2-phenylbenzo[h]quinoline-4-carboxylic acid | 5278-87-5

• 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: 2-phenylbenzo[h]quinoline-4-carboxylic acid
• 英文别名: 2-phenyl-benzo[h]quinoline-4-carboxylic acid；2-Phenyl-benzo[h]chinolin-4-carbonsaeure
• CAS: 5278-87-5
• 化学式: C₂₀H₁₃NO₂
• 分子量: 299.329
• InChiKey: DULGCYHBYNNEPB-UHFFFAOYSA-N

物化性质

• 熔点：
  294 °C
• 沸点：
  543.2±38.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenylbenzo[h]quinoline-4-carboxylic acid 在 乙醇 、 硫酸 作用下， 生成 ethyl 2-phenylbenzo[h]quinoline-4-carboxylate
  参考文献：
  名称：

  POTENTIAL ANTIMALARIALS. (2-PHENYL-7,8-BENZOQUINOLYL-4)-α-PIPERIDYLCARBINOLS¹

  摘要：

  DOI：

  10.1021/jo01157a025
• 作为产物：
  描述：

  1H-苯并[g]吲哚-2,3-二酮 、 苯乙酮 在 氢氧化钾 作用下， 生成 2-phenylbenzo[h]quinoline-4-carboxylic acid
  参考文献：
  名称：

  Borsche; Wagner-Roemmich, Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 280,284

  摘要：

  DOI：

文献信息

• Design, synthesis and biological evaluation of novel benzo- and tetrahydrobenzo-[h]quinoline derivatives as potential DNA-intercalating antitumor agents
  作者：Fatemeh Jafari、Hedyeh Baghayi、Parirokh Lavaee、Farzin Hadizadeh、Fatemeh Soltani、Hamideh Moallemzadeh、Salimeh Mirzaei、Sayyed Mohammad Aboutorabzadeh、Razieh Ghodsi

  DOI：10.1016/j.ejmech.2018.12.060

  日期：2019.2

  A new series of benzo- and tetrahydro benzo-[h]quinoline bearing a flexible (dimethylamino)ethylcarboxamide side chain was designed and synthesized as DNA-intercalating antitumor agents. The cytotoxic activity of the synthesized compounds was evaluated against four human cancer cell lines including MCF-7, A2780, C26 and A549. In general, saturated quinolines (tetrahydrobenzo[h]quinolines) exhibited

  设计并合成了一系列带有柔性（二甲基氨基）乙基羧酰胺侧链的苯并-和四氢苯并-[ h ]喹啉新系列，作为DNA嵌入抗肿瘤剂。评估了合成化合物对四种人类癌细胞系的细胞毒活性，包括MCF-7，A2780，C26和A549。通常，与其相应的不饱和喹啉（苯并[ h ]喹啉）相比，饱和喹啉（四氢苯并[ h ]喹啉）表现出更大的细胞毒性。化合物6e对所有四种人类癌细胞系均表现出明显的细胞毒性，IC 50值范围为1.86至3.91μM。所选化合物的相互作用显示出明显的细胞毒性（通过紫外和荧光光谱研究了带有小牛胸腺DNA（CT-DNA）的6b，6e，6i和6j）。一般而言，苯并[ ħ〕喹啉表现出较高的相互作用与DNA比它们相应的饱和四氢苯并[效果ħ ]喹啉。在该系列中，化合物6i表现出最大的DNA嵌入作用。使用膜联蛋白V-FITC /碘化丙锭染色法研究了大多数细胞毒性化合物（6e，6b和6i）在A549细胞中
• Synthesis and characterization of Fe3O4@SiO2@(CH2)3NH(CH2)2O2P(OH)2 and its catalytic application in the synthesis of benzo-[h]quinoline-4-carboxylic acids via a cooperative anomeric based oxidation mechanism
  作者：Fatemeh Karimi、Meysam Yarie、Mohammad Ali Zolfigol

  DOI：10.1016/j.mcat.2020.110924

  日期：2020.6

  magnetometer (VSM). The impact of Fe3O4@SiO2@(CH2)3NH(CH2)2O2P(OH)2 was carefully considered in the synthesis of benzo-[h]quinoline-4-carboxylic acids via a three component reaction of aryl aldehydes, naphtylamine, and pyrovic acid in the absence of solvent. The suggested mechanism proposed an anomeric based oxidation route for final step of the described synthesis. The described catalyst was recycled and

  本研究合成了具有磁性的新型可回收纳米催化剂Fe 3 O 4 @SiO 2 @（CH 2）3 NH（CH 2）2 O 2 P（OH）2。通过热重量分析/差热分析（​​TGA / DTA），透射电子显微镜（TEM），配备能量色散光谱（EDS）的场发射扫描电子显微镜（FESEM），元素图谱分析，傅里叶确认了新型纳米催化剂的表征变换红外（FT-IR）光谱和振动样品磁力计（VSM）。Fe 3 O 4 @SiO 2的影响通过芳基醛，萘胺和pyrovic的三组分反应合成苯并[ h ]喹啉-4-羧酸时，仔细考虑了@（CH 2）3 NH（CH 2）2 O 2 P（OH）2在无溶剂的情况下呈酸性。建议的机理为所述合成的最后步骤提出了基于端基的氧化途径。所描述的催化剂被循环使用，在六次运行后产率和反应时间没有明显降低。
• Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5′-phosphatase (SHIP)
  作者：Christopher M. Russo、Arijit A. Adhikari、Daniel R. Wallach、Sandra Fernandes、Amanda N. Balch、William G. Kerr、John D. Chisholm

  DOI：10.1016/j.bmcl.2015.09.034

  日期：2015.11

  Recently, inhibition of the SH2-containing inositol 5'-phosphatase 1 (SHIP1) has become an attractive strategy for facilitating engraftment of MHC-I mismatched bone marrow grafts, increasing the number of adult stem cells in vivo, and inducing mobilization of hematopoietic stem cells. Utilizing high-throughput screening, two quinoline small molecules (NSC13480 and NSC305787) that inhibit SHIP1 enzymatic activity were discovered. New syntheses of these inhibitors have been developed which verified the relative stereochemistry of these structures. Utilizing this synthetic route, some analogs of these quinolines have been prepared and tested for their ability to inhibit SHIP. These structure activity studies determined that an amine tethered to the quinoline core is required for SHIP inhibition. SHIP inhibition may explain the antitumor effects of similar quinoline amino alcohols and provides an impetus for further synthetic studies in this class of compounds. (C) 2015 Elsevier Ltd. All rights reserved.
• Doebner; Kuntze, Justus Liebigs Annalen der Chemie, 1888, vol. 249, p. 133
  作者：Doebner、Kuntze

  DOI：——

  日期：——
• A HOFMANN TYPE REARRANGEMENT IN LIQUID AMMONIA¹
  作者：H. C. WHITE、F. W. BERGSTROM

  DOI：10.1021/jo01200a007

  日期：1942.11