N-(4-cyanophenyl)-3-hydroxy-2-naphthamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-cyanophenyl)-3-hydroxy-2-naphthamide
• 英文别名: N-(4-Cyanophenyl)-3-hydroxynaphthalene-2-carboxamide
• 化学式: C₁₈H₁₂N₂O₂
• 分子量: 288.305
• InChiKey: DRBIYQSSEMTUJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  N-(4-cyanophenyl)-3-hydroxy-2-naphthamide 在 五氯化磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 [3-[(4-cyanophenyl)carbamoyl]naphthalen-2-yl] dihydrogen phosphate
  参考文献：
  名称：

  Fluorescent Substrates for Potential Use in Enzyme-Linked Immunosorbent Assay of Membrane-Bound Nucleic Acids

  摘要：

  A number of phosphorylated fluorochromes were synthesized and tested for the alkaline phosphatase-linked fluorescence assay of membrane-bound nucleic acids. 3-Hydroxy-N-2'-biphenyl-2-naphthalenecarboxamide phosphate ester (HBNP) was found to be the most suitable for the assay. Nonfluorescent HBNP is hydrolyzed by phospholipase bound to the probe DNA to the highly fluorescent 3-hydroxy-N,2'-biphenyl-2-naphthalenecarboxamide (HBN). HBN is insoluble enough in aqueous medium to precipitate on the nylon membrane. Spots containing as little as 5 fg of lambda DNA can be successfully detected on the membrane with HBNP.

  DOI：

  10.1021/ac00080a022
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 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 N-(4-cyanophenyl)-3-hydroxy-2-naphthamide
  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

• [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。
• Naphthalene carboxamides as inhibitors of human cytomegalovirus DNA polymerase
  作者：Valerie A Vaillancourt、Michele M Cudahy、Sandra A Staley、Roger J Brideau、Steven J Conrad、Mary L Knechtel、Nancee L Oien、Janet L Wieber、Yoshihiko Yagi、Michael W Wathen

  DOI：10.1016/s0960-894x(00)00402-9

  日期：2000.9

  ortho-Hydroxynaphthalene carboxamides have been identified as inhibitors of HCMV DNA polymerase. SAR investigations have demonstrated that both the amide and hydroxy functionalities are required for activity. Substitution on the naphthalene ring has led to inhibitors with submicromolar IC(50)s against HCMV polymerase. These compounds have been found to be >100-fold selective for inhibition of HCMV polymerase versus human alpha polymerase and display antiviral activity in a cell-based plaque reduction assay. (C) 2000 Elsevier Science Ltd. All rights reserved.
• INHIBITORS OF CREB-CBP INTERACTION FOR TREATMENT OF LEUKEMIA
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：EP3426632A1

  公开（公告）日：2019-01-16
• US4999269A
  申请人：——

  公开号：US4999269A

  公开（公告）日：1991-03-12
• US5041349A
  申请人：——

  公开号：US5041349A

  公开（公告）日：1991-08-20