9-oxo-9,10-dihydroacridine-4-carbohydrazide | 1147097-28-6

• 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: 9-oxo-9,10-dihydroacridine-4-carbohydrazide
• CAS: 1147097-28-6
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: GNCHZCLNTGSMSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.98
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-oxo-9,10-dihydroacridine-4-carbohydrazide 、 3,4,5-三甲氧基苯甲醛 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以79%的产率得到(E)-9-oxo-N'-(3,4,5-trimethoxybenzylidene)-9,10-dihydroacridine-4-carbohydrazide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel pyrido-dipyrimidines as dual topoisomerase II/FLT3 inhibitors in leukemia cells

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105752
• 作为产物：
  描述：

  4-羧基-9-茚酮 在 氯化亚砜 、 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 9-oxo-9,10-dihydroacridine-4-carbohydrazide
  参考文献：
  名称：

  rid啶酮-嘧啶杂化物-在抗性和敏感性癌细胞中的设计，合成，细胞毒性研究和分子对接研究

  摘要：

  设计具有取代的嘧啶的a啶酮的杂化系统，其目的是发现靶向癌细胞中多种机制的下一代抗癌药。通过实验室中简便的方法合成了杂合化合物，并通过NMR和质谱方法进行了表征，并筛选了针对A549（肺癌），Hela（宫颈），MCF7（乳腺癌）和MDA-MB-231（乳腺癌）细胞的细胞毒性线。化合物对细胞增殖的评估可鉴定出活性化合物11b，11d和11h对抗MCF7，MDA-MB-231和A549细胞系。用CT-DNA进行进一步的吸收滴定和凝胶电泳确定，杂化分子部分通过DNA嵌入显示出抗癌活性。用Akt激酶进行的蛋白质印迹分析的其他结果还表明，杂合化合物具有抑制Akt激酶活性并诱导凋亡的能力，而ABCC1则表明活性化合物也具有调节与ABCC1 / MRP1相关的多药耐药性（MDR）的能力。选择性Akt1激酶测定已确定11a，11b，11d和11h为潜在抑制剂。分子对接研究确定了Akt1和DNA活性位点的方向

  DOI：

  10.1016/j.ejmech.2017.08.023

文献信息

• Newly synthesized acridone derivatives targeting lung cancer: A toxicity and xenograft model study
  作者：Nilam Bhusare、Tanuja Yadav、Mukesh Nandave、Amruta Gadade、Vikas Dighe、Godefridus J. Peters、Maushmi S. Kumar、Mayur C. Yergeri

  DOI：10.1002/ddr.22212

  日期：2024.6

  unchanged. The xenograft model study demonstrated AC‐2 to be inhibiting HOP‐62 induced tumor via reduction in p‐AKT1 (Ser473) expression significantly. In immunofluorescence staining AC‐2 treated tissue section showed 2.5 fold reduction in the expression of p‐AKT1 (Ser473). Histopathology studies showed the destruction of tumor cells with increased necrosis after treatment. The study concluded that AC‐2 causes

  AKT 是非小细胞肺癌 (NSCLC) 中过度表达的靶点之一，在其进展中发挥着重要作用，并为治疗提供了一个有吸引力的靶点。 PI3K/AKT/mTOR 通路在 NSCLC 中上调。吖啶酮是一种重要的杂环化合物，可通过多种机制治疗癌症，其中包括以 AKT 作为靶点。在目前的工作中，该研究旨在通过急性和重复剂量口服毒性来评估三种吖啶酮衍生物（AC-2、AC-7和AC-26）的安全性。除此之外，我们还在肿瘤异种移植模型中检查了 pAKT 过表达及其这些衍生物的控制。急性和重复剂量毒性的结果表明，这些化合物高度安全，对大鼠没有任何毒性、死亡率或体重、食物和水摄入量的显着改变。在重复剂量毒性中，化合物在 400 mg/kg 剂量下的一些血液学参数的变化可以忽略不计。组织病理学、生化和尿液参数保持不变。异种移植模型研究表明 AC-2 通过减少 p-AKT1（Ser第473章) 表达显着。在免疫荧光染色中，AC-2
• Novel Carbohydrazide and Hydrazone Biomarkers Based on 9-Substituted Acridine and Anthracene Fluorogens
  作者：Ján Imrich、Zdenka Bedlovičová、Pavol Kristian、Ivan Danihel、Stanislav Böhm、Danica Sabolová、Mária Kožurková、Helena Paulíková、Karel D. Klika

  DOI：10.3987/com-09-s(s)83

  日期：——

  Three series of carbohydrazides or hydrazones bearing either acridine or anthracene pharmacophores were synthesized as potential noncovalent DNA-binding antitumor agents. Carbohydrazides with an acridine or anthracene moiety were prepared from appropriate acridine or anthracene carbaldehydes via cyclocondensation with selected hydrazides whilst hydrazones with a 10H-acridin-9-ylidene moiety were obtained by condensation of (acridin-9-yl)hydrazine with various aldehydes or ketones. The spectroscopic properties of the first two series revealed efficient fluorescence implying that the compounds could be amenable for use as biomarkers. The structures of the compounds were characterized by spectral methods (UV-vis, fluorescence, IR, and (1)H, (13)C, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO, and AM I). The first carbohydrazide series was also tested against human leukemia cell line HL-60 wherein the phenyl-substituted derivative was found to possess the highest activity.
• Synthesis and Properties of Novel Biologically Interesting Polycyclic 1,3,4-Oxadiazoles Containing Acridine/Acridone Moieties
  作者：Ján Imrich、Zdenka Fröhlichová、Jana Tomaščiková、Pavol Kristian、Ivan Danihel、Stanislav Böhm、Danica Sabolová、Mária Kožurková、Karel D. Klika

  DOI：10.3987/com-08-s(f)80

  日期：——

  A series of polycyclic 1,3,4-oxadiazoles bearing acridine and acridone pharmacophores were synthesized as potential noncovalent DNA-binding and antitumor agents. The synthesis of oxadiazoles with acridone moiety was performed exploring oxidative cyclization of corresponding aldimines via bromine and the acridine derivatives by cyclization of acylthiosemicarbazides with mercuric oxide. The spectroscopic properties of the compounds in the case of acridonoxadiazoles showed an efficient binding activity to DNA (K = 5.3-9.2 x 10(4) M-1), whereas the acridine analogues are suitable as biomarkers. The structure of compounds were characterized by spectral methods (UV-vis, IR, H-1, C-13, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO).
• Manzoor, Mehwish; Perveen, Shahnaz; Tauseef, Saima, Journal of the Chemical Society of Pakistan, 2017, vol. 39, # 3, p. 405 - 413
  作者：Manzoor, Mehwish、Perveen, Shahnaz、Tauseef, Saima、Jahan, Sitwat、Karim, Zahida、Karim, Aneela、Taha, Muhammad、Ismail, Nor Hadiani、Khan, Khalid Mohammed

  DOI：——

  日期：——