4-methoxy-N-(2-methylquinolin-8-yl)benzamide | 898602-98-7

• 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: 4-methoxy-N-(2-methylquinolin-8-yl)benzamide
• CAS: 898602-98-7
• 化学式: C₁₈H₁₆N₂O₂
• mdl: MFCD03396793
• 分子量: 292.337
• InChiKey: OVHGMBYLKWCFHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氯一茂钛 、 4-methoxy-N-(2-methylquinolin-8-yl)benzamide 在 KH 作用下， 以 tetrahydrofuran 为溶剂， 以82%的产率得到η5-cyclopentadienyl[N-(2-methylquinolin-8-yl)-p-methoxybenzamide]titanium dichloride
  参考文献：
  名称：

  Syntheses, Characterization, and Ethylene (Co-)Polymerization Screening of Amidate Half-Titanocene Dichlorides

  摘要：

  A series of amidate half-titanocene dichlorides, Cp/TiLCl(2) [Cp' = Cp (as eta(5)-C(5)H(5)) or Cp* (as eta(5)-C(5)Me(5)), L = N-(2-methylquinolin-8-yl)-p-R-benzamides; C1: Cp' = Cp, R = OMe; C2: Cp' = Cp, R = Me; C3: Cp' = Cp, R = H; C4: Cp' = Cp, R = F; C5: Cp' = Cp, R = Cl; C6: Cp' = Cp*, R = OMe; C7: Cp' = Cp*, R = Me], have been synthesized by the stoichiometric reaction of Cp'TiCl(3) with the corresponding potassium amidates. All complexes are fully characterized by elemental and NMR analyses. The molecular structures of complexes C2 and C4 are confirmed by single-crystal X-ray diffraction, and the amidate moieties coordinate the titanium center by imino and alkoxide groups. The systems C1-C7/MAO show much higher activities toward ethylene polymerization than CpTiCl(3)/MAO or Cp*TiCl(3)/MAO systems. The procatalysts (C6 and C7) bearing a Cp* ligand exhibit higher activities than their analogues (C1-C5) containing a Cp ligand, while the amidate ligands containing electron-donating groups positively affect the catalytic behavior. Both increasing the ratio of MAO to titanium and reducing reaction temperature enhance the productivities; however, the molecular weights of the resultant polymers decrease with higher activities. Moreover, the C6/MAO system performs with high activity in the copolymerization of ethylene and 1-hexene or 1-octene.

  DOI：

  10.1021/om1000748
• 作为产物：
  描述：

  8-氨基喹哪啶 、 对甲氧基苯甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-methoxy-N-(2-methylquinolin-8-yl)benzamide
  参考文献：
  名称：

  QUINOLINES THAT MODULATE SERCA AND THEIR USE FOR TREATING DISEASE

  摘要：

  本文提供了喹啉，例如Formula I的化合物，其药物组合物，以及用于治疗、预防或缓解神经疾病、神经退行性疾病或糖尿病的一种或多种症状的方法。本文还提供了用于调节肌浆网/内质网C2+ATP酶活性的方法。

  公开号：

  US20190151303A1

文献信息

• Cobalt-Catalyzed Remote C-4 Functionalization of 8-Aminoquinoline Amides with Ethers via C–H Activation under Visible-Light Irradiation. Access to α-Heteroarylated Ether Derivatives
  作者：Tubai Ghosh、Pintu Maity、Brindaban C. Ranu

  DOI：10.1021/acs.orglett.7b03955

  日期：2018.2.16

  A cobalt-catalyzed selective remote C-4 alkylation of 8-aminoquinoline amides via C–H activation under irradiation with a CFL lamp in the presence of eosin Y at room temperature has been achieved. A series of pharmaceutically important C-4 quinoline amide-substituted ether derivatives has been obtained by this procedure. The C-4 functionalization of quinoline amides with inert ether is of much significance

  在室温下，在曙红Y存在下，在CFL灯照射下，通过C–H活化，实现了钴催化的8–氨基喹啉酰胺的远程C-4烷基化选择性。通过该程序已经获得了一系列药学上重要的C-4喹啉酰胺取代的醚衍生物。用惰性醚对喹啉酰胺进行C-4官能化具有重要意义，目前尚未见报道。
• [EN] QUINOLINES AND THEIR USE FOR TREATING ENDOPLASMIC RETICULUM STRESS-CAUSED DISEASES<br/>[FR] QUINOLÉINES ET LEUR UTILISATION POUR TRAITER LES MALADIES DUES AU STRESS DU RÉTICULUM ENDOPLASMIQUE
  申请人：CELLADON CORP

  公开号：WO2016032569A1

  公开（公告）日：2016-03-03

  Provided herein are quinolines, e.g., a compound of Formula (I) or (IB), pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of an endoplasmic reticulum stress-caused disease. Also provided herein are methods of their use for reducing endoplasmic reticulum stress and modulating the activity of a sarcoplasmic/endoplasmic reticulum Ca2+ ATPase.

  本文提供了喹啉类化合物，例如，化合物的化学式为（I）或（IB），以及其药物组合物，并用于治疗、预防或改善内质网应激引起的一种或多种疾病症状的方法。本文还提供了用于减少内质网应激并调节肌浆/内质网Ca2+ ATP酶活性的方法。
• Trimetallic yttrium N-(2-methylquinolin-8-yl)benzamides: synthesis, structure and use in ring-opening polymerization (ROP) of ε-caprolactone
  作者：Wenjuan Zhang、Shaofeng Liu、Wen-Hua Sun、Xiang Hao、Carl Redshaw

  DOI：10.1039/c2nj40711f

  日期：——

  A series of trimetallic yttrium complexes, L7Y3Cl2 [L = N-(2-methylquinolin-8-yl)-p-R-benzamides, 1: R = H; 2: R = OMe; 3: R = Me; 4: R = Cl], has been synthesized by the stoichiometric reaction of YCl3(THF)2 with the corresponding potassium amidates. All complexes have been characterized by elemental analysis and NMR spectroscopy. The molecular structure of complex 1 bearing seven amidate ligands was confirmed by single-crystal X-ray diffraction. Screening of these complexes, in the presence of BnOH, for ring-opening polymerization of caprolactone (ε-CL) revealed effective activities.

  通过 YCl3(THF)2 与相应酰胺酸钾的化学反应，合成了一系列三金属钇配合物 L7Y3Cl2 [L = N-(2-甲基喹啉-8-基)-p-R-苯甲酰胺，1：R = H；2：R = OMe；3：R = Me；4：R = Cl]。所有络合物都通过元素分析和核磁共振光谱进行了表征。单晶 X 射线衍射证实了含有七个酰胺配体的复合物 1 的分子结构。在有 BnOH 存在的情况下，对这些配合物进行筛选，发现它们对己内酰胺（δ-CL）的开环聚合具有有效的活性。
• Synthesis and Characterization of Dialkylaluminum Amidates and Their Ring-Opening Polymerization of ε-Caprolactone
  作者：Wenjuan Zhang、Youhong Wang、Ji Cao、Lin Wang、Yi Pan、Carl Redshaw、Wen-Hua Sun

  DOI：10.1021/om2008343

  日期：2011.11.28

  The stoichiometric reactions of N-(2-methylquinolin-8-yl) (R)amides (L1-L8; L1, R = Ph; L2, R = p-FPh; L3, R = p-ClPh; L4, R = p-(MeO)Ph; L5, R = o-MePh; L6, R = p-MePh; L7, R = Me; L8, R = CF3) with Me3Al afforded the corresponding dimethylaluminum amidate complexes [Me2AlL] (C1-C8). The treatment of N-(2-methylquinolin-8-yl)picolinamide (L9) with 1 or 2 equiv of Me3Al formed Me(2)AlL9 (C9) or Me(2)AlL9 center dot Me(3)A1 (C10), respectively; meanwhile, the stoichiometric reaction of L9 with iBu(3)Al gave iBu(2)AlL9 (C11). All organoaluminum amidate complexes were fully characterized by H-1/C-13 NMR spectroscopy and elemental analysis, and the unambiguous structures of complexes C2, C4, C9, and C11 were further determined by single-crystal X-ay diffraction. With the assistance of 1 equiv of BnOH, all dialkylaluminum amidate complexes showed appreciable activities toward the ring-opening polymerization of epsilon-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated.
• QUINOLINES AND THEIR USE FOR TREATING ENDOPLASMIC RETICULUM STRESS-CAUSED DISEASES
  申请人：EIGER BIOPHARMACEUTICALS, INC.

  公开号：US20170281611A1

  公开（公告）日：2017-10-05

  Provided herein are quinolines, e.g., a compound of Formula (I) or (IB), pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of an endoplasmic reticulum stress-caused disease. Also provided herein are methods of their use for reducing endoplasmic reticulum stress and modulating the activity of a sarcoplasmic/endoplasmic reticulum Ca 2+ ATPase.