule, such as the trimer of 1,2-dihydro-(3H)-pyrrolo[3,2-e]indole-7-carboxylate (CDPI 3 ), and an oligonucleotide form unusually stable hybrids with complementary target sequences, in which the tethered CDPI 3 group resides in the minor groove of the duplex. These conjugates can be used as probes and primers. Due to their unusually high binding affinity, conjugates as short as 8-mers can be used as amplification primers with high specificity and efficiency. MGB conjugation also increases the discriminatory power of short oligonucleotides, providing enhanced detection of nucleotide sequence mismatches by short oligonucleotides. The MGB-conjugated probes and primers described herein facilitate various analytic and diagnostic procedures, such as amplification reactions, PCR, detection of single-nucleotide polymorphisms, gene hunting, differential display, fluorescence energy transfer, hydrolyzable probe assays and others; by allowing the use of shorter oligonucleotides, which have higher specificity and better discriminatory power.

  一种小沟结合分子（例如1,2-二氢-（3H）-吡咯并[3,2-e]吲哚-7-羧酸三聚体（CDPI3））与寡核苷酸之间的共轭体形成具有不寻常稳定性的杂交体，其中锚定的CDPI3基团驻留在双链的小沟中。这些共轭体可用作探针和引物。由于它们的结合亲和力异常高，因此即使是8-mer长度的共轭体也可以用作具有高特异性和高效率的扩增引物。MGB结合还增加了短寡核苷酸的鉴别能力，通过短寡核苷酸提供了更好的核苷酸序列不匹配检测。在此描述的MGB结合的探针和引物可以促进各种分析和诊断程序，例如扩增反应，PCR，单核苷酸多态性检测，基因猎取，差异显示，荧光能量转移，可水解探针测定等，通过允许使用更短的寡核苷酸，这些寡核苷酸具有更高的特异性和更好的鉴别能力。
• PROPARGYLETHOXYAMINO NUCLEOTIDES
  申请人：Khan H. Shaheer

  公开号：US20060286561A1

  公开（公告）日：2006-12-21

  Propargylethoxyamino nucleosides are disclosed having the structure wherein R 1 and R 2 are —H lower alkyl, or label; B is a 7-deazapurine, purine, or pyrimidine nucleoside base; W 1 is —H or —H; W 2 is —H or a moiety which renders the nucleoside incapable of forming a phosphodiester bond at the 3′-position; and W 3 is —PO 4 , —P 2 O 7 , —P 3 O 10 , phosphate analog, or —OH. Additionaly, a primer extension method is provided employing the above propargylethoxyamino nucleosides.

  本文揭示了具有以下结构的丙炔基乙氧基氨基核苷： 其中R1和R2是—H低碳基或标记；B是7-去氮嘌呤，嘌呤或嘧啶核苷碱基；W1是—H或—H；W2是—H或使核苷酸在3'-位点无法形成磷酸二酯键的基团；W3是—PO4，—P2O7，—P3O10，磷酸盐类似物或—OH。此外，提供了一种使用上述丙炔基乙氧基氨基核苷的引物延伸方法。
• HYBRIDIZATION AND MISMATCH DISCRIMINATION USING OLIGONUCLEOTIDES CONJUGATED TO MINOR GROOVE BINDERS
  申请人：HEDGPETH JOEL

  公开号：US20090048427A1

  公开（公告）日：2009-02-19

  Conjugates between a minor groove binding molecule, such as the trimer of 1,2-dihydro-(3H)-pyrrolo[3,2-e]indole-7-carboxylate (CDPI 3 ), and an oligonucleotide form unusually stable hybrids with complementary target sequences, in which the tethered CDPI 3 group resides in the minor groove of the duplex. These conjugates can be used as probes and primers. Due to their unusually high binding affinity, conjugates as short as 8-mers can be used as amplification primers with high specificity and efficiency. MGB conjugation also increases the discriminatory power of short oligonucleotides, providing enhanced detection of nucleotide sequence mismatches by short oligonucleotides. The MGB-conjugated probes and primers described herein facilitate various analytic and diagnostic procedures, such as amplification reactions, PCR, detection of single-nucleotide polymorphisms, gene hunting, differential display, fluorescence energy transfer, hydrolyzable probe assays and others; by allowing the use of shorter oligonucleotides, which have higher specificity and better discriminatory power.

  一种小沟结合分子（例如1,2-二氢-（3H）-吡咯并[3,2-e]吲哚-7-羧酸三聚体（CDPI3））与寡核苷酸之间的共轭体形成与互补靶序列异常稳定的杂交体，在其中，被拴在一起的CDPI3基团位于双链的小沟中。这些共轭体可用作探针和引物。由于它们的结合亲和力异常高，因此即使是长度为8个碱基的共轭体也可用作具有高特异性和效率的扩增引物。MGB共轭还增加了短寡核苷酸的鉴别能力，通过短寡核苷酸提供了更好的核苷酸序列不匹配检测。所述的MGB共轭探针和引物可促进各种分析和诊断过程，例如扩增反应，PCR，单核苷酸多态性检测，基因寻找，差异显示，荧光能量转移，可水解探针测定等；通过使用更短的寡核苷酸，从而具有更高的特异性和更好的鉴别能力。