6-(2-thienyl)-1H-purine | 156489-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-(2-thienyl)-1H-purine
• 英文别名: 6-(2-thienyl)-9H-purine；6-thiophen-2-yl-7H-purine
• CAS: 156489-34-8
• 化学式: C₉H₆N₄S
• 分子量: 202.239
• InChiKey: ZGWXEEGHLRDDHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-thienyl)-1H-purine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 36.25h， 生成 [Ag(9-methyl-6-(thiophen-2-yl)-9H-purine)(acetonitrile)(nitrate)]_n
  参考文献：
  名称：

  6-Substituted purines containing thienyl or furyl substituents as artificial nucleobases for metal-mediated base pairing

  摘要：

  我们研究了人工核碱基 6-(2′-噻吩基)-嘌呤（6TP）和 6-(2′-呋喃基)-嘌呤（6FP）在金属介导的碱基配对中的适用性。原则上，这些核碱基应能分别提供 S、N 和 O、N 配位环境。我们以 6TP 和 6FP 的 N9-甲基化衍生物为模型核碱基，合成了两种金属配合物，并对其结构进行了表征。银（I）配合物[Ag(9-Me6TP)(CH3CN)(NO3)]n 具有聚合性质。噻吩基取代基不参与金属结合。相反，双核铜(II)配合物[Cu(9-Me6FP)Cl2(OH2)]2 则清楚地表明，呋喃取代基可以参与金属离子的配位。由 6TP:6TP 或 6FP:6FP 错配组成的寡核苷酸双螺旋在银（I）的存在下略微稳定。不过，还不能最终区分金属介导的碱基对形成和非特异性结合事件。基于这些研究，有人提出，与最初预期的沃森-克里克（Watson-Crick）型金属介导碱基对相比，胡格斯坦（Hoogsteen）型金属介导碱基对的形成应该是更有希望的选择。

  DOI：

  10.1039/c3dt51691a
• 作为产物：
  描述：

  6-氯-9-(四氢-2-吡喃基)嘌呤 在 盐酸 、 nickel dichloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 40.0h， 生成 6-(2-thienyl)-1H-purine
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of 6-Heterocyclic-Substituted Purines as Inactivation Modifiers of Cardiac Sodium Channels

  摘要：

  Purine-based analogs of SDZ 211-500 (5) were prepared and evaluated as inactivation modifiers of guinea pig or human cardiac sodium (Na) channels expressed in Xenopus oocytes. Substances which remove or slow the Na channel inactivation process in cardiac tissue are anticipated to prolong the effective refractory period and increase inotropy and thus have potential utility as antiarrhythmic agents. Heterocyclic substitution at the 6-position of the purine ring resulted in compounds with increased Na activity and potency, with 5-membered heterocycles being optimal. Only minor modifications to the benzhydrylpiperazine side chain were tolerated. Selected compounds which delayed the inactivation of Na channels were found to increase refractoriness and contractility in a rabbit Langendorff heart model, consistent with the cellular mechanism. Activity in both the oocyte and rabbit heart assays was specific to the S enantiomers. Preliminary in vivo activity has been demonstrated following intravenous infusion. The most promising compound on the basis of in vitro data is the formylpyrrole (S)-74, which is 25-fold more potent than DPI 201-106 (1) in the human heart Na channel assay.

  DOI：

  10.1021/jm00014a011

文献信息

• Aqueous-Phase Suzuki-Miyaura Cross-Coupling Reactions of Free Halopurine Bases
  作者：Michal Hocek、Petr Čapek、Milan Vrábel、Zbyněk Hasník、Radek Pohl

  DOI：10.1055/s-2006-950240

  日期：2006.10

  The Suzuki-Miyaura reaction of 9-unsubstituted 2-, 6-, and 8-halopurine bases with diverse aryl- and alkenylboronic acids in water-acetonitrile mixtures under microwave irradiation was used for the single-step synthesis of arylpurines. In most cases the product crystallized directly from the reaction mixture in high yields and good purity. The scope and limitations of these reactions were studied.

  通过水-乙腈混合物中微波辐照下，9-未取代的2-、6-和8-卤代嘌呤碱与多种芳基和烯基硼酸的Suzuki-Miyaura反应，实现了单步合成芳基嘌呤。在大多数情况下，产物以高产率直接从反应混合物中结晶，纯度良好。研究了这些反应的范围和局限性。
• Nucleoside or nucleotides having novel unnatural bases and utilization of the same
  申请人：Hirao Ichiro

  公开号：US20060263771A1

  公开（公告）日：2006-11-23

  The object of the present invention is to provide a nucleoside or nucleotide having an unnatural base. The nucleoside or nucleotide of the present invention has a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base. Preferably, the 5-position of the above base is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine; 2) an alkenyl group, an alkynyl group or an amino group, or a derivative thereof; 3) biotin or a derivative thereof; and 4) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, tetramethyl-6-carboxyrhodamine, and derivatives thereof.

  本发明的目的是提供一种具有非天然碱基的核苷或核苷酸。本发明的核苷或核苷酸具有5-取代-2-氧代（1H）-吡啶-3-基团作为碱基。优选地，上述碱基的5位被取代为以下群组中选择的取代基：1）光敏反应基团，选择自碘和溴；2）烯基基团，炔基基团或氨基基团或其衍生物；3）生物素或其衍生物；和4）荧光分子，选择自荧光素，6-羧基荧光素，四甲基-6-羧基罗丹明和其衍生物。
• METHOD FOR REPLICATING NUCLEIC ACIDS AND NOVEL UNNATURAL BASE PAIRS
  申请人：Hirao Ichiro

  公开号：US20100036111A1

  公开（公告）日：2010-02-11

  The present invention relates to a method for nucleic acid replication and novel artificial base pairs. The method of the present invention for nucleic acid replication is characterized in that a deoxyribonucleoside 5′-triphosphate, in which the hydroxyl group of phosphoric acid at the γ-position is substituted with a group selected from the group consisting of an amino group, a methylamino group, a dimethylamino group, a mercapto group and a fluoro group, is used as a substrate during replication reaction. The novel artificial base pairs of the present invention are characterized in that 7-(2-thienyl)-imidazo[4,5-b]pyridine (Ds) or an analog thereof forms a base pair with pyrrole-2-carbaldehyde (Pa) or an analog thereof.

  本发明涉及一种核酸复制方法和新型人工碱基对。本发明的核酸复制方法的特征在于，在复制反应过程中使用一种脱氧核苷酸5'-三磷酸作为底物，其中磷酸γ-位置的羟基被从以下群组中选择的一种群组所取代，所述群组包括氨基、甲基氨基、二甲基氨基、巯基和氟基。本发明的新型人工碱基对的特征在于，7-(2-噻吩基)-咪唑并[4,5-b]吡啶（Ds）或其类似物与吡咯-2-甲醛（Pa）或其类似物形成一对碱基。
• NOVEL DNA CAPABLE OF BEING AMPLIFIED BY PCR WITH HIGH SELECTIVITY AND HIGH EFFICIENCY
  申请人：Hirao Ichiro

  公开号：US20110053782A1

  公开（公告）日：2011-03-03

  The present invention relates to unnatural base pairs of Ds (a 5-amino-7-(2-thienyl)-3H-imidazo[4,5-b]pyridine-3-yl group) and a Pa derivative (a 2-nitro-1H-pyrrole-1-yl group bearing a substituent having a π-electron system attached at position 4) that can be replicated with high selectivity/high efficiency, and methods for replicating nucleic acids containing the unnatural base pairs. The present invention also relates to methods for incorporating an unnatural base bearing a functional substituent attached thereto into DNA by a nucleic acid replication reaction. The present invention also relates to methods for replicating and selectively collecting a nucleic acid containing an unnatural base pair from a nucleic acid pool. The present invention also relates to methods for determining a sequence of natural bases in the proximity of an unnatural base in DNA for achieving highly efficient and highly selective replication of a nucleic acid containing the unnatural base.

  本发明涉及Ds不自然碱基对（一种含有5-氨基-7-（2-噻吩基）-3H-咪唑[4,5-b]吡啶-3-基团的化合物）和Pa衍生物（一种2-硝基-1H-吡咯烷-1-基团，其在4位带有π电子体系的取代基）的高选择性/高效率复制，以及包含这些不自然碱基对的核酸的复制方法。本发明还涉及通过核酸复制反应将带有功能性取代基的不自然碱基引入DNA的方法。本发明还涉及从核酸池中复制和选择性收集含有不自然碱基对的核酸的方法。本发明还涉及确定DNA中不自然碱基附近自然碱基的序列以实现高效和高选择性复制含有不自然碱基的核酸的方法。
• NOVEL NUCLEOSIDE OR NUCLEOTIDE DERIVATIVE AND USE THEREOF
  申请人：Riken

  公开号：EP1816130A1

  公开（公告）日：2007-08-08

  The object of the present invention is to provide a nucleoside or nucleotide having a 5-substituted-2-oxo(1H)pyridin-3-yl group as a base, as well as a method using the same. In one embodiment, the nucleoside or nucleotide of the present invention has a fluorescent dye selected from the group consisting of 5-FAM, 6-FAM, 5-TAMRA, 6-TAMRA, DANSYL, 5-HEX, 6-HEX, 5-TET, 6-TET, 5-ROX and 6-ROX or a quencher dye selected from the group consisting of DABCYL. BHQ1 and BHQ2, which is attached either directly or through a linker to the 5-position of the above base.

  本发明的目的是提供一种以5-取代-2-氧代(1H)吡啶-3-基团为碱基的核苷或核苷酸，以及使用这种核苷或核苷酸的方法。 在一个实施方案中，本发明的核苷或核苷酸具有选自 5-FAM、6-FAM、5-TAMRA、6-TAMRA、DANSYL、5-HEX、6-HEX、5-TET、6-TET、5-ROX 和 6-ROX 组成的组的荧光染料或选自 DABCYL.BHQ1 和 BHQ2，它们直接或通过连接体连接到上述碱基的 5 位。