3-methyl-5-carboxy-9(10H)-acridanone | 78847-67-3

• 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-methyl-5-carboxy-9(10H)-acridanone
• 英文别名: 3-methyl-9(10H)acridone-5-carboxylic acid；6-Methyl-9-oxo-9,10-dihydroacridine-4-carboxylic acid；6-methyl-9-oxo-10H-acridine-4-carboxylic acid
• CAS: 78847-67-3
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: XNDCKKLPPGXOMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-5-carboxy-9(10H)-acridanone 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 、 三氯化磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 9-[4-(methanesulfonamido)-2-methoxyanilino]-N,6-dimethylacridine-4-carboxamide
  参考文献：
  名称：

  Potential antitumor agents. Part 38. 3-Substituted 5-carboxamido derivatives of amsacrine

  摘要：

  The synthesis and biological evaluation of a series of 3-substituted 5-carboxamido derivatives of amsacrine (m-AMSA) are described. This series was developed as the result of previous quantitative structure-activity relationship (QSAR) studies of the antitumor activity of 9-anilinoacridine derivatives. In agreement with these studies, this class of compounds, possessing a variety of small nonpolar groups at the 3-position, together with very hydrophilic carboxamido groups at the 5-position, have high in vivo activity against animal leukemia models.

  DOI：

  10.1021/jm00365a013
• 作为产物：
  描述：

  2-溴-4-甲基苯甲酸 在 copper(I) oxide 、 硫酸 、 铜 、 potassium carbonate 作用下， 以 乙二醇乙醚 为溶剂， 反应 2.5h， 生成 3-methyl-5-carboxy-9(10H)-acridanone
  参考文献：
  名称：

  Potential antitumor agents. Part 38. 3-Substituted 5-carboxamido derivatives of amsacrine

  摘要：

  The synthesis and biological evaluation of a series of 3-substituted 5-carboxamido derivatives of amsacrine (m-AMSA) are described. This series was developed as the result of previous quantitative structure-activity relationship (QSAR) studies of the antitumor activity of 9-anilinoacridine derivatives. In agreement with these studies, this class of compounds, possessing a variety of small nonpolar groups at the 3-position, together with very hydrophilic carboxamido groups at the 5-position, have high in vivo activity against animal leukemia models.

  DOI：

  10.1021/jm00365a013

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。
• Compounds having antitumour properties, process for their preparation, these compounds for use as antitumour agents and pharmaceutical compositions containing them
  申请人：DEVELOPMENT FINANCE CORPORATION OF NEW ZEALAND

  公开号：EP0025705A1

  公开（公告）日：1981-03-25

  Compounds represented by the general formula in which R1 represents-CH3, -CH2CH3 or -(CH2)2 CH3; R2 represents -CONHR4, -F, -Cl, -Br, -I, -CF3, -N02, -NH2, -CH3, -OCH3 or-NHCOCH3, and R3 represents -CONHR4, -H, -CH3 or -OCH3, with the proviso that at least one of R2 and R3 represents -CONHR4; and R4 represents H, or -CH3, -CH2CH3, -(CH2)2CH3, -(CH2)3CH3 or - CH2CH(CH3)2, each optionally substituted with hydroxyl, amine and/or amide functions; and acid addition salts thereof have antitumour properties.

  由通式表示的化合物 其中 R1 代表-CH3、-CH2CH3 或-(CH2)2 CH3； R2 代表-CONHR4、-F、-Cl、-Br、-I、 -CF3、-N02、-NH2、-CH3、-OCH3 或-NHCOCH3，以及 R3 代表-CONHR4、-H、-CH3 或-OCH3，但 R2 和 R3 中至少有一个代表-CONHR4； 和 R4 代表 H、或-CH3、-CH2CH3、-(CH2)2CH3、-(CH2)3CH3 或-CH2CH(CH3)2，各自任选被羟基、胺和/或酰胺官能团取代； 及其酸加成盐具有抗肿瘤特性。
• Antitumor agents
  申请人：Bristol-Myers Company

  公开号：EP0165592A2

  公开（公告）日：1985-12-27

  Novel analogs of 4'-(9-acridinylamino)-methanesulfon- m-anisidide are provided for use as antitumor agents. Also provided is an improved method for preparing starting materials used in the production of such compounds.

  本研究提供了用作抗肿瘤药物的 4'-(9-吖啶基氨基)-甲磺酰胺的新型类似物，还提供了制备用于生产此类化合物的起始材料的改进方法。
• 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：——
• Rewcastle, Gordon W.; Denny, William A, Synthetic Communications, 1987, vol. 17, # 3, p. 309 - 318
  作者：Rewcastle, Gordon W.、Denny, William A

  DOI：——

  日期：——