2-hydroxy-4-methoxy-N-(4-cyanophenyl)benzamide

• 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-hydroxy-4-methoxy-N-(4-cyanophenyl)benzamide
• 英文别名: N-(4-cyanophenyl)-2-hydroxy-4-methoxybenzamide；N-(4-cyanophenyl)-2-hydroxy-4-methoxy-benzamide
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: YDOBFTYIPAWRTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-methoxy-N-(4-cyanophenyl)benzamide 在 盐酸 、 氨 作用下， 以 乙醇 为溶剂， 反应 120.0h， 以51%的产率得到2-hydroxy-4-methoxy-N-(4-amidinophenyl)benzamide hydrochloride
  参考文献：
  名称：

  被设计为有望的抗氧化剂的新型甲氧基和羟基取代的杂芳族酰胺的生物潜力：合成，3D-QSAR分析和生物活性。

  摘要：

  本文讨论了25种新颖的mid基取代的苯甲酰胺的抗氧化和生物活性，这些苯甲酰胺具有连接到苯甲酰胺部分的各种杂芳族原子核，并且具有可变数量的甲氧基或羟基取代基。在Pinner反应中，从氰基前体获得带有bearing基或2-咪唑啉基取代基的目标化合物。生成了3D-QSAR模型，以预测25种新型芳香族和杂芳香族苯甲酰胺衍生物的抗氧化活性。使用体外分光光度法测试化合物的抗氧化活性。通过比较实验和计算预测的抗氧化活性，对3D-QSAR方法预测新型苯甲酰胺衍生物的活性进行了直接验证。发现所有新化合物的实验确定活性均在模型误差的标准偏差内。此后，讨论了合成化合物之间的构效关系。此外，测试了体外对HeLa细胞的抗增殖活性以及抗菌和抗真菌活性，以证实所制备化合物的其他生物活性。

  DOI：

  10.1021/acs.chemrestox.9b00256
• 作为产物：
  描述：

  4-甲氧基水杨酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-hydroxy-4-methoxy-N-(4-cyanophenyl)benzamide
  参考文献：
  名称：

  SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway

  摘要：

  Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.

  DOI：

  10.1016/j.bmcl.2019.06.023

文献信息

• Relationship between the Structure and Antimycobacterial Activity of Substituted Salicylanilides
  作者：Karel Waisser、Otakar Bureš、Pavel Holý、Jiří Kuneš、Radek Oswald、Lucie Jirásková、Milan Pour、Věra Klimešová、Lenka Kubicová、Jarmila Kaustová

  DOI：10.1002/ardp.200390004

  日期：2003.3

  A series of 143 salicylanilides substituted in positions 4 and 5 and in positions 3′ and 4′ was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii, and Mycobacterium avium. To describe the structure‐antimycobacterial activity relationships (QSARs), an approach based on the combination of the Free‐Wilson and Hansch

  合成了一系列在 4 和 5 位以及在 3' 和 4' 位被取代的 143 个水杨酰苯胺。评估了化合物对结核分枝杆菌、堪萨斯分枝杆菌和鸟分枝杆菌的体外抗分枝杆菌活性。为了描述结构-抗分枝杆菌活性关系（QSAR），采用了一种基于 Free-Wilson 和 Hansch 方法组合的方法（在苯环上的取代基的情况下使用取代基常数；指示参数用于酰基部分上的取代基）。还探讨了所有替代品的抗分枝杆菌活性与理化参数之间的关系。亲脂性参数的二次表示没有导致显着的相关性。
• Waisser, Karel; Bures; Holy, Pharmazie, 2003, vol. 58, # 2, p. 83 - 94
  作者：Waisser, Karel、Bures、Holy、Kunes、Oswald、Jiraskova、Pour、Klimesova、Palat Jr.、Kaustova、Danse、Moellmann

  DOI：——

  日期：——
• SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway
  作者：Hee-Don Chae、Nick Cox、Samanta Capolicchio、Jae Wook Lee、Naoki Horikoshi、Sharon Kam、Andrew A. Ng、Jeffrey Edwards、Tae-León Butler、Justin Chan、Yvonne Lee、Garrett Potter、Mark C. Capece、Corey W. Liu、Soichi Wakatsuki、Mark Smith、Kathleen M. Sakamoto

  DOI：10.1016/j.bmcl.2019.06.023

  日期：2019.8

  Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.
• Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity
  作者：Irena Sović、Maja Cindrić、Nataša Perin、Ida Boček、Irena Novaković、Ana Damjanović、Tatjana Stanojković、Mario Zlatović、Marijana Hranjec、Branimir Bertoša

  DOI：10.1021/acs.chemrestox.9b00256

  日期：2019.9.16

  biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the

  本文讨论了25种新颖的mid基取代的苯甲酰胺的抗氧化和生物活性，这些苯甲酰胺具有连接到苯甲酰胺部分的各种杂芳族原子核，并且具有可变数量的甲氧基或羟基取代基。在Pinner反应中，从氰基前体获得带有bearing基或2-咪唑啉基取代基的目标化合物。生成了3D-QSAR模型，以预测25种新型芳香族和杂芳香族苯甲酰胺衍生物的抗氧化活性。使用体外分光光度法测试化合物的抗氧化活性。通过比较实验和计算预测的抗氧化活性，对3D-QSAR方法预测新型苯甲酰胺衍生物的活性进行了直接验证。发现所有新化合物的实验确定活性均在模型误差的标准偏差内。此后，讨论了合成化合物之间的构效关系。此外，测试了体外对HeLa细胞的抗增殖活性以及抗菌和抗真菌活性，以证实所制备化合物的其他生物活性。