4-amino-6-fluoro-3,4-dihydro-2H-1-benzopyran-4-acetic acid ethyl ester | 131436-64-1

• 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: 4-amino-6-fluoro-3,4-dihydro-2H-1-benzopyran-4-acetic acid ethyl ester
• 英文别名: ethyl 2-(4-amino-6-fluoro-2,3-dihydrochromen-4-yl)acetate
• CAS: 131436-64-1
• 化学式: C₁₃H₁₆FNO₃
• 分子量: 253.273
• InChiKey: ADXSXPLGWHZMPM-UHFFFAOYSA-N

物化性质

• 密度：
  1.197±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-6-fluoro-3,4-dihydro-2H-1-benzopyran-4-acetic acid ethyl ester 、 草酸二乙酯 以84%的产率得到
  参考文献：
  名称：

  MYLARI, BANAVARA L.;BEYER, THOMAS A.;SIEGEL, TODD W., J. MED. CHEM., 34,(1991) N, C. 1011-1018

  摘要：

  DOI：
• 作为产物：
  描述：

  6-fluoro-3,4-dihydro-4-<<<(4-methoxyphenyl)methoxy>carbonyl>amino>-2H-1-benzopyran-4-acetic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以14%的产率得到4-amino-6-fluoro-3,4-dihydro-2H-1-benzopyran-4-acetic acid ethyl ester
  参考文献：
  名称：

  A highly specific aldose reductase inhibitor, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate and its congeners

  摘要：

  Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate (1, EBPC) is a potent and specific inhibitor of aldose reductase. It was > 4000 x more potent in its inhibition of rat lens aldose reductase than the closely related rat or pig kidney aldehyde reductase, thus making it the most selective inhibitor of a NADPH-dependent carbonyl reductase identified to date. In agreement with this observation, it was found to be a highly potent inhibitor of aldose reductase from rat sciatic nerve with > 98% inhibition at 1-mu-M, but it was practically devoid of activity against aldehyde reductases from rat liver and brain. Inhibition of aldose reductase was mixed type for glyceraldehyde (K(i) = 8.0 x 10(-8) M) and noncompetitive for NADPH (K(i) = 1.70 x 10(-8) M). Its potential as an in vitro tool to quantitate monomeric aldo/keto reductase activities in crude tissue extracts is presented. Structure-activity relationships emerging from synthetic modifications of EBPC are discussed. Several modifications were found to be active in vitro against aldose reductase from human placenta and in vivo in a rat model of diabetic complications, but none was more potent than EBPC.

  DOI：

  10.1021/jm00107a020