4-[[(8-羟基喹啉-7-基)-苯基甲基]氨基]苯甲酸 | 5335-97-7

• 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
• 中文名称: 4-[[(8-羟基喹啉-7-基)-苯基甲基]氨基]苯甲酸
• 英文名称: 4-(((8-hydroxyquinolin-7-yl)(phenyl)methyl)amino)benzoic acid
• 英文别名: 4-{[(8-hydroxyquinolin-7-yl)phenylmethyl]amino}benzoic acid；8-hydroxy-7-(4-carboxy-anilinobenzyl)-quinoline；NSC1011；4-{[(8-hydroxy-quinolin-7-yl)-phenyl-methyl]-amino}-benzoic acid；4-{[(8-hydroxy-[7]quinolyl)-phenyl-methyl]-amino}-benzoic acid；4-{[(8-Hydroxy-[7]chinolyl)-phenyl-methyl]-amino}-benzoesaeure；4-[[(8-Hydroxyquinolin-7-yl)-phenylmethyl]amino]benzoic acid
• CAS: 5335-97-7
• 化学式: C₂₃H₁₈N₂O₃
• 分子量: 370.408
• InChiKey: PSCFZETTYRDCRM-UHFFFAOYSA-N

物化性质

• 沸点：
  617.3±55.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  4-[[(8-羟基喹啉-7-基)-苯基甲基]氨基]苯甲酸 、 碘甲烷 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以33%的产率得到methyl 4-(((8-methoxyquinolin-7-yl)(phenyl)methyl)amino)benzoate
  参考文献：
  名称：

  8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

  摘要：

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.043
• 作为产物：
  描述：

  8-羟基喹啉 、 苯甲醛 、 对氨基苯甲酸 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以16%的产率得到4-[[(8-羟基喹啉-7-基)-苯基甲基]氨基]苯甲酸
  参考文献：
  名称：

  8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells

  摘要：

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.043

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: U: SVol.E2, 1.4, page 31 - 43
  作者：

  DOI：——

  日期：——
• Trailina, E. P.; Savich, I. A.; Zelentsov, V. V., Zhurnal Neorganicheskoi Khimii, 1960, vol. 5, p. 924 - 925
  作者：Trailina, E. P.、Savich, I. A.、Zelentsov, V. V.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ni: MVol.C1, 169, page 388 - 389
  作者：

  DOI：——

  日期：——
• Zelentsov, V. V.; Trailina, E. P.; Glushko, Yu. V., Zhurnal Neorganicheskoi Khimii, 1961, vol. 6, p. 543 - 544
  作者：Zelentsov, V. V.、Trailina, E. P.、Glushko, Yu. V.、Savich, I. A.、Spitsyn, V. I.

  DOI：——

  日期：——
• Chelate Compounds of 7-(α-Anilinobenzyl)-8-quinolinol
  作者：J. P. Phillips、A. L. Duckwall

  DOI：10.1021/ja01626a018

  日期：1955.11