ethyl thieno[2,3-b]quinoline-2-carboxylate | 799833-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl thieno[2,3-b]quinoline-2-carboxylate
• CAS: 799833-64-0
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: KUCAAJKZHFZCOH-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  425.8±25.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl thieno[2,3-b]quinoline-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以72%的产率得到噻吩并[2,3-b]喹啉-2-羧酸
  参考文献：
  名称：

  新型噻吩基喹啉类β-二酮及其衍生物的合成，抗氧化和抗炎性评估

  摘要：

  在超声波作用下制备了新型的噻吩并[2,3 - b ]喹啉-2-羧酸衍生物，包括β-二酮，吡唑和黄酮，并对其体外抗氧化和抗炎活性进行了评估。用DPPH自由基清除法测定抗氧化活性，用HRBC膜稳定法测定抗炎活性。一些化合物显示出良好的抗氧化活性，而一些带有吡唑核心的化合物则显示出良好的抗炎活性。还针对合成的化合物的良好口服药物生物利用度和药物相似性，计算了进一步的计算机理化性质。

  DOI：

  10.1002/jhet.2722
• 作为产物：
  描述：

  3-formyl-2-mercaptoquinoline 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 ethyl thieno[2,3-b]quinoline-2-carboxylate
  参考文献：
  名称：

  Chemistry of Substituted Quinolines: Thieno[2,3- b ] and Thiopyrano[2,3- b ]quinolines

  摘要：

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/10426500601088846

文献信息

• Synthesis of 2-ethoxycarbonylthieno[2,3-<i>b</i>]quinolines in biomass-derived solvent γ-valerolactone and their biological evaluation against protein tyrosine phosphatase 1B
  作者：Xu-Yang Mu、Zhi-Jia Wang、Bo Feng、Lei Xu、Li-Xin Gao、Rajendran Satheeshkumar、Jia Li、Yu-Bo Zhou、Wen-Long Wang

  DOI：10.1039/d0ra09247a

  日期：——

  A series of 2-ethoxycarbonylthieno[2,3-b]quinolines were synthesized in the bio-derived “green” solvent γ-valerolactone and evaluated for their inhibitory activities against PTP1B, compound6adisplayed an IC₅₀value of 8.04 ± 0.71 μM with 4.34-fold preference over TCPTP.

  一系列2-乙氧羰基噻吩[2,3-b]喹啉类化合物在生物衍生的“绿色”溶剂γ-戊内酯中合成，并评估其对PTP1B的抑制活性，化合物6a显示出IC50值为8.04 ± 0.71 μM，对TCPTP具有4.34倍的选择性。
• Design, synthesis, in vitro, and in silico enzymatic evaluations of thieno[2,3-b]quinoline-hydrazones as novel inhibitors for α-glucosidase
  作者：Milad Noori、Mryam Rastak、Mohammad Halimi、Minoo Khalili Ghomi、Mrjan Mollazadeh、Maryam Mohammadi-Khanaposhtani、Mohammad Hosein Sayahi、Zahra Rezaei、Somayeh Mojtabavi、Mohammad Ali Faramarzi、Bagher Larijani、Mahmood Biglar、Massoud Amanlou、Mohammad Mahdavi

  DOI：10.1016/j.bioorg.2022.105996

  日期：2022.10

  9a-n by facile and efficient conventional chemical reactions. These compounds were characterized by IR, 1H NMR, 13C NMR, and elemental analysis. Inhibitory activities of the title compounds were evaluated against yeast α-glucosidase. In particular, compounds 9c, 9d, and 9h exhibited high anti-α-glucosidase activity. Representatively, compound 9c with IC50 = 1.3 µM, was 576-times more potent than positive

  在开发新型抗α-葡萄糖苷酶药物的过程中，我们通过简便有效的常规化学反应合成了新型噻吩并[2,3 - b ]喹啉-腙9a-n。这些化合物通过 IR、1 H NMR、13 C NMR 和元素分析进行​​了表征。评价了标题化合物对酵母α-葡糖苷酶的抑制活性。特别是，化合物9c、9d和9h表现出高抗α-葡萄糖苷酶活性。代表性地，化合物9c与 IC 50 = 1.3 µM，比阳性对照阿卡波糖强 576 倍。对最活跃化合物的分子对接研究表明，这些化合物在α-葡萄糖苷酶活性位点形成了重要的结合相互作用。还进行了化合物9c的分子动力学研究，并将所得结果与阿卡波糖进行了比较。还评估了化合物9c、9d和9h的计算机药物相似性特性和 ADMET 预测。这些研究表明，标题最有效的化合物可以被用作候选药物。
• Chemistry of Substituted Quinolines: Thieno[2,3-<b> <i>b</i> </b>] and Thiopyrano[2,3-<b> <i>b</i> </b>]quinolines
  作者：Balaji M. Kiran、Belalakatte P. Nandeshwarappa、Vijayavittala P. Vaidya、Kittappa M. Mahadevan

  DOI：10.1080/10426500601088846

  日期：2007.3.15

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.
• Synthesis, Antioxidant, and Anti-Inflammatory Evaluation of Novel Thiophene-Fused Quinoline Based β-Diketones and Derivatives
  作者：Pravin Mahajan、Mukesh Nikam、Ashish Asrondkar、Anil Bobade、Charansingh Gill

  DOI：10.1002/jhet.2722

  日期：2017.3

  Novel thieno[2,3‐b]quinoline‐2‐carboxylic acid derivatives including β‐diketone, pyrazole, and flavone were prepared under ultrasonication and evaluated for in vitro antioxidant and anti‐inflammatory activities. Antioxidant activity was determined by DPPH radical scavenging method and anti‐inflammatory activity by HRBC membrane stabilization method. Some of the Compounds showed good antioxidant activity

  在超声波作用下制备了新型的噻吩并[2,3 - b ]喹啉-2-羧酸衍生物，包括β-二酮，吡唑和黄酮，并对其体外抗氧化和抗炎活性进行了评估。用DPPH自由基清除法测定抗氧化活性，用HRBC膜稳定法测定抗炎活性。一些化合物显示出良好的抗氧化活性，而一些带有吡唑核心的化合物则显示出良好的抗炎活性。还针对合成的化合物的良好口服药物生物利用度和药物相似性，计算了进一步的计算机理化性质。