3-benzamido-4-methoxybenzoic acid | 712286-76-5

• 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: 3-benzamido-4-methoxybenzoic acid
• 英文别名: 4-Methoxy-3-[(phenylcarbonyl)amino]benzoic acid
• CAS: 712286-76-5
• 化学式: C₁₅H₁₃NO₄
• mdl: MFCD04069083
• 分子量: 271.273
• InChiKey: IIMGAYPEVAILBO-UHFFFAOYSA-N

物化性质

• 沸点：
  377.5±32.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzamido-4-methoxybenzoic acid 、 氯甲酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Structure-Based Design and Synthesis of Novel Inhibitors Targeting HDAC8 from Schistosoma mansoni for the Treatment of Schistosomiasis

  摘要：

  Schistosomiasis is a major neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy consists of mass treatment with the only available drug, praziquantel. In this study, a series of new benzohydroxamates were prepared as potent inhibitors of Schistosoma mansoni histone deacetylase 8 (smHDAC8). Crystallographic analysis provided insights into the: inhibition mode of smHDAC8 activity by these 3-amidobenzohydroxamates. The newly designed inhibitors were evaluated in screens for enzyme inhibitory activity against schistosome and human HDACs. Twenty-seven compounds were found to be active in the nanomolar range, and some of them showed selectivity toward smHDAC8 over the major human HDACs (I and 6). The active benzohydroxamates were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Four of these showed significant dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.

  DOI：

  10.1021/acs.jmedchem.5b01478
• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-benzamido-4-methoxybenzoic acid
  参考文献：
  名称：

  Structure-Based Design and Synthesis of Novel Inhibitors Targeting HDAC8 from Schistosoma mansoni for the Treatment of Schistosomiasis

  摘要：

  Schistosomiasis is a major neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy consists of mass treatment with the only available drug, praziquantel. In this study, a series of new benzohydroxamates were prepared as potent inhibitors of Schistosoma mansoni histone deacetylase 8 (smHDAC8). Crystallographic analysis provided insights into the: inhibition mode of smHDAC8 activity by these 3-amidobenzohydroxamates. The newly designed inhibitors were evaluated in screens for enzyme inhibitory activity against schistosome and human HDACs. Twenty-seven compounds were found to be active in the nanomolar range, and some of them showed selectivity toward smHDAC8 over the major human HDACs (I and 6). The active benzohydroxamates were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Four of these showed significant dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.

  DOI：

  10.1021/acs.jmedchem.5b01478

文献信息

• Synthesis and antiviral activity of substituted bisaryl amide compounds as novel influenza virus inhibitors
  作者：Lan-hu Hao、Yan-ping Li、Wei-ying He、Hui-qiang Wang、Guang-zhi Shan、Jian-dong Jiang、Yu-huan Li、Zhuo-rong Li

  DOI：10.1016/j.ejmech.2012.07.008

  日期：2012.9

  pharmaceutical investigation. In this work, substituted bisaryl amide compounds were found to be a new class of potential anti-influenza agents, and a series of substituted bisaryl amide compounds were synthesised and evaluated for their anti-influenza virus activities. The analysis of the results produced a preliminary structure–activity relationship study (SAR). Compounds 1a, 1g, 1h, 1j, 1l and 1n exhibited

  每年，流感病毒都是致死和发病的持续原因，因此，它本身已成为药物研究的重要目标。在这项工作中，发现取代的双芳基酰胺化合物是一类潜在的抗流感药物，并且合成了一系列取代的双芳基酰胺化合物并评估了它们的抗流感病毒活性。结果分析产生了初步的结构-活性关系研究（SAR）。化合物1a，1g，1h，1j，1l和1n对甲型流感病毒（A /广东罗湖/ 219/2006，H1N1）表现出明显的抗病毒活性，抑制浓度为50％（IC50）用于病毒生长，范围从12.5到59.0μM。具体而言，化合物1j还具有抗耐奥司他韦的流感病毒（A / Jinnan / 15/2009）和B型流感病毒（B / Jifang / 13/97）的抗病毒活性，IC 50值分别为9.2μM和21.4μM。因此，化合物1j作为抗流感病毒的候选药物值得进一步研究。
• USE OF INHIBITORS OF SCAVENGER RECEPTOR CLASS PROTEINS FOR THE TREATMENT OF INFECTIOUS DISEASES
  申请人：HANNUS MICHAEL

  公开号：US20120276121A1

  公开（公告）日：2012-11-01

  The present invention relates to the use of inhibitors of scavenger receptor class proteins, in particular ScarB1 for the production of a medicament for treatment of and/or prophylaxis against infections, involving liver cells and/or hematopoietic cells, in particular malaria.
• Structure-Based Design and Synthesis of Novel Inhibitors Targeting HDAC8 from <i>Schistosoma mansoni</i> for the Treatment of Schistosomiasis
  作者：Tino Heimburg、Alokta Chakrabarti、Julien Lancelot、Martin Marek、Jelena Melesina、Alexander-Thomas Hauser、Tajith B. Shaik、Sylvie Duclaud、Dina Robaa、Frank Erdmann、Matthias Schmidt、Christophe Romier、Raymond J. Pierce、Manfred Jung、Wolfgang Sippl

  DOI：10.1021/acs.jmedchem.5b01478

  日期：2016.3.24

  Schistosomiasis is a major neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy consists of mass treatment with the only available drug, praziquantel. In this study, a series of new benzohydroxamates were prepared as potent inhibitors of Schistosoma mansoni histone deacetylase 8 (smHDAC8). Crystallographic analysis provided insights into the: inhibition mode of smHDAC8 activity by these 3-amidobenzohydroxamates. The newly designed inhibitors were evaluated in screens for enzyme inhibitory activity against schistosome and human HDACs. Twenty-seven compounds were found to be active in the nanomolar range, and some of them showed selectivity toward smHDAC8 over the major human HDACs (I and 6). The active benzohydroxamates were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Four of these showed significant dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.