Methyl 2-[2-(azidomethyl)-5-phenylmethoxyphenyl]acetate | 252061-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 2-[2-(azidomethyl)-5-phenylmethoxyphenyl]acetate
• CAS: 252061-86-2
• 化学式: C₁₇H₁₇N₃O₃
• 分子量: 311.34
• InChiKey: PPSMLLMFCZDPNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-[2-(azidomethyl)-5-phenylmethoxyphenyl]acetate 在 palladium on activated charcoal 氢气 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 tert-butyl 2-[6-[[4-[N'-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]phenyl]methoxy]-3-oxo-1,4-dihydroisoquinolin-2-yl]acetate
  参考文献：
  名称：

  Fused Bicyclic Gly-Asp β-Turn Mimics with Specific Affinity for GPIIb-IIIa

  摘要：

  Disubstituted isoquinolones 2 and 3 have affinity for GPIIb-IIIa and represent leads for further structural evaluation. Structure-activity studies centered on the bicyclic beta-turn mimic contained in these molecules indicated that this moiety could accommodate a variety of modifications. Specifically, monocyclic, 6,5-bicyclic, and 6,7-bicyclic structures provide compounds with affinity for GPIIb-IIIa. Within the 6,6-series, isoquinoline, tetralin, tetralone, and benzopyran nuclei yield potent antagonists that are specific for GPIIb-IIIa. Attachment of the arginine isostere (benzamidine) to the supporting nucleus can be accomplished with an ether or amide linkage, although the latter enhances activity. Several compounds in this series provided measurable blood levels after oral dosing. Conversion of the acid moiety in these molecules to an ester generally provided compounds which gave greater systemic exposure after oral administration. Absolute bioavailabilities in the rat for the ethyl ester prodrug derivatives of the tetralin, tetralone, and benzopyran analogues of 3 were 28%, 23%, and 24%, respectively.

  DOI：

  10.1021/jm990365y
• 作为产物：
  描述：

  Methyl 2-[2-(bromomethyl)-5-phenylmethoxyphenyl]acetate 在 叠氮化锂 作用下， 生成 Methyl 2-[2-(azidomethyl)-5-phenylmethoxyphenyl]acetate
  参考文献：
  名称：

  Fused Bicyclic Gly-Asp β-Turn Mimics with Specific Affinity for GPIIb-IIIa

  摘要：

  Disubstituted isoquinolones 2 and 3 have affinity for GPIIb-IIIa and represent leads for further structural evaluation. Structure-activity studies centered on the bicyclic beta-turn mimic contained in these molecules indicated that this moiety could accommodate a variety of modifications. Specifically, monocyclic, 6,5-bicyclic, and 6,7-bicyclic structures provide compounds with affinity for GPIIb-IIIa. Within the 6,6-series, isoquinoline, tetralin, tetralone, and benzopyran nuclei yield potent antagonists that are specific for GPIIb-IIIa. Attachment of the arginine isostere (benzamidine) to the supporting nucleus can be accomplished with an ether or amide linkage, although the latter enhances activity. Several compounds in this series provided measurable blood levels after oral dosing. Conversion of the acid moiety in these molecules to an ester generally provided compounds which gave greater systemic exposure after oral administration. Absolute bioavailabilities in the rat for the ethyl ester prodrug derivatives of the tetralin, tetralone, and benzopyran analogues of 3 were 28%, 23%, and 24%, respectively.

  DOI：

  10.1021/jm990365y