2,7,7-trimethyl-5-oxo-4-(2',3',4'trimethoxyphenyl)-1,4,6,8-tetrahydroquinoline-3-carboxylic acid ethyl ester

• 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: 2,7,7-trimethyl-5-oxo-4-(2',3',4'trimethoxyphenyl)-1,4,6,8-tetrahydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl-2,7,7-trimethyl-5-oxo-4-(2,3,4-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；Ethyl 2,7,7-trimethyl-5-oxo-4-(2,3,4-trimethoxyphenyl)-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₄H₃₁NO₆
• 分子量: 429.513
• InChiKey: CHKSZORJECBQSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 5,5-二甲基-1,3-环己二酮 、 2,3,4-三甲氧基苯甲醛 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以90%的产率得到2,7,7-trimethyl-5-oxo-4-(2',3',4'trimethoxyphenyl)-1,4,6,8-tetrahydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  碘化硅作为多相催化剂的四氢喹啉的合成、表征、晶体结构和抗癌活性

  摘要：

  摘要 以碘化硅为多相催化剂高效合成四氢喹啉。据报道，乙酰乙酸乙酯、二甲酮、乙酸铵与合适的芳香醛在乙醇中。碘化硅（SiO2-I）作为一种高效的多相催化剂，可以在较短的反应时间和可重复使用的催化剂中以优异的产率提供产品。合成的 4 d 和 4 h 化合物通过单晶 X 射线衍射法表征。此外，制备的喹啉衍生物对 HepG2 和 MCF-7 细胞系显示出有效的抗癌活性。进行对接研究以评估合成化合物和标准药物阿霉素与雌激素受体 (ER) 的结合亲和力。

  DOI：

  10.1016/j.molstruc.2020.128790

文献信息

• Synthesis, characterization, crystal structure and anticancer activity of tetrahydro-quinolines using silica iodide as a heterogeneous catalyst
  作者：K.B. Ramesh、B.M. Omkaramurthy、M. Srinivas

  DOI：10.1016/j.molstruc.2020.128790

  日期：2020.12

  Abstract An efficient synthesis of tetrahydroquinolines using silica iodide as heterogeneous catalyst. Ethyl acetoacetate, dimedone, ammonium acetate with suitable aromatic aldehydes in ethanol was reported. Silica iodide (SiO2–I) acts as an efficient heterogeneous catalyst to afford the products in excellent yield in short reaction duration and reusable catalyst. The synthesized 4 d and 4 h compounds

  摘要 以碘化硅为多相催化剂高效合成四氢喹啉。据报道，乙酰乙酸乙酯、二甲酮、乙酸铵与合适的芳香醛在乙醇中。碘化硅（SiO2-I）作为一种高效的多相催化剂，可以在较短的反应时间和可重复使用的催化剂中以优异的产率提供产品。合成的 4 d 和 4 h 化合物通过单晶 X 射线衍射法表征。此外，制备的喹啉衍生物对 HepG2 和 MCF-7 细胞系显示出有效的抗癌活性。进行对接研究以评估合成化合物和标准药物阿霉素与雌激素受体 (ER) 的结合亲和力。
• Dihydropyridines as potential α-amylase and α-glucosidase inhibitors: Synthesis, in vitro and in silico studies
  作者：Hina Yousuf、Shahbaz Shamim、Khalid Mohammed Khan、Sridevi Chigurupati、Kanwal、Shehryar Hameed、Muhammad Naseem Khan、Muhammad Taha、Minhajul Arfeen

  DOI：10.1016/j.bioorg.2020.103581

  日期：2020.3

  Dihydropyridine derivatives 1-31 were synthesized via one-pot solvent free condition and screened for in vitro against alpha-amylase and alpha-glucosidase enzyme. The synthetic derivatives 1-31 showed good alpha-amylase inhibition in the range of IC50 = 2.21 +/- 0.06-9.97 +/- 0.08 mu M, as compared to the standard drug acarbose (IC50 = 2.01 +/- 0.1 mu M) and alpha-glucosidase inhibition in the range of IC50 = 2.31 +/- 0.09-9.9 +/- 0.1 mu M as compared to standard acarbose (IC50 = 2.07 +/- 0.1 mu M), respectively. To determine the mode of binding interactions of synthetic molecules with active sites of enzyme, molecular docking studies were also performed. Different spectroscopic techniques such as H-1, C-13 NMR, EI-MS, and HREI-MS were used to characterize all the synthetic compounds.
• 10.1002/aoc.7543
  作者：Rao, Adapaka Venkateswara、Maddila, Suresh、Anantha, Sai Sonali、Robert, Alice Rinky、Jonnalagadda, Sreekantha B.

  DOI：10.1002/aoc.7543

  日期：——

  This work aims to explore the catalytic potential of manganese oxide (MnO2) supported on (Fe3O4‐MWCNT) nano‐composite, which is composed of iron oxide and multi‐walled carbon nanotubes. The nano‐composite was synthesized using a simple impregnation technique. The catalyst material was extensively characterized using a variety of possible analytical methods, including X‐ray diffraction (XRD), Brunauer–Emmett–Teller (BET), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and energy dispersive X‐ray spectroscopy (EDS). Then, utilizing a multi‐component condensation protocol comprising substituted aldehydes, cyclohexadione, ethylacetoacetate, and NH4OAc, the catalytic efficacy of the Fe3O4‐MWCNT@MnO2 nano‐composite was assessed for synthesizing novel hexahydro‐quinoline analogues. The catalyst was found to be effective because of its huge specific surface area, stability, porosity, and distinctive exposed surfaces. The catalyst's surface exhibited an exceptionally active nature, as seen by the notably high turnover frequency. Herein, we present a reusable and effective catalytic method that produces outstanding product yields (93%–97%) under mild reaction conditions, using ethanol as a green solvent. Cost‐effectiveness, environmental safety, and high atom efficiency are achieved using the nano‐composite.