2-(thiophen-2-yl)-1H-indole-3-carbaldehyde | 5691-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(thiophen-2-yl)-1H-indole-3-carbaldehyde
• 英文别名: 2-(thiophen-2-yl)-indole-3-carbaldehyde；2-(2'-thyenyl) indole-3-carboxaldehyde；2-thiophen-2-yl-indole-3-carbaldehyde；2-(2'-Thienyl)-indol-3-carboxaldehyd；2-(Thienyl-2')-3-formylindol；2-(2-Thienyl)-1H-indole-3-carbaldehyde；2-thiophen-2-yl-1H-indole-3-carbaldehyde
• CAS: 5691-07-6
• 化学式: C₁₃H₉NOS
• mdl: MFCD11589309
• 分子量: 227.287
• InChiKey: LBOFPUXZLONTHE-UHFFFAOYSA-N

物化性质

• 熔点：
  238-239 °C
• 沸点：
  466.2±35.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(thiophen-2-yl)-1H-indole-3-carbaldehyde 在 2,4-双(苯硫基)-1,3-二硫杂-2,4-二磷杂环丁烷 2,4-二硫化物 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 2-(thiophen-2-yl)-1H-indole-3-carbothialdehyde
  参考文献：
  名称：

  2-（噻吩-2-基）-1H-吲哚作为有效的HIV-1非核苷逆转录酶抑制剂的合成，分子对接和生物学评估。

  摘要：

  设计，合成和评估新的2-（噻吩-2-基）-1H-吲哚衍生物在3位疏水取代基对HIV-1逆转录酶（RT）酶的抑制作用。使亚磷酸二烷基酯（2a-c）或亚磷酸三烷基酯（3a-c）与2-（噻吩-2-基）-1H-吲哚-3-甲醛（1）反应，得到相应的α-羟基膦酸酯加合物（7a-7c）。化合物1与吡喃基三苯基膦（4a-4c）的反应通过维蒂希机理进行，得到相应的乙烯（E，8a-c）。使醛1与合适的二烷基膦酸酯5a，b在霍纳-维蒂希反应条件下反应，同样得到化合物8b，c。另一方面，醛1与氰基亚甲基膦酸二乙酯膦酸酯（5c）反应，得到E-乙烯10和氰基乙烯基膦酸酯11的混合物。通过在干甲苯中用Lawesson试剂（LR，6a）或日本试剂（JR，6b）回流醛1，可得到硫醛12。通过评估HIV-1逆转录酶的抑制作用，化合物8b（IC50 = 2.93 nM）表现出优异的HIV-1 RT抑制作用，其效力约为依法韦伦（IC50

  DOI：

  10.1016/j.bioorg.2019.103521
• 作为产物：
  描述：

  2-噻吩-2-吲哚 生成 2-(thiophen-2-yl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  SHIVARAMA HOLLA B.; AMBEKAR S. Y., J. INDIAN CHEM. SOC. , 1974, 51, NO 11, 965-966

  摘要：

  DOI：

文献信息

• Photochemical electrocyclisation of 3-vinylindoles to pyrido[2,3-a]-, pyrido[4,3-a]- and thieno[2,3-a]-carbazoles: Design, synthesis, DNA binding and antitumor cell cytotoxicity
  作者：Thomas Lemster、Ulf Pindur、Gaelle Lenglet、Sabine Depauw、Christelle Dassi、Marie-Hélène David-Cordonnier

  DOI：10.1016/j.ejmech.2009.03.026

  日期：2009.8

  In the context of the design and synthesis of DNA ligands, some new hetarene annelated carbazoles were synthesized. As lead structure the intercalating tetracyclic systems pyrido[2,3-a]- and pyrido[4,3-a]-carbazoles and in one case a thieno[2,3-a]-carbazole were taken into account. A dialkyl amino amidic chain was introduced to the planar chromophoric system with the intent to generate minor groove

  在DNA配体的设计和合成过程中，合成了一些新的戊烯退火的咔唑。作为铅结构，考虑了插入的四环体系吡啶并[2,3- a ]-和吡啶并[4,3- a ]-咔唑，在一种情况下考虑了噻吩并[2,3- a ]-咔唑。将二烷基氨基酰胺链引入平面发色体系，目的是产生较小的凹槽结合性能。通过NCI抗肿瘤筛选检查了某些化合物的细胞毒性。此外，进行了生物物理和生化研究，以便获得有关此新系列分子的DNA结合特性和对DNA相关功能酶的抑制作用的一些信息。
• A copper(<scp>ii</scp>)-catalyzed annulative formylation of <i>o</i>-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
  作者：Balaji Ganesan、Gopal Chandru Senadi、Bing-Chun Guo、Min-Yuan Hung、Wei-Yu Lin

  DOI：10.1039/c8ra09214a

  日期：——

  developed for synthesizing multisubstituted 3-formyl indole scaffolds. This one-pot reaction proceeds through a cascade 5-endo-dig cyclization followed by formylation to construct 1,2-disubstituted 3-formyl indoles. The key aspects of this synthesis method are the broad substrate scope (with 38 examples), and well tolerating various functional groups. In addition, a detailed mechanism has been proposed, where

  在本文中，铜( II ) 催化的邻炔基苯胺与二甲基甲酰胺(DMF) 在氧气存在下的反应已被开发用于合成多取代的3-甲酰基吲哚支架。这种一锅法反应通过级联 5- endo -dig 环化然后甲酰化来构建 1,2-二取代的 3-甲酰基吲哚。这种合成方法的关键方面是广泛的底物范围（38 个例子），以及对各种官能团的耐受性。此外，还提出了一种详细的机制，其中 DMF 可以作为碳源，用于所得吲哚衍生物的原位C3 甲酰化。
• Synthesis, Antimicrobial and Antibiofilm Activities, and Molecular Docking Investigations of 2-(1H-Indol-3-yl)-1H-benzo[d]imidazole Derivatives
  作者：Elena Y. Mendogralo、Larisa Y. Nesterova、Ekaterina R. Nasibullina、Roman O. Shcherbakov、Danil A. Myasnikov、Alexander G. Tkachenko、Roman Y. Sidorov、Maxim G. Uchuskin

  DOI：10.3390/molecules28207095

  日期：——

  chemoselective synthesis of 2-(1H-indol-3-yl)-1H-benzo[d]imidazole derivatives is presented. We report on the antimicrobial activity of synthesized 2-(1H-indol-3-yl)-1H-benzo[d]imidazoles with significant activity against Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 43300 (MRSA), Mycobacterium smegmatis (mc(2)155/ATCC 700084), and Candida albicans ATCC 10231. High activity against staphylococci

  由于抗生素耐药性的增加和病原体生物膜的形成，许多细菌和真菌感染的治疗仍然是一个问题。在本文中，提出了化学选择性合成2-(1H-吲哚-3-基)-1H-苯并[d]咪唑衍生物的方法。我们报告了合成的 2-(1H-indol-3-yl)-1H-苯并[d]咪唑的抗菌活性，对金黄色葡萄球菌 ATCC 25923、金黄色葡萄球菌 ATCC 43300 (MRSA)、耻垢分枝杆菌 (mc(2) 具有显着活性。 )155/ATCC 700084) 和白色念珠菌 ATCC 10231。吲哚基苯并[d]咪唑 3ao 和 3aq（最低抑菌浓度 (MIC) < 1 µg/mL）以及 3aa 和 3ad (MIC 3.9–7.8) 对葡萄球菌具有高活性微克/毫升）。2-(1H-吲哚-3-基)-1-甲基-1H-苯并[d]咪唑 (3ag) 对耻垢分枝杆菌和白色念珠菌具有低 MIC（3.9 µg/mL 和 3.9 µg/分
• Atroposelective Synthesis of Planar‐Chiral Indoles via Carbene Catalyzed Macrocyclization
  作者：Gongming Yang、Yi He、Tianyi Wang、Zhipeng Li、Jian Wang

  DOI：10.1002/anie.202316739

  日期：2024.1.15

  atroposelective synthesis of macrocyclic planar-chiral indoles via NHC-catalyzed intramolecular macrocyclization is reported. In addition, the indole-based macrocycles bearing both planar and axial chirality have also been constructed via kinetic resolution. Importantly, these obtained planar-chiral macrocycles provide additional possibilities to develop novel catalysts or ligands, as well as new reactions.

  报道了通过 NHC 催化的分子内大环化反应选择性合成大环平面手性吲哚。此外，还通过动力学拆分构建了具有平面和轴向手性的吲哚基大环化合物。重要的是，这些获得的平面手性大环化合物为开发新型催化剂或配体以及新反应提供了额外的可能性。
• Novel 2-arylbenzothiazole DNA gyrase inhibitors: Synthesis, antimicrobial evaluation, QSAR and molecular docking studies
  作者：Iman A.Y. Ghannam、Eman A. Abd El-Meguid、Islam H. Ali、Donia H. Sheir、Ahmed M. El Kerdawy

  DOI：10.1016/j.bioorg.2019.103373

  日期：2019.12

  A series of new 2-arylbenzothiazole derivatives (4, 5, 6a-j, 7a-i and 8a,b) was synthesized and tested for their antimicrobial activity against different Gram-positive, Gram-negative bacteria and yeast using ciprofloxacin and fluconazole as positive controls for the antibacterial and antifungal activities, respectively. The target compounds showed stronger inhibitory activity against Gram-negative than Gram-positive bacteria. The minimum inhibitory concentration (MIC) values were determined for those compounds showed zone of inhibition >= 13 mm. Based on the MIC values for the tested compounds against E. coli, compounds (4, 5, 6c, 6d, 6g, 6i, 6j, 7b, 7c, 7g and 8a) were selected and tested for their E. coli gyrase inhibitory activity. The tested compounds showed moderate inhibitory activity against E. coli gyrase. Compounds 5, 6c, 6i, 6j and 7b displayed high inhibitory activity against E. coli gyrase with IC50 values below 10 mu M, however, they were less active than ciprofloxacin (E. coli gyrase IC50 = 1.14 mu M). The p-hydroxy-m-methoxy benzothiazole analogue 6c was the most active tested compound (E. coli gyrase IC50 = 4.85 mu M). Quantitative structure-activity relationship (QSAR) study was also implemented for the newly synthesized compounds. The QSAR study indicated that the structural feature that governs the anti-microbial activity for the newly synthesized benzothiazole derivatives is their structural hydrophilic-lipophilic balance what agrees with the chemical intuition where this balance governs their cellular absorption and so their antimicrobial activity. Molecular docking showed that the newly synthesized compounds possess the required structural feature for E. coli gyrase B inhibition through interaction with the key amino acids Asp73 and Gly77.