3-chloro-N-(3-chlorobenzoyl)-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzamide | 1361327-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-chloro-N-(3-chlorobenzoyl)-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzamide
• 英文别名: 3-chloro-N-(3-chlorobenzoyl)-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide；2-bis(3-chlorobenzoyl)amino-3-chloro-1,4-naphthoquinone；IMDNQ 10；US9422231, Imdnq10；3-chloro-N-(3-chlorobenzoyl)-N-(3-chloro-1,4-dioxonaphthalen-2-yl)benzamide
• CAS: 1361327-63-0
• 化学式: C₂₄H₁₂Cl₃NO₄
• 分子量: 484.723
• InChiKey: SKFYRQOCVYGFLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-3-氯-1,4-萘醌 、 3-氯苯甲酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 以31%的产率得到3-chloro-N-(3-chlorobenzoyl)-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzamide
  参考文献：
  名称：

  Synthesis and Characterization of Novel Unsymmetrical and Symmetrical 3-Halo- or 3-Methoxy-substituted 2-Dibenzoylamino-1,4-naphthoquinone Derivatives

  摘要：

  对称和不对称的3-卤代或3-甲氧基取代的2-二苯甲酰氨基-1,4-纳弗喹啉类似物通过氢化钠促进的双酰化反应合成，平均产率为45%，反应底物为2-氨基-3-氯-1,4-纳弗喹啉、2-氨基-3-溴-1,4-纳弗喹啉和2-氨基-3-甲氧基-1,4-纳弗喹啉。

  DOI：

  10.3390/molecules18021973

文献信息

• Antitrypanosomal activities and cytotoxicity of some novel imidosubstituted 1,4-naphthoquinone derivatives
  作者：Mozna H. Khraiwesh、Clarence M. Lee、Yakini Brandy、Emmanuel S. Akinboye、Solomon Berhe、Genelle Gittens、Muneer M. Abbas、Franklin R. Ampy、Mohammad Ashraf、Oladapo Bakare

  DOI：10.1007/s12272-012-0103-1

  日期：2012.1

  The antitrypanosomal activities, cytotoxicity, and selectivity indices of eleven imido-substituted 1,4-naphthoquinone derivatives and nifurtimox have been studied. Compared to nifurtimox (IC50 = 10.67 μM), all the imido-naphthoquinone analogs (IMDNQ1-IMDNQ11) are more potent on Trypanosoma cruzi with IC50 values ranging from 0.7 μM to 6.1 μM (p < 0.05). Studies of the cytotoxic activities of these compounds on a Balb/C 3T3 mouse fibroblast cell line revealed that four of these compounds, IMDNQ1, IMDNQ2, IMDNQ3, and IMDNQ10 displayed selectivity indices of 60.25, 53.97, 31.83, and 275.3, respectively, rendering them significantly (p < 0.05) more selective in inhibiting the parasite growth than nifurtimox (selectivity index = 10.86).

  研究了十一种亚氨基取代的 1,4-萘醌衍生物和硝呋噻菌胺的抗锥虫活性、细胞毒性和选择性指数。与硝呋太保（IC50 = 10.67 μM）相比，所有亚氨基萘醌类似物（IMDNQ1-IMDNQ11）对克鲁斯锥虫的作用更强，IC50 值从 0.7 μM 到 6.1 μM（p < 0.05）。对这些化合物在 Balb/C 3T3 小鼠成纤维细胞系上的细胞毒性活性的研究表明，其中四种化合物 IMDNQ1、IMDNQ2、IMDNQ3 和 IMDNQ10 的选择性指数分别为 60.25、53.97、31.83 和 275.3，使它们在抑制寄生虫生长方面的选择性显著高于硝呋太保（选择性指数 = 10.86）（p < 0.05）。
• [EN] METHODS FOR TREATING LEISHMANIASIS<br/>[FR] MÉTHODES DE TRAITEMENT DE LA LEISHMANIOSE
  申请人：UNIV HOWARD

  公开号：WO2013074930A1

  公开（公告）日：2013-05-23

  Methods are provided to inhibit proliferation of Leishmania parasites, and in particular Leishmania donovani with imido-substituted 1,4-naphthoquinones, including novel compounds. Administering an imido-substituted 1,4-naphthoquinone can be used to provide prophylaxis or treatment to a patient in need of treatment against leishmaniasis disease.

  提供了一种方法来抑制利什曼原虫（Leishmania）的增殖，特别是对利什曼东非原虫（Leishmania donovani）使用带有亚胺取代的1,4-萘醌类化合物，包括新颖的化合物。给予亚胺取代的1,4-萘醌类化合物可以用于为需要治疗利什曼病的患者提供预防或治疗。
• METHODS FOR TREATING LEISHMANIASIS
  申请人：HOWARD UNIVERSITY

  公开号：US20140336187A1

  公开（公告）日：2014-11-13

  Methods are provided to inhibit proliferation of Leishmania parasites, and in particular Leshmania donovani with imido-substituted 1,4-naphthoquinones, including novel compounds. Administering an imido-substituted 1,4-naphthoquinone can used to provide prophylaxis or treatment to a patient in need of treatment against leishmaniasis disease.

  提供了抑制利什曼原虫增殖的方法，特别是使用含亚胺基取代的1,4-萘醌类化合物抑制利什曼原虫的增殖，包括新型化合物。给予亚胺基取代的1,4-萘醌类化合物可以用于为需要治疗利什曼病的患者提供预防或治疗。
• ASCORBIC ACID, QUINONE COMPOUND, AND SODIUM GLUCOSE COTRANSPORTER INHIBITOR FOR TREATING CANCER
  申请人：IC-Medtech Corp.

  公开号：EP3490543A1

  公开（公告）日：2019-06-05
• METHOD FOR INHIBITING TRYPANOSOMA CRUZI
  申请人：Bakare Oladapo

  公开号：US20150073177A1

  公开（公告）日：2015-03-12

  Methods are provided to inhibit proliferation of Trypanosoma cruzi with imido-substituted 1,4-naphthoquinones, including novel compounds. Administering an imido-substituted 1,4-naphthoquinone can be used to provide prophylaxis or treatment to a patient in need of treatment against Chagas disease.