6-溴-2-吡啶-3-基喹啉-4-羧酸 | 5109-99-9

• 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
• 中文名称: 6-溴-2-吡啶-3-基喹啉-4-羧酸
• 中文别名: 6-溴-2-吡啶-3-基-喹啉-4-羧酸
• 英文名称: 6-Brom-4-carboxy-2-pyridyl-(3)-chinolin
• 英文别名: 6-bromo-2-pyridin-3-yl-quinoline-4-carboxylic acid；6-Bromo-2-pyridin-3-ylquinoline-4-carboxylic acid
• CAS: 5109-99-9
• 化学式: C₁₅H₉BrN₂O₂
• mdl: MFCD00206126
• 分子量: 329.153
• InChiKey: AVLAIBAXSCQGEN-UHFFFAOYSA-N

物化性质

• 熔点：
  305-307 °C
• 沸点：
  526.8±50.0 °C(Predicted)
• 密度：
  1.613±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-溴-2-吡啶-3-基喹啉-4-羧酸 在 氯化亚砜 作用下， 反应 2.0h， 生成 6-Bromo-2-pyridin-3-ylquinoline-4-carbonyl chloride hydrochloride
  参考文献：
  名称：

  Cytochrome P450 2C9 Type II Binding Studies on Quinoline-4-Carboxamide Analogues

  摘要：

  CYP2C9 is a significant P450 protein responsible for drug metabolism. With the increased use of heterocyclic compounds in drug design, a rapid and efficient predrug screening of these potential type II binding compounds is essential to avoid adverse drug reactions. To understand binding modes, we use quinoline-4-carboxamide analogues to study the factors that determine the structure-activity relationships. The results of this study suggest that the more accessible pyridine with the nitrogen para to the linkage can coordinate directly with the ferric heme iron, but this is not seen for the meta or ortho isomers. The pi-cation interaction of the naphthalene moiety and Arg 108 residue may also assist in stabilizing Substrate binding within the active-site cavity. The type II substrate binding affinity is determined by the combination of steric, electrostatic, and hydrophobicity factors; meanwhile, it is enhanced by the strength of lone pair electrons coordination with the heme iron.

  DOI：

  10.1021/jm8011257
• 作为产物：
  描述：

  3-乙酰基吡啶 、 5-溴靛红 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 6-溴-2-吡啶-3-基喹啉-4-羧酸
  参考文献：
  名称：

  靶向拓扑异构酶IIB的新型喹啉衍生物的合成、分子对接及药理研究

  摘要：

  拓扑异构酶通过消除拓扑应力，在复制过程中的 DNA 链精炼中发挥着关键作用。在许多癌细胞中观察到 TOPO 酶的异常过度表达。拓扑异构酶因其在精炼 DNA 链中的关键作用而成为对抗癌细胞的一个有吸引力的靶标。拓扑异构酶的抑制会导致双链断裂，这些双链断裂的持续积累是非常致命的，最终导致细胞凋亡。化合物 4l 在筛选的乳腺癌细胞中非常有效地诱导细胞死亡，4l 消除 MDA-MB-231 和 MBA-MB-468 细胞的增殖，IC50 分别为 18.94 和 22.68 µM。 Hoechst 和 Pi 双染色显示细胞摄取碘化丙啶后，4l 可以诱导两种乳腺癌细胞凋亡。 4l 与拓扑异构酶的分子对接揭示了与 -8.39 K Cal/mol 的强相互作用，分子动力学模拟揭示了与拓扑异构酶的强疏水相互作用。

  DOI：

  10.1016/j.molstruc.2024.138519

文献信息

• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18
• [EN] SALTS OF PAROXETINE<br/>[FR] SELS DE PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2000001692A1

  公开（公告）日：2000-01-13

  Piperidine compounds, processes for preparing them, pharmaceutical compositions comprising them and their use in therapy are disclosed.
• Cytochrome P450 2C9 Type II Binding Studies on Quinoline-4-Carboxamide Analogues
  作者：Chi-Chi Peng、Jonathan L. Cape、Tom Rushmore、Gregory J. Crouch、Jeffrey P. Jones

  DOI：10.1021/jm8011257

  日期：2008.12.25

  CYP2C9 is a significant P450 protein responsible for drug metabolism. With the increased use of heterocyclic compounds in drug design, a rapid and efficient predrug screening of these potential type II binding compounds is essential to avoid adverse drug reactions. To understand binding modes, we use quinoline-4-carboxamide analogues to study the factors that determine the structure-activity relationships. The results of this study suggest that the more accessible pyridine with the nitrogen para to the linkage can coordinate directly with the ferric heme iron, but this is not seen for the meta or ortho isomers. The pi-cation interaction of the naphthalene moiety and Arg 108 residue may also assist in stabilizing Substrate binding within the active-site cavity. The type II substrate binding affinity is determined by the combination of steric, electrostatic, and hydrophobicity factors; meanwhile, it is enhanced by the strength of lone pair electrons coordination with the heme iron.
• 10.1016/j.molstruc.2024.138519
  作者：Suresh, Navyashree C.、Kumar, B.M. Anil、Preetham, Habbanakuppe D、Srinivasa, Sudhanva Muddenahalli、Ali, Mohd Sajid、Al-Lohedan, Hamad A.、Kumar, Kothanahally S. Sharath、Shivamallu, Chandan、Jain, Anisha、Rangappa, Shobith、Umashankara、Mantelingu

  DOI：10.1016/j.molstruc.2024.138519

  日期：——

  DNA strands during the replication process by reliving the topological stress. Aberrant over expression of TOPO enzymes have been observed in many cancer cells. Topoisomerase has been an attractive target to fight against cancer cells due to its critical role in refining the DNA strands. Inhibition of topoisomerase leads to double strand break, persistent accumulation of these double strand breaks are

  拓扑异构酶通过消除拓扑应力，在复制过程中的 DNA 链精炼中发挥着关键作用。在许多癌细胞中观察到 TOPO 酶的异常过度表达。拓扑异构酶因其在精炼 DNA 链中的关键作用而成为对抗癌细胞的一个有吸引力的靶标。拓扑异构酶的抑制会导致双链断裂，这些双链断裂的持续积累是非常致命的，最终导致细胞凋亡。化合物 4l 在筛选的乳腺癌细胞中非常有效地诱导细胞死亡，4l 消除 MDA-MB-231 和 MBA-MB-468 细胞的增殖，IC50 分别为 18.94 和 22.68 µM。 Hoechst 和 Pi 双染色显示细胞摄取碘化丙啶后，4l 可以诱导两种乳腺癌细胞凋亡。 4l 与拓扑异构酶的分子对接揭示了与 -8.39 K Cal/mol 的强相互作用，分子动力学模拟揭示了与拓扑异构酶的强疏水相互作用。