N-(2'-methyl-5'-nitrophenyl)anthranilic acid | 21193-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2'-methyl-5'-nitrophenyl)anthranilic acid
• 英文别名: 2-(2-Methyl-5-nitroanilino)benzoic acid
• CAS: 21193-40-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: NCONXNGRLNDBDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2'-methyl-5'-nitrophenyl)anthranilic acid 在 硫酸 作用下， 生成 4-methyl-1-nitro-9-oxoacridan
  参考文献：
  名称：

  Clemo; Perkin; Robinson, Journal of the Chemical Society, 1924, vol. 125, p. 1780

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基碘酸 、 2-氨基-4-硝基甲苯 在 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到N-(2'-methyl-5'-nitrophenyl)anthranilic acid
  参考文献：
  名称：

  Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine

  摘要：

  The nitroacridine derivative 9-[[3-(dimethylamino)propyl]amino]-1-nitroacridine (nitracrine) is selectively cytotoxic to hypoxic tumor cells in culture. However, the compound undergoes reductive metabolism too rapidly, with the reduction not being sufficiently inhibited by molecular oxygen in aerobic tissues, for it to demonstrate the same activity in vivo. In a search for derivatives with lower reduction potentials, we have synthesized and evaluated a series of derivatives bearing 4-substituents with a wide range of electronic properties. The one-electron reduction potentials (E(1] of these compounds, when compared under conditions of equivalent ionization, were highly correlated with sigma p values. However, at pH 7 the influence of substituent electronic properties was modified by prototrophic equilibria, with the basic nature of the acridine limiting the extent to which ring substituent electronic effects can be used to modulate reduction potential of the 1-nitro group. Nevertheless, comparison of the kinetics of the killing of AA8 cells under hypoxia suggests that some metabolic stabilization of the compounds can be achieved by the use of electron-donating substituents, with such compounds retaining the hypoxia-selective toxicity of nitracrine in cell culture. However, the 4-substituted nitracrines show no clear relationship between E(1) and cytotoxic potency, in distinct contrast to simpler nitroheterocycles such as nitroimidazoles.

  DOI：

  10.1021/jm00121a006

文献信息

• Chloroacridine derivatives as potential anticancer agents which may act as tricarboxylic acid cycle enzyme inhibitors
  作者：Miroslawa Cichorek、Anna Ronowska、Krystyna Dzierzbicka、Monika Gensicka-Kowalewska、Milena Deptula、Iwona Pelikant-Malecka

  DOI：10.1016/j.biopha.2020.110515

  日期：2020.10

  structure changes (phosphatidylserine externalization), caspase activation, and ROS presence. The energetic state of cells was estimated based on NAD and ATP levels, and the activity of tricarboxylic acid cycle enzymes (pyruvate dehydrogenase complex, aconitase, isocitrate dehydrogenase). Results The chloroacridines affect biological forms of melanoma in different ways. Amelanotic (Ab) melanoma (with inhibited

  目的 本文涉及 9-氯-1-硝基吖啶 ( 1a ) 和 9-氯-4-甲基-1-硝基吖啶 ( 1b ) 对两种生物学上不同的黑色素瘤形式：黑色素瘤和无黑素瘤的细胞毒性。黑色素瘤是一种以高度异质性和对化学疗法的敏感性差为特征的肿瘤。在我们合成的新类似物中，化合物1b表现出最高的抗癌效力。因此，在本研究中，我们分析了 1a 及其 4-甲基化衍生物1b对两种生物黑色素瘤形式的作用机制，包括增殖、细胞死亡机制和能量状态。 方法 通过XTT测定评估细胞毒性。通过质膜结构变化（磷脂酰丝氨酸外化）、半胱天冬酶活化和 ROS 存在来估计细胞死亡。根据 NAD 和 ATP 水平以及三羧酸循环酶（丙酮酸脱氢酶复合物、乌头酸酶、异柠檬酸脱氢酶）的活性估计细胞的能量状态。 结果 氯吖啶以不同方式影响黑色素瘤的生物学形式。无黑色素 (Ab) 黑色素瘤（黑色素生成受抑制且恶性程度更高）对氯吖啶的作用特别敏感。Ab 黑色
• Carrasco, Ramon; Pellon, Rolando F.; Elguero, Jose, Synthetic Communications, 1989, vol. 19, # 11-12, p. 2077 - 2080
  作者：Carrasco, Ramon、Pellon, Rolando F.、Elguero, Jose、Goya, Pilar、Paez, Juan Antonio

  DOI：——

  日期：——
• Weiss; Katz, Monatshefte fur Chemie, 1928, vol. 50, p. 227
  作者：Weiss、Katz

  DOI：——

  日期：——
• CARRASCO, RAMON;PELLON, ROLANDO F.;ELGUERO, JOSE;GOYA, PILAR;ANTONIO, PAE+, SYNTH. COMMUN., 19,(1989) N1-12, C. 2077-2080
  作者：CARRASCO, RAMON、PELLON, ROLANDO F.、ELGUERO, JOSE、GOYA, PILAR、ANTONIO, PAE+

  DOI：——

  日期：——
• WYSOCKA-SKRZELA B.; LEDOCHOWSKI A., ROCZ. CHEM. <ROCH-AC>, 1976, 50, NO 1, 127-131
  作者：WYSOCKA-SKRZELA B.、 LEDOCHOWSKI A.

  DOI：——

  日期：——