3,5-dihydroxy-2-pyridinecarbonitrile | 1378502-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,5-dihydroxy-2-pyridinecarbonitrile
• 英文别名: 3,5-Dihydroxypicolinonitrile；3,5-dihydroxypyridine-2-carbonitrile
• CAS: 1378502-14-7
• 化学式: C₆H₄N₂O₂
• 分子量: 136.11
• InChiKey: QCGOHJWKAKKRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dihydroxy-2-pyridinecarbonitrile 在 碳酸氢钠 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 116.0h， 生成 ethyl (S)-4,5-Dihydro-2-[3-hydroxy-5-(3,6-dioxaheptyloxy)-2-pyridinyl]-4-methyl-4-thiazolecarboxylate
  参考文献：
  名称：

  [EN] DESFERRITHIOCIN ANALOGS AND USES THEREOF
  [FR] ANALOGUES DE LA DESFERRITHIOCINE ET LEURS UTILISATIONS

  摘要：

  铁过载与病理条件相关，如氧化应激、输血性铁过载、地中海贫血、原发性血色病、继发性血色病、糖尿病、肝病、心脏病、癌症、放射损伤、神经或神经退行性疾病、弗里德雷希共济失调（FRDA）、黄斑变性、闭合性头部损伤、肠易激综合征和再灌注损伤。本发明提供使用式（A）和（J）的去铁胱醇类似物的方法和药物组合物，用于治疗和/或预防这些病理条件、金属（如铁、铝、镧系元素或锕系元素（如铀））过载症状和传染病（如疟疾）。

  公开号：

  WO2015077655A1
• 作为产物：
  描述：

  3,5-bis(4-methoxybenzyloxy)pyridine-2-carbonitrile 在 五甲基苯 、 三氟乙酸 作用下， 反应 22.0h， 以100%的产率得到3,5-dihydroxy-2-pyridinecarbonitrile
  参考文献：
  名称：

  [EN] DESFERRITHIOCIN ANALOGS AND USES THEREOF
  [FR] ANALOGUES DE LA DESFERRITHIOCINE ET LEURS UTILISATIONS

  摘要：

  铁过载与病理条件相关，如氧化应激、输血性铁过载、地中海贫血、原发性血色病、继发性血色病、糖尿病、肝病、心脏病、癌症、放射损伤、神经或神经退行性疾病、弗里德雷希共济失调（FRDA）、黄斑变性、闭合性头部损伤、肠易激综合征和再灌注损伤。本发明提供使用式（A）和（J）的去铁胱醇类似物的方法和药物组合物，用于治疗和/或预防这些病理条件、金属（如铁、铝、镧系元素或锕系元素（如铀））过载症状和传染病（如疟疾）。

  公开号：

  WO2015077655A1

文献信息

• [EN] DESFERRITHIOCIN ANALOGS AND USES THEREOF<br/>[FR] ANALOGUES DE LA DESFERRITHIOCINE ET LEURS UTILISATIONS
  申请人：UNIV FLORIDA

  公开号：WO2015077655A1

  公开（公告）日：2015-05-28

  Iron overload is associated with pathological conditions such as oxidative stress, transfusional iron overload, thalassemia, primary hemochromatosis, secondary hemochromatosis, diabetes, liver disease, heart disease, cancer, radiation injury, neurological or neurodegenerative disorder, Friedreich's ataxia (FRDA), macular degeneration, closed head injury, irritable bowel disease, and reperfusion injury. The present invention provides methods and pharmaceutical compositions using desferrithiocin analogs of Formulae (A) and (J) for treating and/or preventing these pathological conditions, metal (e.g., iron, aluminum, a lanthanide, or an actinide (e.g., uranium)) overload conditions, and infectious diseases (e.g., malaria).

  铁过载与病理条件相关，如氧化应激、输血性铁过载、地中海贫血、原发性血色病、继发性血色病、糖尿病、肝病、心脏病、癌症、放射损伤、神经或神经退行性疾病、弗里德雷希共济失调（FRDA）、黄斑变性、闭合性头部损伤、肠易激综合征和再灌注损伤。本发明提供使用式（A）和（J）的去铁胱醇类似物的方法和药物组合物，用于治疗和/或预防这些病理条件、金属（如铁、铝、镧系元素或锕系元素（如铀））过载症状和传染病（如疟疾）。
• Desferrithiocin analogs and uses thereof
  申请人：University of Florida Research Foundation, Incorporated

  公开号：US10010535B2

  公开（公告）日：2018-07-03

  Iron overload is associated with pathological conditions such as oxidative stress, transfusional iron overload, thalassemia, primary hemochromatosis, secondary hemochromatosis, diabetes, liver disease, heart disease, cancer, radiation injury, neurological or neurodegenerative disorder, Friedreich's ataxia (FRDA), macular degeneration, closed head injury, irritable bowel disease, and reperfusion injury. The present invention provides methods and pharmaceutical compositions using desferrithiocin analogs of Formulae (A) and (J) for treating and/or preventing these pathological conditions, metal (e.g., iron, aluminum, a lanthanide, or an actinide (e.g., uranium)) overload conditions, and infectious diseases (e.g., malaria).

  铁超载与氧化应激、输血铁超载、地中海贫血、原发性血色素沉着病、继发性血色素沉着病、糖尿病、肝病、心脏病、癌症、辐射损伤、神经或神经退行性疾病、弗里德里希共济失调（FRDA）、黄斑变性、闭合性头部损伤、肠易激性疾病和再灌注损伤等病理状况有关。本发明提供了使用式（A）和式（J）的去铁硫霉素类似物治疗和/或预防这些病理状况、金属（如铁、铝、镧系元素或锕系元素（如铀））过载状况和传染病（如疟疾）的方法和药物组合物。
• DESFERRITHIOCIN ANALOGS AND USES THEREOF
  申请人：University of Florida Research Foundation, Inc.

  公开号：EP3071201A1

  公开（公告）日：2016-09-28
• Substituent Effects on Desferrithiocin and Desferrithiocin Analogue Iron-Clearing and Toxicity Profiles
  作者：Raymond J. Bergeron、Jan Wiegand、Neelam Bharti、James S. McManis

  DOI：10.1021/jm300509y

  日期：2012.8.23

  Desferrithiocin (DFT, 1) is a very efficient iron chelator when given orally. However, it is severely nephrotoxic. Structure-activity studies with 1 demonstrated that removal of the aromatic nitrogen to provide desazadesferrithiocin (DADFT, 2) and introduction of either a hydroxyl group or a polyether fragment onto the aromatic ring resulted in orally active iron chelators that were much less toxic than 1. The purpose of the current study was to determine if a comparable reduction in renal toxicity could be achieved by performing the same structural manipulations on 1 itself. Accordingly, three DFT analogues were synthesized. The iron-clearing efficiency and ferrokinetics were evaluated in rats and primates; toxicity assessments were carried out in rodents. The resulting DFT ligands demonstrated a reduction in toxicity that was equivalent to that of the DADFT analogues and presented with excellent iron-clearing properties.