desferrithiocin | 105635-69-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: desferrithiocin
• 英文别名: Desferrithiocin；sodium;(4S)-2-(3-hydroxypyridin-2-yl)-4-methyl-5H-1,3-thiazole-4-carboxylate
• CAS: 105635-69-6
• 化学式: C₁₀H₉N₂O₃S*Na
• 分子量: 260.249
• InChiKey: UGJSEILLHZKUBG-HNCPQSOCSA-M

物化性质

• 熔点：
  154 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  desferrithiocin 在 盐酸 作用下， 反应 144.0h， 以53%的产率得到N-(3'-hydroxypyridin-2'-oyl)-D-α-methylcysteine
  参考文献：
  名称：

  Bergeron; Wollenweber; Wiegand, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2889 - 2895

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-4,5-dihydro-2-(3-hydroxy-2-pyridinyl)-4-methyl-4-thiazolecarboxylic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 desferrithiocin
  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）。
• 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.
• Bergeron; Wollenweber; Wiegand, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2889 - 2895
  作者：Bergeron、Wollenweber、Wiegand

  DOI：——

  日期：——