ethyl 2-hydroxy-1-naphthimidate | 175293-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2-hydroxy-1-naphthimidate
• 英文别名: ethyl 2-hydroxynaphthalene-1-carboximidate
• CAS: 175293-37-5
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: VPDABOROMJYOPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  53.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-1-naphthimidate 、 D-cysteine 以 甲醇 为溶剂， 反应 46.0h， 生成 (4S)-2-(2-hydroxynaphthalen-1-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Naphthyldesferrithiocin Iron Chelators

  摘要：

  The synthesis and iron-clearing properties of the naphthyldesferrithiocins 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid, 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, and 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid are described. While the bile duct-cannulated rat model clearly demonstrates that the 3'-hydroxynaphthyl-2'-yl compounds are orally active iron-clearing agents and the corresponding 2'-hydroxynaphthyl-1'-yl compounds are not, in the primate model none of the bent-fused desazadesferrithiocin analogues are active. Oral versus subcutaneous administration of these ligands strongly suggests that metabolism is a key issue in their iron-clearing properties and that these bent-fused desferrithiocins are not good candidates for orally active iron-clearing drugs.

  DOI：

  10.1021/jm9508752
• 作为产物：
  描述：

  2-苄氧基-1-萘醛 在 palladium on activated charcoal ammonium hydroxide 、 sodium chlorite 、 草酰氯 、 氨基磺酸 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 55.5h， 生成 ethyl 2-hydroxy-1-naphthimidate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Naphthyldesferrithiocin Iron Chelators

  摘要：

  The synthesis and iron-clearing properties of the naphthyldesferrithiocins 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid, 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, and 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid are described. While the bile duct-cannulated rat model clearly demonstrates that the 3'-hydroxynaphthyl-2'-yl compounds are orally active iron-clearing agents and the corresponding 2'-hydroxynaphthyl-1'-yl compounds are not, in the primate model none of the bent-fused desazadesferrithiocin analogues are active. Oral versus subcutaneous administration of these ligands strongly suggests that metabolism is a key issue in their iron-clearing properties and that these bent-fused desferrithiocins are not good candidates for orally active iron-clearing drugs.

  DOI：

  10.1021/jm9508752

文献信息

• Thiazoline acid derivatives
  申请人：University of Florida Research Foundation, Inc.

  公开号：US05840739A1

  公开（公告）日：1998-11-24

  Thiazoline acids and derivatives useful as chelators of trivalent metals in therapeutic applications have been prepared.

  已经制备出可用作治疗应用中三价金属螯合剂的噻唑酸及其衍生物。
• [EN] THIAZOLINE ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDE DE THIAZOLINE
  申请人：UNIVERSITY OF FLORIDA

  公开号：WO1997036885A1

  公开（公告）日：1997-10-09

  (EN) 2-(2-Hydroxy aryl)-thiazoline-4-carboxylic acids and derivatives are useful as chelators of trivalent metals in therapeutic applications.(FR) L'invention a pour objet des acides 2-(2-hydroxy aryl)-thiazoline-4-carboxyliques et leurs dérivés, qui sont utiles comme chélatants de métaux trivalents dans des applications thérapeutiques.

  2-(2-羟基苯基)噻唑线-4-酸和衍生物，在治疗应用中，它们作为三价金属的配位剂有用。
• THIAZOLINE ACID DERIVATIVES
  申请人：UNIVERSITY OF FLORIDA

  公开号：EP0900209A1

  公开（公告）日：1999-03-10
• US5840739A
  申请人：——

  公开号：US5840739A

  公开（公告）日：1998-11-24