benzo[c][2,7]naphthyridin-5(6H)-one | 28664-57-5

• 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: benzo[c][2,7]naphthyridin-5(6H)-one
• 英文别名: 6H-benzo[c][2,7]naphthyridin-5-one
• CAS: 28664-57-5
• 化学式: C₁₂H₈N₂O
• 分子量: 196.208
• InChiKey: HPFOEWJXDNWCTH-UHFFFAOYSA-N

物化性质

• 熔点：
  >260 °C
• 沸点：
  298.1±9.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzo[c][2,7]naphthyridin-5(6H)-one 在 三溴氧磷 作用下， 反应 3.0h， 以59%的产率得到5-bromobenzo[c][2,7]naphthyridine
  参考文献：
  名称：

  海洋吡啶并r啶生物碱脱甲基脱氧氨苄啶的全合成

  摘要：

  提出了海洋吡啶并r啶生物碱脱甲基脱氧安非他明（5）的四步全合成。该五环化合物的总收率为6.4％，仅利用两种商品结构单元烟酸乙酯和2-碘苯胺合成。最后的环化步骤是通过使用Knochel-Hauser碱（TMPMgCl·LiCl）进行定向远程环金属化，然后在分子内捕获酯基来实现的。

  DOI：

  10.1021/jo501312d
• 作为产物：
  描述：

  4-氯吡啶 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 硼酸三甲酯 、 叔丁基锂 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.58h， 生成 benzo[c][2,7]naphthyridin-5(6H)-one
  参考文献：
  名称：

  Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine

  摘要：

  The synthesis of 5-(4-pyridyl)benzo[c][2,7]naphthyridin-4-one (4), an intermediate previously employed in a total synthesis of the marine alkaloid, amphimedine (2), is reported. The route comprises the Pd-catalyzed Suzuki cross coupling of pyridylborane 21 with 2-iodoaniline to give the azabiaryl 22, which upon LDA-mediated cyclization and triflation leads to benzonaphthyridine 5. Stille cross coupling of 5 with pyridylstannane 24 affords the pyridylbenzonaphthyridine 25, which upon BBr3 treatment leads to the target molecule 4. Pyridine directed ortho metalation chemistry leading to halonicotinate ester 12 and amides 14a,b and cross coupling to benzonaphthyridinones 17, 18 (one-pot procedure) and azabiaryls 20a,b are also reported.

  DOI：

  10.1021/jo00107a004

文献信息

• Rhodium(I)-Catalyzed Aryl C–H Carboxylation of 2-Arylanilines with CO₂
  作者：Yuzhen Gao、Zhihua Cai、Shangda Li、Gang Li

  DOI：10.1021/acs.orglett.9b01105

  日期：2019.5.17

  An unprecedented Rh(I)-catalyzed, amino-group-assisted C–H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient

  在氧化还原中性条件下，开发了空前的Rh（I）催化的2-芳基苯胺与CO 2的氨基辅助CH羧基羧化反应。通过以t- BuOK为碱的膦配体促进了该反应，并且不需要使用其他强有机金属试剂。它能够将包括缺电子的杂芳烃在内的各种2-（杂）芳基苯胺有效地直接转化为各种菲啶酮。在初步的机理研究中还评估了反应的可能中间体。
• [EN] TREATMENT OF MCI AND ALZHEIMER'S DISEASE<br/>[FR] TRAITEMENT DU TCL ET DE LA MALADIE D'ALZHEIMER
  申请人：UNIV KENTUCKY RES FOUND

  公开号：WO2011142778A1

  公开（公告）日：2011-11-17

  The present invention provides, among other things, therapeutic compositions and methods that can effectively treat, slow or prevent a neurological disease (e.g., a neurodegenerative disease, e.g., mild cognitive impairment (MCI) or Alzheimer's disease (AD)), in particular, based on therapeutically effective amount of nifedipine, oxidized or nitroso nifedipine derivatives, lactam (e.g., a compound of formula (Ic) or (Ic-i), e.g., NFD- L1), thyroxine (T4), triiodothyronine (T3) and combinations thereof.

  本发明提供了治疗组合物和方法，可有效治疗、减缓或预防神经系统疾病（例如，神经退行性疾病，例如轻度认知障碍（MCI）或阿尔茨海默病（AD）），特别是基于治疗有效量的尼群地平、氧化或亚硝基尼群地平衍生物、内酰胺（例如公式（Ic）或（Ic-i）的化合物，例如NFD-L1）、甲状腺素（T4）、三碘甲状腺原氨酸（T3）及其组合物。
• Design and Synthesis of Poly ADP-ribose Polymerase-1 Inhibitors. 2. Biological Evaluation of Aza-5[<i>H</i>]-phenanthridin-6-ones as Potent, Aqueous-Soluble Compounds for the Treatment of Ischemic Injuries
  作者：Dana Ferraris、Yao-Sen Ko、Thomas Pahutski、Rica Pargas Ficco、Larisa Serdyuk、Christina Alemu、Chadwick Bradford、Tiffany Chiou、Randall Hoover、Shirley Huang、Susan Lautar、Shi Liang、Qian Lin、May X.-C Lu、Maria Mooney、Lisa Morgan、Yongzhen Qian、Scott Tran、Lawrence R. Williams、Qi Yi Wu、Jie Zhang、Yinong Zou、Vincent Kalish

  DOI：10.1021/jm030109s

  日期：2003.7.1

  A series of aza-5[H]-phenanthridin-6-ones were synthesized and evaluated as inhibitors of poly ADP-ribose polymerase-1 (PARP-1). Inhibitory potency of the unsubstituted aza-5[H]-phenanthridin-6-ones (i.e., benzonaphyhyridones) was dependent on the position of the nitrogen atom within the core structure. The A ring nitrogen analogues (7-, 8-, and 10-aza-5[H]-phenanthridin-6-ones) were an order of magnitude less potent than C ring nitrogen analogues (1-, 2-, 3-, and 4-aza-5[H]-phenanthridin-6-ones). Preliminary stroke results from 1- and 2-aza-5[H]-phenanthridin-6-one prompted structure-activity relationships to be established for several 2- and 3-substituted 1-aza-5[H]-phenanthridin-6-ones. The 2-substituted 1-aza-5[H]-phenanthridin-6-ones were designed to improve the solubility and pharmacokinetic profiles for this series of PARP-1 inhibitors. Most importantly, three compounds from this series demonstrated statistically significant protective effects in rat models of stroke and heart ischemia.
• A new, direct, and efficient synthesis of benzonaphthyridin-5-ones
  作者：Thomas Cailly、Frédéric Fabis、Sylvain Rault

  DOI：10.1016/j.tet.2006.04.030

  日期：2006.6

  Microwave-assisted Suzuki cross-coupling reaction of 2-fluorophenylboronic acid with all orthochlorocyanopyridine isomers allowed the rapid syntheses of key intermediates for anionic ring closure, which was performed using potassium hydroxide under microwave irradiation to give benzonaphthyridin-5-ones in high yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Various Substituted Benzo[c]-2,7-naphthyridines and an Approach towards the Skeleton of Meridine. Considerations about the Effect of Copper(II) Oxide
  作者：Salo Gronowitz、Patrick Björk、Johan Malm、Anna-Britta Hörnfeldt

  DOI：10.3987/com-96-s13

  日期：——