3-Amino-6-phenyl-thieno<2,3-b>pyridin-2-carbonsaeureethylester | 115919-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-Amino-6-phenyl-thieno<2,3-b>pyridin-2-carbonsaeureethylester
• 英文别名: ethyl 3-amino-6-phenylthieno[2,3-b]pyridine-2-carboxylate
• CAS: 115919-87-4
• 化学式: C₁₆H₁₄N₂O₂S
• mdl: MFCD00487126
• 分子量: 298.365
• InChiKey: RHLVCLJIDVQESM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Amino-6-phenyl-thieno<2,3-b>pyridin-2-carbonsaeureethylester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以98%的产率得到3-amino-6-phenylthieno[2,3-b]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Identification of thienopyridine carboxamides as selective binders of HIV-1 trans Activation Response (TAR) and Rev Response Element (RRE) RNAs

  摘要：

  合成、生化和结构研究了两类新型噻吩并吡啶甲酰胺衍生物，它们可以选择性地识别HIV-1 TAR和RRE RNAs。

  DOI：

  10.1039/c8ob02753f
• 作为产物：
  描述：

  1-phenyl-3-dimethylaminoprop-2-enone 在 三乙烯二胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Amino-6-phenyl-thieno<2,3-b>pyridin-2-carbonsaeureethylester
  参考文献：
  名称：

  Discovery and structure–activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

  摘要：

  Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[ 2,3-b] pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 mu M, SI > 30.3, 12b, EC50 = 3.5 mu M, SI > 28.6, 10l, EC50 = 3.9 mu M, SI > 25.6, 12o, EC50 = 4.5 mu M, SI > 22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.075

文献信息

• New thieno[2,3-b]pyridine-fused pyrimidin-4(3H)-ones as potential thymidylate synthase inhibitors: Synthesis, SAR, in vitro and in silico study
  作者：Sherif M.H. Sanad、Ahmed E.M. Mekky

  DOI：10.1016/j.molstruc.2023.135236

  日期：2023.6

  Cancer is the second leading cause of death, following cardiovascular disease. Thymidylate synthase (TS) has long been identified as a significant target for chemotherapy due to its critical role in DNA biosynthesis. New thieno[2,3-b]pyridine-fused pyrimidinones were prepared utilizing a three-component tandem protocol. One equivalent of 3-aminothieno[2,3-b]pyridine-2-carboxylate and 1.5 equivalents

  癌症是仅次于心血管疾病的第二大死因。由于其在 DNA 生物合成中的关键作用，胸苷酸合酶 (TS) 长期以来一直被确定为化疗的重要靶标。新的噻吩并 [2,3- b ] 吡啶融合嘧啶酮是使用三组分串联方案制备的。1 当量的 3-氨基噻吩并 [2,3- b ] 吡啶-2-羧酸酯和 1.5 当量的二甲基甲酰胺-二甲基缩醛在甲苯中的溶液在 110 °C 下微波照射 15 分钟。接下来，将粗烯胺溶解在二恶烷和一当量的相应芳香胺或 3-aryl-1 H中添加-吡唑-5-胺。混合物在 100 °C 下用微波照射 20-45 分钟，以 72-89% 的收率产生所需的嘧啶酮。新产品的体外细胞毒性检测表明其具有广泛的活性。吡唑连接的嘧啶酮2b和2c连接到p -Cl 和p -NO 2，​​表现出最好的细胞毒性，IC 50值分别高达 6.59 和 3.65 µM，针对 MCF-7、HEPG2 和 Caco2。还评估了2b和2c的体外TS
• Tandem synthesis and antibacterial screening of new thieno[2,3-<i>b</i>]pyridine-fused pyrimidin-4(3<i>H</i>)-ones linked to thiazole or oxazole units
  作者：Sherif M. H. Sanad、Ahmed E. M. Mekky

  DOI：10.1080/00397911.2023.2204192

  日期：2023.7.3

  yield of the target pyrimidinones. The new products showed a wide spectrum of antibacterial activity. In general, oxazole-linked pyrimidinones 2 exceeded their analogs 1 attached to thiazole units in antibacterial activity. Hybrids 2d, and 2e, with 4-(p-tolyl)oxazole and 4-(4-methoxyphenyl)oxazole units, demonstrated the best antibacterial potency among the new products with MIC/MBC values of 4.4/8

  摘要 使用三组分串联方案制备了新的两个系列的与噻唑或恶唑单元连接的噻吩并 [2,3- b ] 吡啶稠合嘧啶酮1和2 。因此，1当量的混合物。3-氨基噻吩并 [2,3- b ] 吡啶-2-羧酸盐首先用 1.5 当量进行微波照射。甲苯中的二甲基甲酰胺-二甲基缩醛在 110 °C 下保持 15 分钟。接下来，粗烯胺溶解在二恶烷和 1 当量。添加相应的基于 4-芳基唑的胺。将混合物在 100 °C 下微波加热 20-30 分钟，目标嘧啶酮的产率为 74-89%。新产品显示出广泛的抗菌活性。一般来说，恶唑连接的嘧啶酮2在抗菌活性方面超过了它们与噻唑单元相连的类似物1 。具有 4-(对甲苯基)恶唑和 4-(4-甲氧基苯基)恶唑单元的杂化物 2d 和 2e 在 MIC/MBC 值为 4.4/8.8 和 4.2/8.5 µM 的新产品中表现出最佳的抗菌效力，分别。根据 SwissADME，所有新的嘧啶酮都可以归类为类药物。
• Synthesis and characterization of 6-(aryl)-2-thioxo-1,2-dihydropyridine-3-carbonitriles
  作者：Fawzy A. Attaby、Ahmed H. El-Ghandour、Abdelwahed R. Sayed、Ashraf A. El Bassuony、Ahmed A.M. El-Reedy

  DOI：10.1080/17415993.2012.661734

  日期：2012.4.1

  In the present study, 3-aminothieno[2,3-b] pyridines, pyrido[3',2' :4,5] thieno[3,2-d]pyrimidinones, and pyrido[3',2' : 4,5]thieno[3,2-d][1,3]oxazinones were prepared via the reaction of 6-(aryl)-2-thioxo-1,2-dihydropyridine-3-carbonitriles with active-halogen-containing compounds. The structures of all the newly synthesized heterocyclic compounds were established by considering elemental analysis and spectral data.[GRAPHICS].
• Vieweg; Leistner; Bohm, Pharmazie, 1993, vol. 48, # 1, p. 26 - 30
  作者：Vieweg、Leistner、Bohm、Prantz、Wagner

  DOI：——

  日期：——
• Wagner; Vieweg; Leistner, Pharmazie, 1990, vol. 45, # 2, p. 102 - 109
  作者：Wagner、Vieweg、Leistner、Bohm、Krasselt、Hanfe ld、Prantz、Grupe

  DOI：——

  日期：——