2-hydroxy-3-(3,6-dioxaheptyloxy)benzonitrile | 1346427-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hydroxy-3-(3,6-dioxaheptyloxy)benzonitrile
• 英文别名: 2-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)benzonitrile；2-hydroxy-3-[2-(2-methoxyethoxy)ethoxy]benzonitrile
• CAS: 1346427-97-1
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: ZLBVXXUNQNZXIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-(3,6-dioxaheptyloxy)benzonitrile 在 盐酸 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 methyl 2-(2-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4,5-dihydro-1H-imidazole-4-carboxylate
  参考文献：
  名称：

  DESAZADESFERROTHIOCIN AND DESAZADESFERROTHIOCIN POLYETHER ANALOGUES AS METAL CHELATION AGENTS

  摘要：

  本文披露了新的去氮去除铁硫胺聚醚（DADFT-PE）类似物化合物，以及包含它们的药物组合物，以及它们作为金属螯合剂用于治疗疾病的应用。还提供了在人类或动物主体中螯合铁和其他金属的方法，用于治疗金属过载和中毒。

  公开号：

  US20110275636A1
• 作为产物：
  描述：

  2,3-二羟基苯甲腈 、 2-(2-甲氧基乙氧基)乙基4-甲基苯磺酸负离子 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 2.0h， 以25%的产率得到2-hydroxy-3-(3,6-dioxaheptyloxy)benzonitrile
  参考文献：
  名称：

  DESAZADESFERROTHIOCIN AND DESAZADESFERROTHIOCIN POLYETHER ANALOGUES AS METAL CHELATION AGENTS

  摘要：

  本文披露了新的去氮去除铁硫胺聚醚（DADFT-PE）类似物化合物，以及包含它们的药物组合物，以及它们作为金属螯合剂用于治疗疾病的应用。还提供了在人类或动物主体中螯合铁和其他金属的方法，用于治疗金属过载和中毒。

  公开号：

  US20110275636A1

文献信息

• Desazadesferrothiocin and desazadesferrothiocin polyether analogues as metal chelation agents
  申请人：Malecha James

  公开号：US09045440B2

  公开（公告）日：2015-06-02

  Disclosed herein are new compounds of desazadesferrothiocin polyether (DADFT-PE) analogs, as well as pharmaceutical compositions comprising them and their application as metal chelation agents for the treatment of disease. Methods of chelation of iron and other metals in a human or animal subject are also provided for the treatment of metal overload and toxicity.

  本文揭示了新的去氮去硫亚德斯费罗替西汀聚醚（DADFT-PE）类似物化合物，以及包含它们的药物组合物，并将它们应用于金属螯合剂治疗疾病。还提供了在人类或动物主体中螯合铁和其他金属以治疗金属过载和毒性的方法。
• DESAZADESFERROTHIOCIN ANALOGUES AS METAL CHELATION AGENTS
  申请人：FerroKin BioSciences, Inc.

  公开号：US20150259306A1

  公开（公告）日：2015-09-17

  Disclosed herein are new compounds of desazadesferrothiocin polyether (DADFT-PE) analogues, as well as pharmaceutical compositions comprising them and their application as metal chelation agents for the treatment of disease. Methods of chelation of iron and other metals in a human or animal subject are also provided for the treatment of metal overload and toxicity.

  本文披露了新的去氮去铁硫单环醚（DADFT-PE）类似物化合物，以及包含它们的制药组合物，以及它们作为金属螯合剂用于治疗疾病的应用。还提供了用于治疗人类或动物主体中金属过载和毒性的铁和其他金属螯合方法。
• Desferrithiocin analogue iron chelators: iron clearing efficiency, tissue distribution, and renal toxicity
  作者：Raymond J. Bergeron、Jan Wiegand、Neelam Bharti、James S. McManis、Shailendra Singh

  DOI：10.1007/s10534-010-9389-y

  日期：2011.4

  The current solution to iron-mediated damage in transfusional iron overload disorders is decorporation of excess unmanaged metal, chelation therapy. The clinical development of the tridentate chelator deferitrin (1, Table 1) was halted due to nephrotoxicity. It was then shown by replacing the 4'-(HO) of 1 with a 3,6,9-trioxadecyloxy group, the nephrotoxicity could be ameliorated. Further structure-activity relationship studies have established that the length and the position of the polyether backbone controlled: (1) the ligand's iron clearing efficiency (ICE), (2) chelator tissue distribution, (3) biliary ferrokinetics, and (4) tissue iron reduction. The current investigation compares the ICE and tissue distribution of a series of (S)-4,5-dihydro-2-[2-hydroxy-4-(polyether)phenyl]-4-methyl-4-thiazolecarboxylic acids (Table 1, 3-5) and the (S)-4,5-dihydro-2-[2-hydroxy-3-(polyether)phenyl]-4-methyl-4-thiazolecarboxylic acids (Table 1, 8-10). The three most effective polyether analogues, in terms of performance ratio (PR), defined as mean ICEprimate/ICErodent, are 3 (PR 1.1), 8, (PR 1.5), and 9, now in human trials, (PR 2.2). At the onset of the clinical trial on 9, no data were available for ligand 3 or 8. This is unfortunate, as 3 has many advantages over 9, e.g., the ICE of 3 in rats is 2.5-fold greater than that of 9 and analogue 3 achieves very high levels in the liver, pancreas, and heart, the organs most affected by iron overload. Finally, the impact of 3 on the urinary excretion of kidney injury molecule-1 (Kim-1), an early diagnostic biomarker for monitoring acute kidney toxicity, has been carried out in rats; no evidence of nephrotoxicity was found. Overall, the results suggest that 3 would be a far superior clinical candidate to 9.
• US9045440B2
  申请人：——

  公开号：US9045440B2

  公开（公告）日：2015-06-02
• [EN] DESAZADESFERROTHIOCIN AND DESAZADESFERROTHIOCIN POLYETHER ANALOGUES AS METAL CHELATION AGENTS<br/>[FR] ANALOGUES DE DÉSAZADESFERROTHIOCINE ET DE POLYÉTHER DE DÉSAZADESFERROTHIOCINE UTILISÉS EN TANT QUE CHÉLATEURS MÉTALLIQUES
  申请人：FERROKIN BIOSCIENCES INC

  公开号：WO2011140232A2

  公开（公告）日：2011-11-10

  Disclosed herein are new compounds of desazadesferrothiocin polyether (DADFT- PE) analogues, as well as pharmaceutical compositions comprising them and their application as metal chelation agents for the treatment of disease. Methods of chelation of iron and other metals in a human or animal subject are also provided for the treatment of metal overload and toxicity.