3,3'-dimethyl-[2,2'-bithiophene]-5-carbaldehyde | 887407-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,3'-dimethyl-[2,2'-bithiophene]-5-carbaldehyde
• 英文别名: 3,3'-Dimethyl-2,2'-bithiophenyl-5-carboxaldehyde；4-methyl-5-(3-methylthiophen-2-yl)thiophene-2-carbaldehyde
• CAS: 887407-04-7
• 化学式: C₁₁H₁₀OS₂
• mdl: MFCD04116371
• 分子量: 222.332
• InChiKey: DDZAAXVYZHTAHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3'-dimethyl-[2,2'-bithiophene]-5-carbaldehyde 在 potassium hydrogensulfate 、 四(三苯基膦)钯 、 正丁基锂 、 ammonium acetate 、 四丁基溴化铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.0h， 生成 (Z)-2-cyano-3-(5'-(4-(diphenylamino)phenyl)-3,3'-dimethyl-[2,2'-bithiophen]-5-yl)acrylic acid
  参考文献：
  名称：

  The effect of cyclic thiourea functionalization and β,β′-dialkylbithiophene linker on the performance of triphenylamine dyes

  摘要：

  Four new dyes (T-C1, T-C6, S-C1 and S-C6) with beta,beta '-dialkylbithiophene as pi-linkers were synthesized and utilized in dye-sensitized solar cells (DSSCs). Compared with the reference dyes (T-C0 and AZ6) with bithiophene as pi-linkers, these dyes show blue-shifted absorption bands, and their DSSCs produce lower short-circuit current and high open-circuit voltage. These may be caused by the increase of dihedral angle between two thiophenes. On the one hand, the molecular conjugations are decreased: on the other hand, steric effect of the whole structures are increased. Compared with the triphenylamine dyes (T-C0, T-C1 and T-C6), the cyclic thiourea functionalized dyes (AZ6, S-C1 and S-C6) exhibit better photophysical and photovoltaic performances. However, the superiority of cyclic thiourea functionalization is gradually disappearing with the increased steric effect of the pi-linkers. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.04.012
• 作为产物：
  描述：

  3,3-二甲基-2,2-联硫酚 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.5h， 以92%的产率得到3,3'-dimethyl-[2,2'-bithiophene]-5-carbaldehyde
  参考文献：
  名称：

  The effect of cyclic thiourea functionalization and β,β′-dialkylbithiophene linker on the performance of triphenylamine dyes

  摘要：

  Four new dyes (T-C1, T-C6, S-C1 and S-C6) with beta,beta '-dialkylbithiophene as pi-linkers were synthesized and utilized in dye-sensitized solar cells (DSSCs). Compared with the reference dyes (T-C0 and AZ6) with bithiophene as pi-linkers, these dyes show blue-shifted absorption bands, and their DSSCs produce lower short-circuit current and high open-circuit voltage. These may be caused by the increase of dihedral angle between two thiophenes. On the one hand, the molecular conjugations are decreased: on the other hand, steric effect of the whole structures are increased. Compared with the triphenylamine dyes (T-C0, T-C1 and T-C6), the cyclic thiourea functionalized dyes (AZ6, S-C1 and S-C6) exhibit better photophysical and photovoltaic performances. However, the superiority of cyclic thiourea functionalization is gradually disappearing with the increased steric effect of the pi-linkers. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.04.012

文献信息

• Library Screening by Means of Mass Spectrometry (MS) Binding Assays-Exemplarily Demonstrated for a Pseudostatic Library Addressing γ-Aminobutyric Acid (GABA) Transporter 1 (GAT1)
  作者：Miriam Sindelar、Klaus T. Wanner

  DOI：10.1002/cmdc.201200201

  日期：2012.9

  assays as a tool for library screening is reported. For library generation, dynamic combinatorial chemistry (DCC) was used. These libraries can be screened by means of MS binding assays when appropriate measures are taken to render the libraries pseudostatic. That way, the efficiency of MS binding assays to determine ligand binding in compound screening with the ease of library generation by DCC is combined

  在本研究中，报道了质谱（MS）结合测定作为文库筛选工具的应用。对于文库生成，使用了动态组合化学（DCC）。当采取适当的措施使文库具有伪静态性时，可以通过MS结合测定法筛选这些文库。通过这种方式，结合了MS结合测定在化合物筛选中确定配体结合的效率以及DCC产生文库的简便性。以γ-氨基丁酸（GABA）转运蛋白1（GAT1）为靶标，表明了该方法的可行性，代表了GABA转运蛋白的最重要亚型。为了筛选 employed文库的使用是在靶标存在下通过使各种醛类与肼衍生物反应而生成的，肼衍生物是哌啶-3-羧酸（庚酸）（已知的GAT1抑制剂的常见片段）所描绘的。为了确保生成的文库是假静态的，请使用大量过量的菜酸衍生物。由于文库是在适合结合的缓冲液系统中生成的，并且已经存在靶标，因此可以通过MS结合测定法直接分析混合物-库生成和筛选的过程因此变得易于执行。通过反卷积鉴定的命中的结合亲和力在用通过单独合成获得的
• Novel Allosteric Ligands of γ-Aminobutyric Acid Transporter 1 (GAT1) by MS Based Screening of Pseudostatic Hydrazone Libraries
  作者：Tobias J. Hauke、Thomas Wein、Georg Höfner、Klaus T. Wanner

  DOI：10.1021/acs.jmedchem.8b01602

  日期：2018.11.21

  study describes the screening of dynamic combinatorial libraries based on nipecotic acid as core structure with substituents attached to the 5- instead of the common 1-position for the search of novel inhibitors of the GABA transporter GAT1. The generated pseudostatic hydrazone libraries included a total of nearly 900 compounds and were screened for their binding affinities toward GAT1 in competitive mass

  这项研究描述了筛选以菊苣酸为核心结构的动态组合文库的筛选方法，该结构具有取代基附着在5位而不是常见的1位上，以寻找GABA转运蛋白GAT1的新型抑制剂。生成的伪静态文库总共包含近900种化合物，并在基于竞争质谱（MS）的结合试验中筛选了它们对GAT1的结合亲和力。最高亲和力的腙表征（与顺-构型外消旋- 16gf结合和吸收实验中带有一个5-（1-萘基）呋喃-2-基残基和一个最有效的四原子间隔基）揭示了GAT1的变构相互作用，迄今为止尚无关于其他任何尼克酸衍生物的报道。因此，本文引入的5-取代的庚酸衍生物可以用作研究由GAT1介导的变构调节的GABA转运的有价值的工具，并且还可以作为新一类GAT1抑制剂的起点。
• Generation and Screening of Oxime Libraries Addressing the Neuronal GABA Transporter GAT1
  作者：Felix T. Kern、Klaus T. Wanner

  DOI：10.1002/cmdc.201402376

  日期：2015.2

  present study was to transfer the concept of library screening by MS binding assays, so far applied to pseudostatic hydrazine libraries, to static oxime libraries to screen for new potent inhibitors of mGAT1, the most abundant GABA transporter in the central nervous system that represents a validated drug target for the treatment of epilepsy. Library generation was performed by reaction of guvacine derivatives

  本研究的目的是将到目前为止已应用于假静态肼文库的MS结合测定法转移文库筛选的概念，转移至静态肟文库中以筛选新型强效抑制剂mGAT1，mGAT1是中枢神经系统中最丰富的GABA转运蛋白。代表治疗癫痫病的有效药物靶标。文库的产生是通过将具有羟胺官能度的番石榴碱衍生物与各种四种醛进行反应来进行的。稀释后，通过竞争性MS结合测定法筛选文库。解卷积实验可以识别最活跃的文库中的命中，然后将它们重新合成以进行生物学评估。这样，鉴定出一系列显示结合亲和力≥8.00（p Ki）在mGAT1，在功能性GABA吸收试验中，其中一种是迄今为止已知最有效的mGAT1抑制剂，pIC 50值为8.27±0.03。
• MS‐Based Screening of 5‐Substituted Nipecotic Acid Derived Hydrazone Libraries as Ligands of the GABA Transporter 1
  作者：Tobias J. Hauke、Georg Höfner、Klaus T. Wanner

  DOI：10.1002/cmdc.201800729

  日期：——

  A screening of compound libraries based on nipecotic acid derivatives with lipophilic residues attached to the scarcely explored 5-position of the core structure was used for the search of new inhibitors of the γ-aminobutyric acid (GABA) transporter 1 (mGAT1). The generated compound libraries, which were based on hydrazone chemistry commonly used in dynamic combinatorial chemistry but rendered pseudostatic

  筛选基于带有亲脂性残基的嗜油菌酸衍生物的化合物文库，该亲脂性残基附着在核心结构的很少探索的5位上，用于寻找γ-氨基丁酸（GABA）转运蛋白1（mGAT1）的新抑制剂。通过MS结合测定法筛选生成的化合物文库，这些文库基于动态组合化学中常用的化学，但具有假静态，可通过它们对mGAT1的结合亲和力进行筛选。用nipecotic酸衍生rac-16 h [rac-（3R，5S）-5-[（E）-2-[5-（2-苯基乙炔基）噻吩-2-基]亚甲基}肼} -1-基[哌啶-3-羧酸}-氯化钠（1/2）]，发现一个命中并评估显示出亚微摩尔效价（pKi = 6.62±0.04）和在mGAT1处的非竞争性相互作用模式。通过携带一个通过三原子间隔基连接到乳酸的5位上的5-（2-苯基乙炔基）噻吩-2-基残基，化合物rac-16 h包含了迄今为止对于这类生物活性分子而言空前的结构部分，并补充了在最近发表的一项筛选活动