5-azido-1,3-dioxy-1H-benz(de)isoquinoline-2(3H)-acetic acid methyl ester | 103884-85-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-azido-1,3-dioxy-1H-benz(de)isoquinoline-2(3H)-acetic acid methyl ester
• 英文别名: (5-Azido-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetic acid methyl ester；methyl 2-(5-azido-1,3-dioxobenzo[de]isoquinolin-2-yl)acetate
• CAS: 103884-85-1
• 化学式: C₁₅H₁₀N₄O₄
• 分子量: 310.269
• InChiKey: OZSHHPCNJSASRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-azido-1,3-dioxy-1H-benz(de)isoquinoline-2(3H)-acetic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以47%的产率得到5-叠氮基阿司他丁
  参考文献：
  名称：

  Synthesis and biological evaluation of irreversible inhibitors of aldose reductase

  摘要：

  5-Isothiocyanatoalrestatin (1b) and 5-azidoalrestatin (1c) were prepared synthetically and examined as potential affinity and photoaffinity inhibitors of rat lens aldose reductase. Both compound 1b and 1c under appropriate conditions at 10(-4) M produced a 70% irreversible inactivation of aldose reductase within 1 min. The enzyme could, in part, be protected by preincubation with sorbinil 2, a known potent inhibitor of aldose reductase.

  DOI：

  10.1021/jm00161a040
• 作为产物：
  描述：

  5-amino-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid methyl ester 在 盐酸 、 sodium azide 、 sodium nitrite 作用下， 生成 5-azido-1,3-dioxy-1H-benz(de)isoquinoline-2(3H)-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of irreversible inhibitors of aldose reductase

  摘要：

  5-Isothiocyanatoalrestatin (1b) and 5-azidoalrestatin (1c) were prepared synthetically and examined as potential affinity and photoaffinity inhibitors of rat lens aldose reductase. Both compound 1b and 1c under appropriate conditions at 10(-4) M produced a 70% irreversible inactivation of aldose reductase within 1 min. The enzyme could, in part, be protected by preincubation with sorbinil 2, a known potent inhibitor of aldose reductase.

  DOI：

  10.1021/jm00161a040

文献信息

• ARES J. J.; KADOR P. F.; MILLER D. D., J. MED. CHEM., 29,(1986) N 11, 2384-2389
  作者：ARES J. J.、 KADOR P. F.、 MILLER D. D.

  DOI：——

  日期：——