4-Hydroxybenzoic acid (1-naphthylmethylene)hydrazide | 368453-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Hydroxybenzoic acid (1-naphthylmethylene)hydrazide
• 英文别名: 4-hydroxy-N'-[(E)-naphthalen-1-ylmethylidene]benzohydrazide；4-hydroxy-N-[(E)-naphthalen-1-ylmethylideneamino]benzamide
• CAS: 368453-98-9
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: HRXYFFSBWOIYMU-XDHOZWIPSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Hydroxybenzoic acid (1-naphthylmethylene)hydrazide 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以48%的产率得到4-Hydroxy-benzoic acid N''-naphthalen-1-ylmethyl-hydrazide
  参考文献：
  名称：

  Identification of Alkylidene Hydrazides as Glucagon Receptor Antagonists

  摘要：

  High throughput screening of our small molecule combinatorial library identified a class of benzoylnaphthalenehydrazones with modest affinity for the human glucagon receptor. Optimization of this initial hit through a series of targeted libraries and traditional medicinal chemistry led to ligands with nanomolar affinities. Pharmacological evaluation demonstrated that these ligands were competitive glucagon receptor antagonists. Intravenous administration of a representative benzoylnaphthalenehydrazone into rats attenuated glucagon-stimulated glucose levels.

  DOI：

  10.1021/jm000547o
• 作为产物：
  描述：

  1-萘甲醛 、 4-羟基苯甲酰肼 以69%的产率得到4-Hydroxybenzoic acid (1-naphthylmethylene)hydrazide
  参考文献：
  名称：

  Identification of Alkylidene Hydrazides as Glucagon Receptor Antagonists

  摘要：

  High throughput screening of our small molecule combinatorial library identified a class of benzoylnaphthalenehydrazones with modest affinity for the human glucagon receptor. Optimization of this initial hit through a series of targeted libraries and traditional medicinal chemistry led to ligands with nanomolar affinities. Pharmacological evaluation demonstrated that these ligands were competitive glucagon receptor antagonists. Intravenous administration of a representative benzoylnaphthalenehydrazone into rats attenuated glucagon-stimulated glucose levels.

  DOI：

  10.1021/jm000547o

文献信息

• Glucagon antagonists/inverse agonists
  申请人：Novo Nordisk A/S

  公开号：US06613942B1

  公开（公告）日：2003-09-02

  Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof are disclosed. The compounds act to antagonize the action of the glucagon peptide hormone.

  本发明公开了包含中央腙基结构的非肽化合物及其合成方法。这些化合物具有拮抗胰高血糖素肽激素作用的作用。
• [EN] GLUCAGON ANTAGONISTS/INVERSE AGONISTS<br/>[FR] ANTAGONISTES/AGONISTES INVERSES DU GLUCAGON
  申请人：NOVO NORDISK AS

  公开号：WO1999001423A1

  公开（公告）日：1999-01-14

  Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof. The compounds act to antagonize the action of the glucagon peptide hormone.

  非肽化合物包含一个中心肼基结构，并且其合成方法。这些化合物作用是拮抗胰高血糖素肽激素的作用。
• Identification of Alkylidene Hydrazides as Glucagon Receptor Antagonists
  作者：Anthony Ling、Yufeng Hong、Javier Gonzalez、Vlad Gregor、Alex Polinsky、Atsuo Kuki、Shenghua Shi、Kimberly Teston、Douglas Murphy、John Porter、Dan Kiel、James Lakis、Kenna Anderes、John May、Lotte Bjerre Knudsen、Jesper Lau

  DOI：10.1021/jm000547o

  日期：2001.9.1

  High throughput screening of our small molecule combinatorial library identified a class of benzoylnaphthalenehydrazones with modest affinity for the human glucagon receptor. Optimization of this initial hit through a series of targeted libraries and traditional medicinal chemistry led to ligands with nanomolar affinities. Pharmacological evaluation demonstrated that these ligands were competitive glucagon receptor antagonists. Intravenous administration of a representative benzoylnaphthalenehydrazone into rats attenuated glucagon-stimulated glucose levels.