N-phenyl-6-chloro-3-nitrobenzoic acid | 55776-07-3

• 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-phenyl-6-chloro-3-nitrobenzoic acid
• 英文别名: 2-anilino-6-chloro-3-nitrobenzoic acid；6-chloro-3-nitro-2-(phenylamino)benzoic acid；2-Anilino-6-chlor-3-nitro-benzoesaeure
• CAS: 55776-07-3
• 化学式: C₁₃H₉ClN₂O₄
• 分子量: 292.678
• InChiKey: YPYGSSGBUWKFOG-UHFFFAOYSA-N

物化性质

• 熔点：
  206 °C
• 沸点：
  428.4±45.0 °C(Predicted)
• 密度：
  1.525±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-phenyl-6-chloro-3-nitrobenzoic acid 在 potassium carbonate 、 硝基苯 、 三氯氧磷 作用下， 生成 1-(4-nitro-9-oxo-9,10-dihydro-acridin-1-ylamino)-anthraquinone
  参考文献：
  名称：

  Studies on Mexican Cactaceae. II. Opuntia megarrhiza, a poorly known endemic from San Luis Potosí, Mexico

  摘要：

  Opuntia megarrhiza Rose (Cactaceae) is a species endemic to central San Luis Potosi,, Mexico that, since originally described in 1906, has remained poorly understood. A comprehensive morphological description is presented and its presumed taxonomic affinity with O. chaffeyi is discussed. General accounts of its distribution, ecology, uses, and conservation status are presented.

  DOI：

  10.1007/bf02809653
• 作为产物：
  描述：

  2,6-二氯苯甲酸 在 硫酸 、 硝酸 作用下， 生成 N-phenyl-6-chloro-3-nitrobenzoic acid
  参考文献：
  名称：

  Studies on Mexican Cactaceae. II. Opuntia megarrhiza, a poorly known endemic from San Luis Potosí, Mexico

  摘要：

  Opuntia megarrhiza Rose (Cactaceae) is a species endemic to central San Luis Potosi,, Mexico that, since originally described in 1906, has remained poorly understood. A comprehensive morphological description is presented and its presumed taxonomic affinity with O. chaffeyi is discussed. General accounts of its distribution, ecology, uses, and conservation status are presented.

  DOI：

  10.1007/bf02809653

文献信息

• Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides
  作者：Gordon W. Rewcastle、William A. Denny、Bruce C. Baguley

  DOI：10.1021/jm00388a017

  日期：1987.5

  antitumor drugs, a series of substituted N-[2-(dimethylamino)ethyl]phenazine-1-carboxamides have been synthesized and evaluated. Fluorine-directed ring closure of N-phenyl-3-nitroanthranilic acids provided a new, unequivocal synthesis of several of the required phenazine-1-carboxylic acids, and the corresponding carboxamides were prepared and evaluated against L1210 leukemia in vitro and against P388

  在对缺乏电子的DNA插入配体作为抗肿瘤药物的进一步研究中，合成并评估了一系列取代的N- [2-（二甲基氨基）乙基]吩嗪-1-羧酰胺。N-苯基-3-硝基邻氨基苯甲酸的氟定向闭环提供了几种必需的吩嗪-1-羧酸的新的，明确的合成，并制备了相应的羧酰胺，并针对体外L1210白血病和P388白血病进行了评估。刘易斯体内肺癌。吩嗪环上的取代被广泛耐受，并且所得化合物的细胞毒性与取代基的吸电子能力正相关。取代基的位置效应甚至更加明显，其中9-取代的化合物最为活跃。一阶导数
• Novel Inhibitors of NRH:Quinone Oxidoreductase 2 (NQO2): Crystal Structures, Biochemical Activity, and Intracellular Effects of Imidazoacridin-6-ones
  作者：Mark S. Dunstan、John Barnes、Matthew Humphries、Roger C. Whitehead、Richard A. Bryce、David Leys、Ian J. Stratford、Karen A. Nolan

  DOI：10.1021/jm200416e

  日期：2011.10.13

  the enzyme NQO2. By use of computational molecular modeling, a reliable QSAR was established, relating inhibitory potency with calculated binding affinity. Further, crystal structures of NQO2 containing two of the imidazoacridin-6-ones have been solved. To generate compounds with reduced off-target (DNA binding) effects, an N-oxide moiety was introduced into the tertiary aminoalkyl side chain of the

  Imidazoacridin-6-ones 被证明是 NQO2 酶的有效纳摩尔抑制剂。通过使用计算分子模型，建立了可靠的 QSAR，将抑制效力与计算的结合亲和力相关联。此外，已经解决了含有两种 imidazoacridin-6-ones 的 NQO2 的晶体结构。为了生成具有降低的脱靶（DNA 结合）效应的化合物，将N-氧化物部分引入到 imidazoacridin-6-ones 的叔氨基烷基侧链中。这导致一组八种癌细胞系的毒性大大降低，蛋白质结合减少，DNA结合和核积累减少。最后，N个β-氧化物显示出抑制细胞中 NQO2 酶功能的有效能力，因此，它可以作为药理学探针来研究体外和体内酶的特性。
• Triazoloacridin-6-ones as novel inhibitors of the quinone oxidoreductases NQO1 and NQO2
  作者：Karen A. Nolan、Matthew P. Humphries、John Barnes、Jeremy R. Doncaster、Mary C. Caraher、Nicola Tirelli、Richard A. Bryce、Roger C. Whitehead、Ian J. Stratford

  DOI：10.1016/j.bmc.2009.11.059

  日期：2010.1

  A range of triazoloacridin-6-ones functionalized at C5 and C8 have been synthesized and evaluated for ability to inhibit NQO1 and NQO2. The compounds were computationally docked into the active site of NQO1 and NQO2, and calculated binding affinities were compared with IC50 values for enzyme inhibition. Excellent correlation coefficients were demonstrated suggesting a predictive QSAR model for this series of structurally similar analogues. From this we have identified some of these triazoloacridin-6-ones to be the most potent NQO2 inhibitors so far reported. (C) 2009 Elsevier Ltd. All rights reserved.
• Romanowski, Jacek; Eckstein, Zygmunt, Polish Journal of Chemistry, 1984, vol. 58, # 1-3, p. 263 - 268
  作者：Romanowski, Jacek、Eckstein, Zygmunt

  DOI：——

  日期：——
• Capps David B., Dundar James, Kesten Suzanne R., Shillis Joan, Werbel Les+, J. Med. Chem., 35 (1992) N 26, S 4770-4778
  作者：Capps David B., Dundar James, Kesten Suzanne R., Shillis Joan, Werbel Les+

  DOI：——

  日期：——