2-[(9-oxo-10H-acridine-4-carbonyl)amino]acetic acid

• 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-[(9-oxo-10H-acridine-4-carbonyl)amino]acetic acid
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: ZAIUWDOPMPBUPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(9-oxo-10H-acridine-4-carbonyl)amino]acetic acid 在 水 、 氯甲酸乙酯 、 三乙胺 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.0h， 生成 (9-oxo-9,10-dihydroacridine-4-carbonyl)glycyl-L-alanine
  参考文献：
  名称：

  Structural tuning of acridones for developing anticancer agents targeting dihydrofolate reductase

  摘要：

  Targeting dihydrofolate reductase, here, we report the tumor growth inhibitory activity of substituted acridones. The screening of the molecules over 60 cell line panel of human cancer cells identified (S)-oxiran-2-ylmethyl 9-oxo-9,10-dihydroacridine-4-carboxylate (19) with average GI(50) 0.3 mu M. The specificity of the compound to CCRF-CEM, MOLT-4 and SR cell lines of leukemia and SW-620, SF268, LOXIMVI, ACHN and MCF7 cancerous cells exhibiting GI(50) in the nM range was observed. C6 Glioma cells treated with compound 19 showed differentiated cell morphology and cell cycle arrest in G2/M phase. The interactions of the compound with dihydrofolate reductase were ascertained with the help of enzyme immunoassays, molecular docking and molecular dynamic studies.

  DOI：

  10.1016/j.bmcl.2019.126631
• 作为产物：
  描述：

  二苯胺-2,2’二羧酸 在 硫酸 、 氯甲酸乙酯 、 三乙胺 、 lithium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 2-[(9-oxo-10H-acridine-4-carbonyl)amino]acetic acid
  参考文献：
  名称：

  酪氨酸和10 H -acridin-9-a的拼接：在7.4-8.5的窄pH范围内开启荧光并在癌细胞内进行细胞内标记† •

  摘要：

  我们将10 H -acridin-9-one和（S）-酪氨酸修饰为3-（4-羟苯基）-2-[（9-氧代-9,10-二氢ac啶-4-羰基）氨基]丙酸（2） 。2经历了pH依赖的质子化/去质子化，并根据荧光的变化利用了该效应。分子在pH 7.5±1范围内的特征性荧光变化及其细胞渗透性使我们能够标记癌细胞。

  DOI：

  10.1039/c5md00534e

文献信息

• The bioinspired design of a reagent allows the functionalization of C_α–H of α,β-unsaturated carbonyl compounds via the Baylis–Hillman chemistry under ambient conditions
  作者：Palwinder Singh、Arun Kumar、Sukhmeet Kaur、Jagroop Kaur、Harpreet Singh

  DOI：10.1039/c5cc08830e

  日期：——

  A rationally designed reagent capable to affect alkylation at C[small alpha] of [small alpha], [small beta]-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-Bond...

  报道了合理设计的试剂，其能够影响[小α]，[小β]-不饱和羰基化合物的C [小α]处的烷基化。反应在室温下进行，没有任何添加剂。pH和H键...
• Thymidylate synthase inspired biomodel reagent for the conversion of uracil to thymine
  作者：Palwinder Singh、Arun Kumar、Sukhmeet Kaur、Amrinder Singh

  DOI：10.1039/c5cc03312h

  日期：——

  Inspired by TSase catalysis for dUMP conversion to dTMP, a biomodel reagent is developed.

  受TSase催化dUMP转化为dTMP的启发，开发了一种生物模型试剂。
• Stitching of tyrosine and 10H-acridin-9-one: turn-ON fluorescence in the narrow pH range 7.4–8.5 and intracellular labelling of cancer cells
  作者：Palwinder Singh、Arun Kumar、Sukhmeet Kaur、Amrinder Singh、Muskan Gupta、Gurcharan Kaur

  DOI：10.1039/c5md00534e

  日期：——

  We tailored 10H-acridin-9-one and (S)-tyrosine into 3-(4-hydroxyphenyl)-2-[(9-oxo-9,10-dihydroacridine-4-carbonyl) amino]propionic acid (2). 2 underwent pH dependent protonation/deprotonation and the effect was harnessed in terms of change in the fluorescence. The characteristic fluorescence change in the molecule in the pH 7.5 ± 1 range and its cell permeability allowed us to label cancer cells.

  我们将10 H -acridin-9-one和（S）-酪氨酸修饰为3-（4-羟苯基）-2-[（9-氧代-9,10-二氢ac啶-4-羰基）氨基]丙酸（2） 。2经历了pH依赖的质子化/去质子化，并根据荧光的变化利用了该效应。分子在pH 7.5±1范围内的特征性荧光变化及其细胞渗透性使我们能够标记癌细胞。
• Structural tuning of acridones for developing anticancer agents targeting dihydrofolate reductase
  作者：Harpreet Singh、Manpreet Kaur、Harpreet Kaur、Indu Sharma、Anmol Bhandari、Gurcharan Kaur、Palwinder Singh

  DOI：10.1016/j.bmcl.2019.126631

  日期：2019.10

  Targeting dihydrofolate reductase, here, we report the tumor growth inhibitory activity of substituted acridones. The screening of the molecules over 60 cell line panel of human cancer cells identified (S)-oxiran-2-ylmethyl 9-oxo-9,10-dihydroacridine-4-carboxylate (19) with average GI(50) 0.3 mu M. The specificity of the compound to CCRF-CEM, MOLT-4 and SR cell lines of leukemia and SW-620, SF268, LOXIMVI, ACHN and MCF7 cancerous cells exhibiting GI(50) in the nM range was observed. C6 Glioma cells treated with compound 19 showed differentiated cell morphology and cell cycle arrest in G2/M phase. The interactions of the compound with dihydrofolate reductase were ascertained with the help of enzyme immunoassays, molecular docking and molecular dynamic studies.