2-hydroxy-N-(4-cyanophenyl)benzamide | 16308-11-5

• 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: 2-hydroxy-N-(4-cyanophenyl)benzamide
• 英文别名: N-(4-cyanophenyl)-2-hydroxybenzamide；2-(4-cyanophenylcarbamoyl)phenol；4-cyano-salicylanilide
• CAS: 16308-11-5
• 化学式: C₁₄H₁₀N₂O₂
• mdl: MFCD01428921
• 分子量: 238.246
• InChiKey: FUAUEJWQTUPNQR-UHFFFAOYSA-N

物化性质

• 沸点：
  361.9±27.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-(4-cyanophenyl)benzamide 在 硫酸 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Novel ZnII complexes of 2-(2-hydroxyphenyl)benzothiazoles ligands: electroluminescence and application as host materials for phosphorescent organic light-emitting diodes

  摘要：

  设计并合成了一组含有2-羟基苯基苯并噻唑（BTZ）配体的新型锌配合物，其中BTZ配体中苯并噻唑环的6位上连接有不同的取代基（OCH3、CH3、F、CF3、COOCH2CH3）。研究了这些锌配合物的光致发光（PL）和电致发光（EL）行为。通过简单地改变取代基，这些锌配合物的发射颜色很容易从蓝绿色调整为黄色，强吸电子取代基有利于较长波长的荧光。当这些锌络合物用作有机发光二极管（OLED）中的非掺杂发光层时，获得了高效的EL。此外，这些锌配合物被证明能够充当红色磷光OLED中铱磷光体的三重态主体。以本发明的锌配合物为主体、三(2-苯基异喹啉)铱作为掺杂发射极的红色磷光OLED实现了17.5%的高外量子效率，与采用本发明的锌配合物的器件的外量子效率(12.6%)相比大大提高。传统的4,4′-双(N-咔唑基)联苯(CBP)作为主体。本研究成功开发了新型锌配合物作为磷光 OLED 的电子传输主体材料。

  DOI：

  10.1039/c2jm34599d
• 作为产物：
  描述：

  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-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
• 作为试剂：
  描述：

  水杨酸苯酯 、 对氨基苯腈 在 2-hydroxy-N-(4-cyanophenyl)benzamide 、 S-1,1'-联-2-萘酚 作用下， 生成 2-hydroxy-N-(4-cyanophenyl)benzamide
  参考文献：
  名称：

  Process for preparing aldehyde compounds

  摘要：

  本发明涉及一种通过氢甲酰化反应，以及在催化剂系统的存在下，由一种不饱和化合物制备有机醛化合物的方法。所述催化剂系统包括一种第VIII族金属和一种双齿磷配体，其具有两个三价磷原子与水杨基苯胺基团结合。

  公开号：

  US06664427B1

文献信息

• Amidino derivatives and drugs containing the same as the active ingredient
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US06358960B1

  公开（公告）日：2002-03-19

  The novel amidino derivatives of the formula (I): wherein all the symbols are as in specification defined; have an inhibitory activity of a blood coagulation factor VIIa and are useful for treatment and/or prevention of several angiopathy caused by enhancing a coagulation activity, such as disseminated intravascular coagulation, coronary thrombosis, cerebral infarction, cerebral embolism, transient ischemic attack, cerebrovascular disorders, pulmonary vascular diseases, deep venous thrombosis, peripheral arterial obstruction, thrombosis after artificial vascular transplantation and artificial valve transplantation, post-operative thrombosis, reobstruction and restenosis after coronary artery bypass operation, reobstruction and restenosis after PTCA or PTCR, thrombosis by extracorporeal circulation and procoagulative diseases such as glomerlonephriitis.

  该式(I)的胍基衍生物小说：其中所有符号均如规范中所定义；具有抑制血凝血因子VIIa的活性，并可用于治疗和/或预防由增强凝血活性引起的多种血管病，如弥散性血管内凝血、冠状动脉血栓形成、脑梗死、脑栓塞、短暂性缺血发作、脑血管疾病、肺血管疾病、深静脉血栓形成、周围动脉阻塞、人工血管移植后血栓形成和人工瓣膜移植后血栓形成、术后血栓形成、冠状动脉旁路手术后再阻塞和再狭窄、PTCA或PTCR后再阻塞和再狭窄、体外循环引起的血栓形成以及像肾小球肾炎这样的促凝病。
• 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。
• Multivariate Regression with Substituent Shift Increments. IV. 2-(4-X-Phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-Phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
  作者：Miroslav Holík、Zdeněk Friedl、Karel Waisser、Jiří Gregor

  DOI：10.1135/cccc19991709

  日期：——

  Two series of para disubstituted benzenes were studied: 2-(4-X-phenyl)-1,3-dihydro- 2H-isoindole-1,3-diones (1) and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones (2). Their ¹H and ¹³C chemical shifts were correlated with substituent shift increments (SSI) a_j and z_j, respectively. For ¹³C chemical shifts, all four z_j values, z_i, z_o, z_m, and z_p, were used to check the assignment and to find out possible variables for improvement of regression equations. Significant deviations from plain additivity were observed in the case of δ_H3 and δ_C3 chemical shifts. This can be explained by changes in diamagnetic anisotropy contribution induced by different twist of 4-substituent from the benzene plane caused by variable substituent in position 1.

  研究了两组para二取代苯：2-(4-X-苯基)-1,3-二氢-2H-异吲哚-1,3-二酮(1)和3-(4-X-苯基)-3,4-二氢-2H-1,3-苯并噁嗪-2,4-二酮(2)。它们的¹H和¹³C化学位移与取代基位移增量(SSl) a_j和z_j相关。对于¹³C化学位移，所有四个z_j值，z_i，z_o，z_m和z_p，都被用来检查分配并找出可能改进回归方程的变量。在δ_H3和δ_C3化学位移的情况下观察到明显的偏离简单加性。这可以通过由位于位置1的可变取代基引起的苯环平面外4-取代基的不同扭曲引起的抗磁性异向贡献的变化来解释。
• [EN] INHIBITORS OF CREB-CBP INTERACTION FOR TREATMENT OF LEUKEMIA<br/>[FR] INHIBITEURS DE L'INTERACTION CREB-CBP POUR LE TRAITEMENT DE LA LEUCÉMIE
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2017156489A1

  公开（公告）日：2017-09-14

  Compounds and methods are provided for inhibiting a CREB-CBP protein-protein interaction in a sample. In some cases, the method includes modulating transcription of CREB in a cell that overexpresses CREB. Also provided are methods of inhibiting the proliferation of a cancer cell. The subject CREB transcription inhibitor compounds include a substituted salicylamide or a prodrug thereof. Methods of alleviating symptoms associated with cancer (e.g., Acute Myeloid Leukemia (AML) or Acute Lymphomblastic Leukemia (ALL)) in a subject in need thereof are also provided. Pharmaceutical compositions including the subject compounds find use in treating cancer. The subject compounds may be formulated or provided to a subject in combination with a second agent, e.g. an anticancer agent.

  提供了一种抑制样本中CREB-CBP蛋白质相互作用的化合物和方法。在某些情况下，该方法包括调节过表达CREB的细胞中CREB的转录。还提供了抑制癌细胞增殖的方法。所述CREB转录抑制剂化合物包括替代水杨酰胺或其前药。还提供了一种缓解与癌症相关症状（例如急性髓细胞白血病（AML）或急性淋巴细胞白血病（ALL））的方法，适用于需要该方法的受试者。包括所述化合物的药物组合物用于治疗癌症。所述化合物可以与第二药剂（例如抗癌药剂）组合配制或提供给受试者。
• AMIDINO DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1078917A1

  公开（公告）日：2001-02-28

  The novel amidino derivatives of the formula (I): wherein all the symbols are as in specification defined; have an inhibitory activity of a blood coagulation factor VIIa and are useful for treatment and / or prevention of several angiopathy caused by enhancing a coagulation activity, such as disseminated intravascular coagulation, coronary thrombosis, cerebral infarction, cerebral embolism, transient ischemic attack, cerebrovascular disorders, pulmonary vascular diseases, deep venous thrombosis, peripheral arterial obstruction, thrombosis after artificial vascular transplantation and artificial valve transplantation, post-operative thrombosis, reobstruction and restenosis after coronary artery bypass operation, reobstruction and restenosis after PTCA or PTCR, thrombosis by extracorporeal circulation and procoagulative diseases such as glomerlonephriitis.

  式 (I) 的新型脒基衍生物： 其中所有符号与说明书中的定义相同； 具有抑制凝血因子 VIIa 的活性，可用于治疗和/或预防因增强凝血活性而引起的多种血管病变，如弥散性血管内凝血、冠状动脉血栓形成、脑梗塞、脑栓塞、短暂性脑缺血发作、脑血管疾病、肺血管疾病、深静脉血栓形成、外周动脉阻塞、人工血管移植后的血栓形成、深静脉血栓形成、外周动脉阻塞、人工血管移植和人工瓣膜移植术后血栓形成、术后血栓形成、冠状动脉搭桥术后再梗阻和再狭窄、PTCA 或 PTCR 术后再梗阻和再狭窄、体外循环血栓形成以及肾小球肾炎等促凝血疾病。