1-methoxy-9-oxoacridan-4-carboxylic acid | 94636-70-1

• 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: 1-methoxy-9-oxoacridan-4-carboxylic acid
• 英文别名: 1-methoxy-9-oxo-9,10-dihydroacridine-4-carboxylicacid；1-methoxy-9-oxo-10H-acridine-4-carboxylic acid
• CAS: 94636-70-1
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: ASQBSWGFQMAAAV-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：

  1-methoxy-9-oxoacridan-4-carboxylic acid 在 盐酸 、 aluminum amalgam 、 三氯化铁 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 反应 0.08h， 生成 1-Methoxy-acridine-4-carboxylic acid (2-dimethylamino-ethyl)-amide
  参考文献：
  名称：

  潜在的抗肿瘤药。50.N- [2-（二甲基氨基）乙基] ac啶-4-羧酰胺的衍生物的体内固体肿瘤活性。

  摘要：

  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。

  DOI：

  10.1021/jm00387a014
• 作为产物：
  描述：

  2-氨基-4-甲氧基苯甲酸甲酯 在 sodium hydroxide 、 polyphosphate ester 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 1-methoxy-9-oxoacridan-4-carboxylic acid
  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

文献信息

• 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：——
• The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 3. The Reaction of Methyl Anthranilates with Diphenyliodonium-2-carboxylates
  作者：Gordon W. Rewcastle、William A. Denny

  DOI：10.1055/s-1985-31165

  日期：——
• Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth
  作者：Aleksandar Putic、Lambert Stecher、Helge Prinz、Klaus Müller

  DOI：10.1016/j.ejmech.2010.04.013

  日期：2010.8

  A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth, in order to explore their potential as antipsoriatic agents. For structure activity relationship studies, the number and position of the hydroxyl groups were modified, the oxygen functions substituted or replaced, or additional functional groups were introduced into the acridone scaffold. 1,8-Dihydroxy-10H-acridin-9-one (4), which is an aza-analogue of the antipsoriatic anthralin, was only marginally active. However, 1,3-dihydroxy-substituted 5ee was the most potent acridone within this series and inhibited keratinocyte growth with an IC(50) value comparable to that of anthralin. In contrast to anthralin, nearly all members of the acridone series were devoid of radical generating properties, which were determined by their capability to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. Structures with a phenolic hydroxyl or an aromatic amine arranged ortho or para to the acridone NH group were exceptions. Also in contrast to anthralin, membrane-damaging effects as documented by the release of lactate dehydrogenase into the culture medium were not observed for acridones. (C) 2010 Elsevier Masson SAS. All rights reserved.
• REWCASTLE, G. W.;ATWELL, G. J.;CHAMBERS, D.;BAGULEY, B. C.;DENNY, W. A., J. MED. CHEM., 1986, 29, N 4, 472-477
  作者：REWCASTLE, G. W.、ATWELL, G. J.、CHAMBERS, D.、BAGULEY, B. C.、DENNY, W. A.

  DOI：——

  日期：——
• STEWART, G. M.;REWCASTLE, G. W.;DENNY, W. A., AUSTRAL. J. CHEM., 1984, 37, N 9, 1939-1950
  作者：STEWART, G. M.、REWCASTLE, G. W.、DENNY, W. A.

  DOI：——

  日期：——