2-[2-(phenylacetylamino)benzoylamino]benzoic acid | 457908-00-8

• 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: 2-[2-(phenylacetylamino)benzoylamino]benzoic acid
• 英文别名: N-(N-phenylacetyl-anthraniloyl)-anthranilic acid；N-(N-Phenylacetyl-anthraniloyl)-anthranilsaeure；Phenacetyl-anthranoyl-anthranilsaeure；2-[[2-[(2-phenylacetyl)amino]benzoyl]amino]benzoic acid
• CAS: 457908-00-8
• 化学式: C₂₂H₁₈N₂O₄
• 分子量: 374.396
• InChiKey: NMKNKSDCPFAGPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(phenylacetylamino)benzoylamino]benzoic acid 在 乙酸酐 作用下， 反应 0.25h， 以93%的产率得到6-benzyl-13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione
  参考文献：
  名称：

  An efficient, convenient synthesis of novel medium-sized 13 H -dibenzo[ d , h ][1,3,7]oxadiazecine-8,14-dione macrolides as anticipated antineoplastic agents

  摘要：

  A series of novel medium-sized 13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione macrolides (18-27, 30, 32) were synthesized in an ongoing effort to develop new antineoplastic agents. The synthon 2-(2-aminobenzoylamino)-benzoic acid. (7), for preparation of the target compounds, was prepared via the reaction of isatoic anhydride 5 and anthranilic acid 6. Nine compounds (18-20 24-27, 30. 32) were subjected to National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay. Among the compounds tested 6-benzyl-13H-dibenzo[d,h][1,3,7]oxadiazecine-8, 14-dione (26, NSC 721327), bearing the benzyl group at position 6, showed cytotoxic activity and subpanel selectivity against leukemia (CCRF-CEM), colon (HCC-2998), CNS (SNB-75) and melanoma (UACC-257) panels at log(10) GI(50) (M), compound concentration that inhibits 50% of cell growth, ranging from -4.08 to -4,59. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00047-0
• 作为产物：
  描述：

  靛红酸酐 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 2-[2-(phenylacetylamino)benzoylamino]benzoic acid
  参考文献：
  名称：

  An efficient, convenient synthesis of novel medium-sized 13 H -dibenzo[ d , h ][1,3,7]oxadiazecine-8,14-dione macrolides as anticipated antineoplastic agents

  摘要：

  A series of novel medium-sized 13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione macrolides (18-27, 30, 32) were synthesized in an ongoing effort to develop new antineoplastic agents. The synthon 2-(2-aminobenzoylamino)-benzoic acid. (7), for preparation of the target compounds, was prepared via the reaction of isatoic anhydride 5 and anthranilic acid 6. Nine compounds (18-20 24-27, 30. 32) were subjected to National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay. Among the compounds tested 6-benzyl-13H-dibenzo[d,h][1,3,7]oxadiazecine-8, 14-dione (26, NSC 721327), bearing the benzyl group at position 6, showed cytotoxic activity and subpanel selectivity against leukemia (CCRF-CEM), colon (HCC-2998), CNS (SNB-75) and melanoma (UACC-257) panels at log(10) GI(50) (M), compound concentration that inhibits 50% of cell growth, ranging from -4.08 to -4,59. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00047-0

文献信息

• ANTIVIRAL COMPOUNDS
  申请人：Wadell Göran

  公开号：US20130210915A1

  公开（公告）日：2013-08-15

  The present invention provides new antiviral compounds and pharmacological compositions comprising these new compounds and their use in the prophylaxis, prevention and treatment of viral infections, particularly adenovirus and herpes virus infections.

  本发明提供了新的抗病毒化合物和包括这些新化合物的药理组合物，以及它们在预防、预防和治疗病毒感染中的应用，特别是腺病毒和疱疹病毒感染。
• Synthesis, Biological Evaluation, and Structure–Activity Relationships of 2-[2-(Benzoylamino)benzoylamino]benzoic Acid Analogues as Inhibitors of Adenovirus Replication
  作者：Christopher T. Öberg、Mårten Strand、Emma K. Andersson、Karin Edlund、Nam Phuong Nguyen Tran、Ya-Fang Mei、Göran Wadell、Mikael Elofsson

  DOI：10.1021/jm201636v

  日期：2012.4.12

  2-[2-Benzoylamino)benzoylamino]benzoic acid (1) was previously identified as a potent and nontoxic antiadenoviral compound ( Antimicrob. Agents Chemother. 2010, 54, 3871). Here, the potency of 1 was improved over three generations of compounds. We found that the ortho, ortho substituent pattern and the presence of the carboxylic acid of 1 are favorable for this class of compounds and that the direction

  2-〔2-苯甲酰氨基）苯甲酰基氨基]苯甲酸（1）以前鉴定为一种有效的和无毒antiadenoviral化合物（Antimicrob。代理Chemother。 2010，54，3871）。在这里，1的效力在三代化合物中得到了提高。我们发现，邻位，邻位取代基模式和1的羧酸的存在对于此类化合物都是有利的，并且酰胺键的方向（如1所示）是必不可少的。N的一些可变性-末端部分是可耐受的，但是苯甲酰胺似乎是优选的。中间和C端环上的取代基发生变化，产生了两种有效的抑制剂35g和35j，EC 50 = 0.6μM，细胞毒性低。
• [EN] NEW ANTIVIRAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIVIRAUX
  申请人：WADELL GOERAN

  公开号：WO2011155898A1

  公开（公告）日：2011-12-15

  The present invention provides new antiviral compounds and pharmacological compositions comprising these new compounds and their use in the prophylaxis, prevention and treatment of viral infections, particularly adenovirus and herpes virus infections.

  本发明提供了新的抗病毒化合物和包含这些新化合物的药物组合物，以及它们在预防、防治病毒感染，特别是腺病毒和疱疹病毒感染中的应用。
• Methods for treating diseases related to the wnt pathway
  申请人：Sandia Corporation

  公开号：US10624949B1

  公开（公告）日：2020-04-21

  The present invention relates to methods for treating a disease, in which the disease arises from dysregulation of the Wnt signaling pathway. In some instances, the disease can be treated by administering a Wnt pathway inhibitory compound. In other instances, the method optionally includes conducting a genome-wide screening to determine one or more genes resulting in a reduced disease state and then identifying the gene(s) as being involved in the Wnt signaling pathway.

  本发明涉及治疗疾病的方法，其中疾病是由 Wnt 信号通路失调引起的。在某些情况下，可以通过施用抑制 Wnt 通路的化合物来治疗疾病。在其他情况下，该方法可选地包括进行全基因组筛选，以确定导致疾病状态降低的一个或多个基因，然后确定这些基因参与Wnt信号通路。
• Niementowski, Chemisches Zentralblatt, 1902, vol. 73, # II, p. 122
  作者：Niementowski

  DOI：——

  日期：——