3-chloro-5-carboxy-9(10H)-acridanone | 24782-72-7

• 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-chloro-5-carboxy-9(10H)-acridanone
• 英文别名: 9-Oxo-6-chloracridon-4-carbonsaeure；6-chloro-9-oxo-10H-acridine-4-carboxylic acid
• CAS: 24782-72-7
• 化学式: C₁₄H₈ClNO₃
• 分子量: 273.675
• InChiKey: DOGXBRFRJOAJJW-UHFFFAOYSA-N

物化性质

• 熔点：
  >360 °C
• 沸点：
  501.5±50.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-chloro-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 3.5h， 生成 6-Chloro-9-(4-methanesulfonylamino-2-methoxy-phenylamino)-acridine-4-carboxylic acid methylamide
  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：

  2,4-二氯苯甲酸 在 sodium hydroxide 、 polyphosphoric ethyl ester 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 1.17h， 生成 3-chloro-5-carboxy-9(10H)-acridanone
  参考文献：
  名称：

  The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 3. The Reaction of Methyl Anthranilates with Diphenyliodonium-2-carboxylates

  摘要：

  DOI：

  10.1055/s-1985-31165

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。
• [EN] PYRAZOLO-ACRIDINE DERIVATIVES HAVING ANTITUMOUR ACTIVITY<br/>[FR] DERIVES DE PYRAZOLO-ACRIDINE A ACTIVITE ANTITUMORALE
  申请人：UNIVERSITA' DEGLI STUDI DI CAMERINO

  公开号：WO1999006405A1

  公开（公告）日：1999-02-11

  (EN) Pyrazolo-acridines and pyrazolo-pyrimidoacridines susbtituted with aminoalkyl chains, have evidenced a remarkable antitumour activity, in particular in colon tumours.(FR) La présente invention concerne des pyrazolo-acridines et des pyrazolo-pyrimidoacridines substituées par des chaînes aminoalkyle déployant une activité antitumorale remarquable, en particulier contre les tumeurs du côlon.

  Pyrazolo-acridines和pyrazolo-pyrimidoacridines，它们的氨基烷基链取代物表现出显著的抗肿瘤活性，尤其是对于结肠肿瘤。(EN)
• 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：——
• Potential antitumor agents. 46. Structure-activity relationships for acridine monosubstituted derivatives of the antitumor agent N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide
  作者：Gordon W. Rewcastle、Graham J. Atwell、David Chambers、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00154a008

  日期：1986.4

  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.