7-methoxy-9-acridone-4-caboxylic acid | 89459-41-6

• 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: 7-methoxy-9-acridone-4-caboxylic acid
• 英文别名: 7-methoxy-9-acridone-4-carboxylic acid；7-methoxy-9-oxo-10H-acridine-4-carboxylic acid
• CAS: 89459-41-6
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: SANFCNGEEZLMQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-methoxy-9-acridone-4-caboxylic acid 在 氯化亚砜 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 4-Acridinecarboxamide, 9-amino-N-(2-(dimethylamino)ethyl)-7-methoxy-
  参考文献：
  名称：

  Potential antitumor agents. 46. Structure-activity relationships for acridine monosubstituted derivatives of the antitumor agent N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide

  摘要：

  A series of monosubstituted derivatives of the new antitumor agent N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide has been prepared, bearing methyl, methoxy, and chloro groups at available acridine positions. The physicochemical properties and antitumor activity of these compounds varied more with the position than with the nature of the substituent groups. The highest levels of both in vitro and in vivo antileukemic activity were shown by 5-substituted derivatives, while 7- and 8-substituted derivatives possessed the highest selectivity toward the HCT-8 human colon carcinoma line compared to the L1210 mouse leukemia line in vitro.

  DOI：

  10.1021/jm00154a008
• 作为产物：
  描述：

  2-氨基-5-甲氧基苯甲酸 在 N-乙基吗啉 、 sodium hydroxide 、 磷酸单乙基酯 、 水 、 铜 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 7-methoxy-9-acridone-4-caboxylic acid
  参考文献：
  名称：

  Rewcastle, Gordon W.; Denny, William A, Synthetic Communications, 1987, vol. 17, # 3, p. 309 - 318

  摘要：

  DOI：

文献信息

• Potential antitumor agents. 50. In vivo solid-tumor activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide
  作者：Graham J. Atwell、Gordon W. Rewcastle、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00387a014

  日期：1987.4

  antileukemic activity, with substituents at nearly all acridine positions proving acceptable. The compounds also show remarkable activity against the Lewis lung solid tumor in vivo, with several analogues capable of effecting 100% cures of the advanced disease. The broad SAR and high solid-tumor activity of the 9-acridine-4-carboxamides imply they should be considered as a completely new class of antitumor

  报道了一系列N- [2-（二烷基氨基）烷基] ac啶-4-羧酰胺的合成，理化性质和抗肿瘤活性。这些化合物通过插层与DNA结合，但由于弱碱性a啶发色团（pKa = 3.5-4.5）而在生理条件下以单阳离子形式存在。an啶-4-甲酰胺显示出非常广泛的抗白血病活性的结构-活性关系（SAR），几乎所有all啶位置上的取代基都被证明是可以接受的。所述化合物还具有体内抗路易斯肺实体瘤的显着活性，其几种类似物能够100％治愈晚期疾病。9-ac啶-4-羧酰胺具有宽泛的SAR和较高的固体肿瘤活性，这意味着它们应被视为一类全新的抗肿瘤药物。
• Substituted 9-aminoacridine-4-carboxamides tethered to platinum(II)diamine complexes: Chemistry, cytotoxicity and DNA sequence selectivity
  作者：Michael Carland、Martin J. Grannas、Murray J. Cairns、Vanessa J. Roknic、William A. Denny、W. David McFadyen、Vincent Murray

  DOI：10.1016/j.jinorgbio.2010.03.011

  日期：2010.8

  Three platinum complexes in which substituted (7-OMe, 9-NH2; 7-F, 9-NH2; and 7-H, 9-NH(CH2)2OH) 9-aminoacridine-4-carboxamides were tethered to a platinum(II)diamine moiety were synthesised and characterised at the chemical and biological level. These variants showed a decrease in cytotoxicity, as measured by IC50 values in HeLa cells, when compared with the parent 7-H, 9-NH2 compound. The 7-F and

  将其中取代的（7-OMe，9-NH 2 ; 7-F，9-NH 2 ;和7-H，9-NH（CH 2）2 OH）9-氨基ac啶-4-羧酰胺的三个铂络合物束缚到合成了铂（II）二胺部分，并在化学和生物学水平上进行了表征。当与亲本7-H，9-NH 2化合物相比时，这些变体显示出通过HeLa细胞中的IC 50值测量的细胞毒性降低。7-F和9-NH（CH 2）2OH取代基引起的细胞毒性下降很小，而7-OMe取代基导致的细胞毒性下降更大。研究了它们与纯化的pUC19质粒DNA的结合，发现添加7-F，9-NH（CH 2）2 OH，尤其是7-OMe取代基导致DNA结合减少。这与IC 50细胞毒性值很好地相关。但是，DNA序列的选择性不受这些部分的添加的影响。
• Stewart, Georgina M.; Rewcastle, Gordon W.; Denny, William A., Australian Journal of Chemistry, 1984, vol. 37, # 9, p. 1939 - 1950
  作者：Stewart, Georgina M.、Rewcastle, Gordon W.、Denny, William A.

  DOI：——

  日期：——
• Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides
  作者：Nerina Dodic、Bernard Dumaitre、Alain Daugan、Pascal Pianetti

  DOI：10.1021/jm00013a017

  日期：1995.6

  A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the (CHC)-C-R/5 cell line. Among them the acridone derivatives were the most potent, A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain. Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone. On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy- 9-oxo-N-[4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)ethyl]phenyl]-4-acridinecarboxamide (84) has been selected for further development.
• The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 2. The Use of 2-lodoisophthalic Acid in the Jourdan-Ullmann Reaction
  作者：Gordon W. Rewcastle、William A. Denny

  DOI：10.1055/s-1985-31164

  日期：——