2-(benzyloxy)-1-naphthamide | 175293-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(benzyloxy)-1-naphthamide
• 英文别名: 2-Phenylmethoxynaphthalene-1-carboxamide
• CAS: 175293-39-7
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: JFCPLPMDQXVPSL-UHFFFAOYSA-N

物化性质

• 沸点：
  495.6±28.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)-1-naphthamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 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
• 作为产物：
  描述：

  2-苄氧基-1-萘醛 在 ammonium hydroxide 、 sodium chlorite 、 草酰氯 、 氨基磺酸 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 25.5h， 生成 2-(benzyloxy)-1-naphthamide
  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.

  已经制备了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
• Synthesis and Biological Evaluation of Naphthyldesferrithiocin Iron Chelators
  作者：Raymond J. Bergeron、Jan Wiegand、Markus Wollenweber、James S. McManis、Samuel E. Algee、Katie Ratliff-Thompson

  DOI：10.1021/jm9508752

  日期：1996.1.1

  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.