8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone
• 英文别名: 8-hydroxyquinoline-2-carboxaldehyde-(isonicotinyl)hydrazone；N'-[(E)-(8-hydroxyquinolin-2-yl)methylidene]pyridine-4-carbohydrazide；N-[(E)-(8-hydroxyquinolin-2-yl)methylideneamino]pyridine-4-carboxamide
• 化学式: C₁₆H₁₂N₄O₂
• 分子量: 292.297
• InChiKey: QQUJBYPCLIELSF-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异烟肼 、 8-羟基喹啉-2-甲醛 以 乙醇 、 水 为溶剂， 反应 8.0h， 以71%的产率得到8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone
  参考文献：
  名称：

  衍生自8-羟基喹啉-2-羧基醛和四种芳酰基肼的席夫碱配体的双核Ho（III）配合物的合成，晶体结构，抗氧化作用和DNA结合特性

  摘要：

  X射线晶体和其他结构分析表明，Ho（III）和每个新合成的配体均可通过在Ho（III）中心进行九配位而形成金属核配体化学计量比为1：1的双核Ho（III）配合物。 。每个配体均充当二元四齿配体，通过酚酸氧原子，喹啉基单元的氮原子和C N基团，– O–C N–基团（从O C–NH–基团被烯化和去质子化）与Ho（III）结合。）的芳酰肼侧链。一个DMF分子从一侧到金属离子与配体平面正交结合，而另一DMF和硝酸盐（双齿）从另一侧结合。该单体单元的二聚通过酚酸氧原子发生，从而导致中心平面四元（HoO）2戒指。DNA结合特性的研究表明，所有配体和Ho（III）配合物都可以通过插层结合小牛胸腺DNA，其结合常数为10 5 –10 6  M -1数量级，但是Ho（III）配合物表现出更强的结合力。对DNA的亲和力要高于配体。所有的配体和Ho（III）配合物都可以用作潜在的抗癌药物。抗氧化性能的研究表明，

  DOI：

  10.1016/j.jorganchem.2009.05.031

文献信息

• METHOD FOR PREPARING THE ANHYDROUS CRYSTALLINE FORM OF ISONIAZID-DERIVED HYDRAZONE, THUS PRODUCED CRISTALLINE POLYMORPH OF THE ANHYDROUS FORM, USE THEREOF FOR THE TREATMENT OF ALZHEIMER'S DISEASE, PARKINSONISM AND OTHER NEURODEGENERATIVE DISORDERS, AND PHARMACEUTICAL COMPOSITION
  申请人：Rey Nicolás Adrián

  公开号：US20170158665A1

  公开（公告）日：2017-06-08

  The present invention relates to the method for preparing the anhydrous crystalline form of isoniazid-derived hydrazone (8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone), to the thus produced polymorph and to the use thereof for the treatment of Alzheimer's disease and parkinsonism, inter alia, and to a pharmaceutical composition.

  本发明涉及制备异烟肼衍生物酰肼（8-羟基喹啉-2-甲醛异烟酰肼酰肼）无水晶形态的方法，以及由此产生的多晶形态和其用于治疗阿尔茨海默病和帕金森病等疾病的用途，还包括一种制药组合物。
• Method for preparing the anhydrous crystalline form of isoniazid-derived hydrazone, thus produced cristalline polymorph of the anhydrous form, use thereof for the treatment of Alzheimer's disease, parkinsonism and other neurodegenerative disorders, and pharmaceutical composition
  申请人：FACULDADES CATÓLICAS, Associação sem fins Lucrativos, Mantenedora da Pontificia Universidade

  公开号：US10189811B2

  公开（公告）日：2019-01-29

  The present invention relates to the method for preparing the anhydrous crystalline form of isoniazid-derived hydrazone (8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone), to the thus produced polymorph and to the use thereof for the treatment of Alzheimer's disease and parkinsonism, inter alia, and to a pharmaceutical composition.

  本发明涉及异烟肼衍生腙（8-羟基喹啉-2-甲醛异烟酰腙）的无水结晶形式的制备方法、由此产生的多晶体及其在治疗阿尔茨海默病和帕金森病等方面的用途，以及一种药物组合物。
• Method for preparing the anhydrous crystalline form of isoniazid-derived hydrazone, thus produced crystalline polymorph of the anyhydrous form, use thereof for the treatment of alzheimer's disease, parkinsonism and other neurodegenerative disorders, and pharamceutical composition
  申请人：FACULDADDES CATÓLICAS, Associação sem fins Lucrativos, Mantenedora da Pontificia Universidade Católica

  公开号：US10316019B2

  公开（公告）日：2019-06-11

  A method for preparing the anhydrous crystalline form of isoniazid-derived hydrazone (8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone), to the thus produced polymorph and to the use thereof for the treatment of Alzheimer's disease and parkinsonism, inter alia, and to a pharmaceutical composition.

  一种制备异烟肼衍生腙（8-羟基喹啉-2-甲醛异烟酰腙）无水结晶形式的方法，以及由此产生的多晶体和用于治疗阿尔茨海默病和帕金森病等疾病的药物组合物。
• Structural and vibrational study of 8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone – A potential metal–protein attenuating compound (MPAC) for the treatment of Alzheimer’s disease
  作者：Leonardo Viana de Freitas、Cecilia C.P. da Silva、Javier Ellena、Luiz Antônio Sodré Costa、Nicolás A. Rey

  DOI：10.1016/j.saa.2013.06.105

  日期：2013.12

  A comprehensive structural and vibrational study of the potential metal protein attenuating compound 8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone is reported. X-ray diffraction data, as well as FT-IR and Raman frequencies, were compared with the respective theoretical values obtained from DFT calculations. Theory agrees well with experiment. In this context, an attempt of total assignment concerning the FT-IR and Raman spectra of the title compound was performed, shedding new light on previous partial assignments published elsewhere. (C) 2013 Elsevier B.V. All rights reserved.
• METHOD FOR PREPARING THE ANHYDROUS CRYSTALLINE FORM OF ISONIAZID-DERIVED HYDRAZONE, THUS PRODUCED CRYSTALLINE POLYMORPH OF THE ANYHYDROUS FORM, USE THEREOF FOR THE TREATMENT OF ALZHEIMER'S DISEASE, PARKINSONISM AND OTHER NEURODEGENERATIVE DISORDERS, AND PHARAMCEUTICAL COMPOSITION
  申请人：FACULDADES CATÓLICAS, Associação sem fins Lucrativos, Mantenedora da Pontifícia Universidade

  公开号：US20190106408A1

  公开（公告）日：2019-04-11

  A method for preparing the anhydrous crystalline form of isoniazid-derived hydrazone (8-hydroxyquinoline-2-carboxaldehyde isonicotinoyl hydrazone), to the thus produced polymorph and to the use thereof for the treatment of Alzheimer's disease and parkinsonism, inter alia, and to a pharmaceutical composition.