3-(acetylamino)-6-aminoacridine | 74165-99-4

• 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: 3-(acetylamino)-6-aminoacridine
• 英文别名: 3-acetylamino-6-aminoacridine；monoacetylproflavine；acetylproflavine；N-(6-amino-acridin-3-yl)-acetamide；N-(6-Amino-acridin-3-yl)-acetamid；N-(6-Aminoacridin-3-YL)acetamide
• CAS: 74165-99-4
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: QMIVYOBIGWBDAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(acetylamino)-6-aminoacridine 在 盐酸 、 sodium iodide 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 3-amino-6-iodoacridine
  参考文献：
  名称：

  Unusual cellular uptake of cytotoxic 4-hydroxymethyl-3-aminoacridine

  摘要：

  Aminoacridine derivatives display interesting chemical and biological properties in the field of antitumor agents. The synthesis of 4-hydroxymethyl-3-aminoacridine and its iodo labelled analogue allows the study of cell distribution using two innovative, complementary and powerful techniques, real time fluorescence microscopy and dynamic secondary ion mass spectrometry (SIMS). All the data point to lysosomal localization of the active molecule. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.034
• 作为产物：
  描述：

  原黄素 、 乙酸酐 在 丙酸 作用下， 反应 60.0h， 以49%的产率得到3-(acetylamino)-6-aminoacridine
  参考文献：
  名称：

  N-连接寡糖的多功能分析和表征的探针。

  摘要：

  合成了一种新型的荧光探针3-（乙酰氨基）-6-氨基ac啶（AA-Ac），并研究了其在分析N-连接聚糖的皮摩尔水平中的适用性。发现AA-Ac是N-连接聚糖的极佳衍生试剂，其荧光强度至少是其前身2-氨基ac啶酮的两倍。通过正相和反相HPLC分析AA-Ac标记的聚糖。它们还适合通过MALDI-TOF质谱，自由区毛细管电泳和毛细管电泳/电喷雾电离质谱进行酶促测序和分析。

  DOI：

  10.1021/ac991268f

文献信息

• SUGAR CHAIN CONTAINING 4-POSITION HALOGENATED GALACTOSE AND APPLICATION THEREOF
  申请人：Nishimura Shin-Ichiro

  公开号：US20090018327A1

  公开（公告）日：2009-01-15

  The present invention is directed to, for example, an oligosaccharide having at an end thereof a 4-position halogenated galactose residue represented by formula (I): (wherein X represents a halogen atom, and R represents a monosaccharide, an oligosaccharide, or a carrier), a transferase inhibitor containing the oligosaccharide, and a method for inhibiting sugar chain elongation reaction in the presence of glycosyltransferase, the method including employing the inhibitor. The invention also provides a method for producing a 4-position halogenated galactose sugar nucleotide represented by formula (II): (wherein each of R 1 to R 3 represents a hydroxyl group, an acetyl group, a halogen atom, or a hydrogen atom; X represents a halogen atom; and M represents a hydrogen ion or a metal ion), wherein the method employs bacterium-derived galactokinase and bacterium-derived hexose-1-phosphate uridylyltransferase. The invention is also directed to a sugar chain containing 4-position halogenated galactose envisaged to be employed as drugs and other materials, and to applications of the compound.

  本发明涉及一种寡糖，其末端具有由公式(I)表示的4位卤代半乳糖残基：（其中X代表卤素原子，R代表单糖，寡糖或载体），含有该寡糖的转移酶抑制剂，以及在存在糖基转移酶时抑制糖链延长反应的方法，该方法包括使用该抑制剂。该发明还提供了一种生产由公式(II)表示的4位卤代半乳糖核苷酸的方法：（其中R1至R3中的每一个代表羟基、乙酰基、卤素原子或氢原子；X代表卤素原子；M代表氢离子或金属离子），该方法利用细菌来源的半乳糖激酶和细菌来源的己糖-1-磷酸尿苷转移酶。本发明还涉及一种含有4位卤代半乳糖的糖链，可用作药物和其他材料，并涉及该化合物的应用。
• METHOD OF PREPARING SUGAR CHAIN SAMPLE, SUGAR CHAIN SAMPLE, AND METHOD OF ANALYZING SUGAR CHAIN
  申请人：Shimaoka Hideyuki

  公开号：US20110089033A1

  公开（公告）日：2011-04-21

  A method of preparing a sugar chain sample, for reducing unreacted labeling reagent in a sample solution containing a labeled sugar chain, includes (process 1) a process of bringing the sample solution containing the labeled sugar chain into contact with monolithic silica, so as to allow the monolithic silica to adsorb a sugar chain component; (process 2) a process of washing the monolithic silica with a washing liquid; and (process 3) a process of bringing the monolithic silica into contact with an eluant, so as to elute the adsorbed sugar chain.

  一种制备糖链样品的方法，用于减少样品溶液中含有标记的糖链的未反应标记试剂，包括（过程1）将含有标记的糖链的样品溶液与单体硅胶接触，使单体硅胶吸附糖链成分；（过程2）用洗涤液洗涤单体硅胶；以及（过程3）将单体硅胶与洗脱剂接触，以洗脱吸附的糖链。
• Pyrrolo- and pyridoacridines
  作者：Abderrahim Wardani、Jean Lhomme

  DOI：10.1016/0040-4039(93)85058-5

  日期：1993.10

  The synthesis of 9-amino-(3H)-pyrrolo[2,3-c]acridine3 and 10-amino-benzo[b]-[1,7]phenanthroline4 starting from proflavine1 is described. NMR was used to ascertain their “angular” structure.

  描述了从黄酮1开始合成9-氨基-（3H）-吡咯并[2,3-c]]啶3和10-氨基-苯并[b]-[1,7]菲咯啉4。NMR用于确定它们的“角”结构。
• Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19
  作者：Julien Debray、Walid Zeghida、Muriel Jourdan、David Monchaud、Marie-Louise Dheu-Andries、Pascal Dumy、Marie-Paule Teulade-Fichou、Martine Demeunynck

  DOI：10.1039/b912716j

  日期：——

  The present article reports on the design and the synthesis of a series of mono- and bis-pyrimidinoacridines and their evaluation as a novel family of quadruplex-binders. It is shown that bispyrimidinoacridines represent an interesting compromise between easy synthetic access and efficiency in terms of quadruplex interaction (both affinic and selective), as judged by G4-FID assay and molecular modelling. The present study also highlights that control of the π-stacking interactions taking place between the ligand and the accessible G-tetrad of a quadruplex-DNA is indeed essential for good recognition but not exclusively (key role of direct and water-mediated H-bonds). The introduction of additional amino side chains, valuable in the acridine series, results here in steric perturbations of the ligand/quadruplex recognition and lowers the quadruplex/duplex selectivity.

  本文报道了一系列单嘧啶和双嘧啶吖啶的设计和合成，并评估了它们作为新型四联体结合剂的作用。结果表明，根据G4-FID检测和分子建模，双嘧啶吖啶在易于合成和四联体相互作用（亲和力和选择性）效率之间取得了有趣的平衡。本研究还强调，对配体与四联体DNA可及G四联体之间π堆积相互作用的控制对于良好识别确实至关重要，但并非唯一（直接和水介导的氢键的关键作用）。在吖啶系列中引入额外的氨基侧链，会导致配体/四联体识别的空间位阻，并降低四联体/双链的选择性。
• [EN] NOVEL HDMX INHIBITORS AND THEIR USE FOR CANCER TREATMENT<br/>[FR] NOUVEAUX INHIBITEURS HDMX ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：MIRX PHARMACEUTICALS LLC

  公开号：WO2015153535A1

  公开（公告）日：2015-10-08

  The present invention provides for novel acridine-like class of compounds that have demonstrated efficiency in treating cancer. The compounds of the present invention have demonstrated efficacy in binding to and antagonizing the activity of the p53 repressor, HDMX. Once administered to a cell, the compounds of the present invention bind HDMX, thereby allowing p53 to induce apoptosis of the cancerous cell. A combination of this class of compounds along with Nutlin3 provides a novel approach to treat cancers.

  本发明提供了一种新型的类似于吖啶的化合物，已经证明可以有效地治疗癌症。本发明的化合物已经证明在结合并拮抗p53抑制剂HDMX的活性方面具有疗效。一旦这些化合物被注入细胞，它们会与HDMX结合，从而使p53诱导癌细胞凋亡。将这类化合物与Nutlin3结合使用可以提供一种治疗癌症的新方法。