5-nitro-9-oxo-9,10-dihydroacridine-4-carboxylic acid | 106589-17-7

• 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: 5-nitro-9-oxo-9,10-dihydroacridine-4-carboxylic acid
• 英文别名: 5-nitro-9-oxo-10H-acridine-4-carboxylic acid
• CAS: 106589-17-7
• 化学式: C₁₄H₈N₂O₅
• 分子量: 284.228
• InChiKey: NJWDKABVHQLHAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-nitro-9-oxo-9,10-dihydroacridine-4-carboxylic acid 生成 9-amino-N-[2-(dimethylamino)ethyl]-5-nitroacridine-4-carboxamide;dihydrochloride
  参考文献：
  名称：

  DENNY W. A.; ATWELL G. J.; REWCASTLE G. W.; BAGULEY B. C., J. MED. CHEM., 30,(1987) N 4, 658-663

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-甲氧基羰基苯胺基)-4-硝基苯甲酸 以98%的产率得到
  参考文献：
  名称：

  REWCASTLE, G. W.;DENNY, W. A., SYNTHESIS, BRD, 1985, N 2, 220-222

  摘要：

  DOI：

文献信息

• The bioinspired design of a reagent allows the functionalization of C_α–H of α,β-unsaturated carbonyl compounds via the Baylis–Hillman chemistry under ambient conditions
  作者：Palwinder Singh、Arun Kumar、Sukhmeet Kaur、Jagroop Kaur、Harpreet Singh

  DOI：10.1039/c5cc08830e

  日期：——

  A rationally designed reagent capable to affect alkylation at C[small alpha] of [small alpha], [small beta]-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-Bond...

  报道了合理设计的试剂，其能够影响[小α]，[小β]-不饱和羰基化合物的C [小α]处的烷基化。反应在室温下进行，没有任何添加剂。pH和H键...
• Thymidylate synthase inspired biomodel reagent for the conversion of uracil to thymine
  作者：Palwinder Singh、Arun Kumar、Sukhmeet Kaur、Amrinder Singh

  DOI：10.1039/c5cc03312h

  日期：——

  Inspired by TSase catalysis for dUMP conversion to dTMP, a biomodel reagent is developed.

  受TSase催化dUMP转化为dTMP的启发，开发了一种生物模型试剂。
• Potential antitumor agents. 49. 5-Substituted derivatives of N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide with in vivo solid-tumor activity
  作者：William A. Denny、Graham J. Atwell、Gordon W. Rewcastle、Bruce C. Baguley

  DOI：10.1021/jm00387a013

  日期：1987.4

  Derivatives of N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide bearing a wide variety of different groups at the 5-position (and for comparative purposes at the 7-position) have been prepared, and their physicochemical properties and biological activities have been determined. Although both 5- and 7-substituted compounds bind equally well to DNA by intercalation, only the 5-substituted compounds

  制备了N- [2-（二甲基氨基）乙基] -9-氨基ac啶-4-羧酰胺的衍生物，这些衍生物在5-位（并且为了比较起见在7-位）带有多种不同的基团，并且其理化性质性质和生物活性已经确定。尽管5-和7-取代的化合物通过插入均与DNA结合良好，但是仅5-取代的化合物具有体内抗肿瘤活性。所有5-取代的化合物均显示出体内的抗白血病活性，但只有那些具有足以确保ensure啶生色团在生理pH下不带电荷的吸电子取代基的化合物，才显示出对路易斯肺实体瘤的体内活性。弱碱性衍生物对实体瘤细胞没有更大的内在细胞毒性或选择性，
• 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.
• Chen; Deady; Baguley, Journal of Medicinal Chemistry, 1994, vol. 37, # 5, p. 593 - 597
  作者：Chen、Deady、Baguley、Denny

  DOI：——

  日期：——