2-(benzyloxy)naphthalene-1-carboxyl chloride | 175293-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(benzyloxy)naphthalene-1-carboxyl chloride
• 英文别名: 2-Phenylmethoxynaphthalene-1-carbonyl chloride
• CAS: 175293-38-6
• 化学式: C₁₈H₁₃ClO₂
• 分子量: 296.753
• InChiKey: KKZOBWRZYKFFRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)naphthalene-1-carboxyl chloride 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 54.0h， 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 sodium chlorite 、 草酰氯 、 氨基磺酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 1.02h， 生成 2-(benzyloxy)naphthalene-1-carboxyl chloride
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l

文献信息

• Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis
  作者：Kevin J. Duffy、Michael G. Darcy、Evelyne Delorme、Susan B. Dillon、Daniel F. Eppley、Connie Erickson-Miller、Leslie Giampa、Christopher B. Hopson、Yifang Huang、Richard M. Keenan、Peter Lamb、Lynnette Leong、Nannan Liu、Stephen G. Miller、Alan T. Price、Jon Rosen、Rakhi Shah、Tony N. Shaw、Heather Smith、Kenneth C. Stark、Shin-Shay Tian、Curtis Tyree、Kenneth J. Wiggall、Lily Zhang、Juan I. Luengo

  DOI：10.1021/jm010283l

  日期：2001.10.1

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.
• 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.