4,5,6,7-tetrahydro-1-benzothiophene-2-carbohydrazide | 65361-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4,5,6,7-tetrahydro-1-benzothiophene-2-carbohydrazide
• 英文别名: 4,5,6,7-tetrahydrobenzo[b]thiophene-2-carbohydrazide
• CAS: 65361-27-5
• 化学式: C₉H₁₂N₂OS
• mdl: MFCD04969092
• 分子量: 196.273
• InChiKey: SDFUELDJXIFNSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  83.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 4,5,6,7-tetrahydro-1-benzothiophene-2-carbohydrazide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以66%的产率得到potassium 2-(4,5,6,7-tetrahydro-1-benzothien-2-ylcarbonyl)hydrazinecarbodithionate
  参考文献：
  名称：

  Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells

  摘要：

  Novel derivatives of 4,5-substituted-1,2,4-triazole-thiones and 2,5-substituted-1,3,4-thiadiazoles were synthesized and evaluated for their cytotoxicity. The biological study indicated that compounds 4-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 13, N-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-1,3,4-thiadiazol-2-amine 16, 4-amino-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2, 4-dihydro-3H-1,2,4-triazole-3-thione 20 and 4-amino-5-(5-phenylthien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 21 possessed high cytotoxicity in vitro against thymocytes, The corresponding IC50 values were 0.46 mu M, 5.2 x 10(-6) mu M, 0.012 mu M and 1.0 x 10(-6) mu M. Most toxic against lymphocytes was compound 21, IC50 - 0.012 mu M. The tested compounds showed a general stimulation effect on B-cells' response. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.006
• 作为产物：
  描述：

  4,5,6,7-四氢苯并[b]噻吩-2-羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以85%的产率得到4,5,6,7-tetrahydro-1-benzothiophene-2-carbohydrazide
  参考文献：
  名称：

  Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells

  摘要：

  Novel derivatives of 4,5-substituted-1,2,4-triazole-thiones and 2,5-substituted-1,3,4-thiadiazoles were synthesized and evaluated for their cytotoxicity. The biological study indicated that compounds 4-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 13, N-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-1,3,4-thiadiazol-2-amine 16, 4-amino-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2, 4-dihydro-3H-1,2,4-triazole-3-thione 20 and 4-amino-5-(5-phenylthien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 21 possessed high cytotoxicity in vitro against thymocytes, The corresponding IC50 values were 0.46 mu M, 5.2 x 10(-6) mu M, 0.012 mu M and 1.0 x 10(-6) mu M. Most toxic against lymphocytes was compound 21, IC50 - 0.012 mu M. The tested compounds showed a general stimulation effect on B-cells' response. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.006

文献信息

• A combinatorial approach for the discovery of drug-like inhibitors of 15-lipoxygenase-1
  作者：Ramon van der Vlag、Hao Guo、Uladzislau Hapko、Nikolaos Eleftheriadis、Leticia Monjas、Frank J. Dekker、Anna K.H. Hirsch

  DOI：10.1016/j.ejmech.2019.04.021

  日期：2019.7

  Human 15-lipoxygenase-1 (15-LOX-1) is a mammalian lipoxygenase which plays an important regulatory role in several CNS and inflammatory lung diseases. To further explore the role of this enzyme in drug discovery, novel potent inhibitors with favorable physicochemical properties are required. In order to identify such new inhibitors, we established a combinatorial screening method based on acylhydrazone

  人15-脂氧合酶-1（15-LOX-1）是一种哺乳动物的脂氧合酶，在多种中枢神经系统和炎症性肺疾病中起着重要的调节作用。为了进一步探索这种酶在药物发现中的作用，需要具有良好的理化性质的新型有效抑制剂。为了鉴定此类新抑制剂，我们建立了一种基于酰基hydr化学的组合筛选方法。这代表了组合化学的一种新应用，其重点是理化性质的提高，而不是效力的提高。这种策略使我们能够有效地筛选出44种不同酰肼的反应混合物和我们先前报道的吲哚醛核心结构，而无需单独合成所有可能的结构单元组合。我们的方法为IC提供了三种新型抑制剂在纳摩尔范围内具有50个值，并改善了亲脂性配体效率。
• Discovery of Small-Molecule Stabilizers of 14-3-3 Protein–Protein Interactions via Dynamic Combinatorial Chemistry
  作者：Alwin M. Hartman、Walid A. M. Elgaher、Nathalie Hertrich、Sebastian A. Andrei、Christian Ottmann、Anna K. H. Hirsch

  DOI：10.1021/acsmedchemlett.9b00541

  日期：2020.5.14

  small-molecule modulators, in particular stabilizers, of such complexes via traditional screening approaches is a challenging task. Herein, we pioneered the first application of dynamic combinatorial chemistry (DCC) to a PPI target, to find modulators of 14-3-3 proteins. Evaluation of the amplified hits from the DCC experiments for their binding affinity via surface plasmon resonance (SPR), revealed that the

  蛋白质-蛋白质相互作用（PPI）在许多生物过程（例如细胞周期调节和多种疾病）中起着重要作用。14-3-3蛋白家族是有吸引力的靶标，因为它们充当各种蛋白的结合伴侣，因此能够调节其生物学活性。通过传统的筛选方法发现这种复合物的小分子调节剂，特别是稳定剂是一项艰巨的任务。在此，我们率先将动态组合化学（DCC）应用于PPI目标，以发现14-3-3蛋白的调节剂。通过表面等离振子共振（SPR）对DCC实验中扩增出的命中分子的结合亲和力进行评估后发现，低微摩尔（KD 15-16μM）的酰基nes是14-3-3 /突触足蛋白PPI稳定剂。从而，
• Identification of RAD51–BRCA2 Inhibitors Using <i>N</i>-Acylhydrazone-Based Dynamic Combinatorial Chemistry
  作者：Greta Bagnolini、Beatrice Balboni、Fabrizio Schipani、Dario Gioia、Marina Veronesi、Francesca De Franco、Cansu Kaya、Ravindra P. Jumde、Jose Antonio Ortega、Stefania Girotto、Anna K. H. Hirsch、Marinella Roberti、Andrea Cavalli

  DOI：10.1021/acsmedchemlett.2c00063

  日期：2022.8.11

  applied for the first-time protein-templated dynamic combinatorial chemistry on RAD51 as a hit identification strategy. Upon design of N-acylhydrazone-based dynamic combinatorial libraries, RAD51 showed a clear templating effect, amplifying 19 N-acylhydrazones. Screening against the RAD51–BRCA2 protein–protein interaction via ELISA assay afforded 10 inhibitors in the micromolar range. Further 19F NMR experiments

  RAD51 是一种 ATP 依赖性重组酶，由 BRCA2 募集以通过同源重组介导 DNA 双链断裂修复，是一种有吸引力的抗癌药物靶点。在这里，我们首次在 RAD51 上申请了蛋白质模板化的动态组合化学作为命中识别策略。在设计基于N-酰基腙的动态组合文库后，RAD51 显示出明显的模板效应，可扩增 19 个N-酰基腙。通过 ELISA 测定筛选 RAD51-BRCA2 蛋白质-蛋白质相互作用，提供了 10 种微摩尔范围内的抑制剂。进一步的19 F NMR 实验表明，7可以结合 RAD51 并被 BRC4 取代，表明在 BRCA2 的同一结合口袋中存在相互作用。这些结果不仅证明了 ptDCC 可以成功地应用于全长寡聚 RAD51，而且还可以解决对鉴定小分子 PPI 抑制剂的替代策略的需求。
• Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells
  作者：Anelia Ts. Mavrova、Diana Wesselinova、Yordan A. Tsenov、Pavletta Denkova

  DOI：10.1016/j.ejmech.2008.03.006

  日期：2009.1

  Novel derivatives of 4,5-substituted-1,2,4-triazole-thiones and 2,5-substituted-1,3,4-thiadiazoles were synthesized and evaluated for their cytotoxicity. The biological study indicated that compounds 4-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 13, N-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-1,3,4-thiadiazol-2-amine 16, 4-amino-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2, 4-dihydro-3H-1,2,4-triazole-3-thione 20 and 4-amino-5-(5-phenylthien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 21 possessed high cytotoxicity in vitro against thymocytes, The corresponding IC50 values were 0.46 mu M, 5.2 x 10(-6) mu M, 0.012 mu M and 1.0 x 10(-6) mu M. Most toxic against lymphocytes was compound 21, IC50 - 0.012 mu M. The tested compounds showed a general stimulation effect on B-cells' response. (C) 2008 Elsevier Masson SAS. All rights reserved.