5-Benzoyl-8a-hydroxyspiro[2,4-dihydro-1,4-benzoxazine-3,1'-cyclopentane]-8-one | 251562-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 5-Benzoyl-8a-hydroxyspiro[2,4-dihydro-1,4-benzoxazine-3,1'-cyclopentane]-8-one
• CAS: 251562-04-6
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: IZGIXOCAYPNJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Benzoyl-8a-hydroxyspiro[2,4-dihydro-1,4-benzoxazine-3,1'-cyclopentane]-8-one 在 高氯酸四乙基铵 作用下， 以 甲醇 为溶剂， 以80%的产率得到(8-Hydroxyspiro[2,4-dihydro-1,4-benzoxazine-3,1'-cyclopentane]-5-yl)-phenylmethanone
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of New 8-Amino-1,4-benzoxazine Derivatives as Neuroprotective Antioxidants

  摘要：

  A series of new 8-amino-1,4-benzoxazine derivatives 5a-o was synthesized and examined for their intrinsic cytotoxicity and their capacity to inhibit oxidative stress-mediated neuronal degeneration in neuronal cell cultures. In particular, substituent effects at the 3- and 8-positions of the 1,4-benzoxazine ring were investigated by in vitro evaluation.. In this aim, 3-alkyl substituents seemed to be essential for efficient neuroprotective activity. Furthermore, within the subseries of substituted S-alkyl benzoxazines, the most active derivatives were those bearing an 8-benzylamino substituent. From the combined results of both toxicity and neuroprotection expressed in terms of the safety index, 8-benzylamino-substituted-3-alkyl-1,4-benzoxazines were identified as the most promising compounds, owing to their potent neuroprotective activity without the manifestation of intrinsic cytotoxicity.

  DOI：

  10.1021/jm991105j
• 作为产物：
  描述：

  1-氨基-1-环戊基甲醇 、 (3,4-dihydroxy-2-methoxyphenyl) (phenyl) methanone 在 高氯酸四乙基铵 作用下， 以 甲醇 为溶剂， 以60%的产率得到5-Benzoyl-8a-hydroxyspiro[2,4-dihydro-1,4-benzoxazine-3,1'-cyclopentane]-8-one
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of New 8-Amino-1,4-benzoxazine Derivatives as Neuroprotective Antioxidants

  摘要：

  A series of new 8-amino-1,4-benzoxazine derivatives 5a-o was synthesized and examined for their intrinsic cytotoxicity and their capacity to inhibit oxidative stress-mediated neuronal degeneration in neuronal cell cultures. In particular, substituent effects at the 3- and 8-positions of the 1,4-benzoxazine ring were investigated by in vitro evaluation.. In this aim, 3-alkyl substituents seemed to be essential for efficient neuroprotective activity. Furthermore, within the subseries of substituted S-alkyl benzoxazines, the most active derivatives were those bearing an 8-benzylamino substituent. From the combined results of both toxicity and neuroprotection expressed in terms of the safety index, 8-benzylamino-substituted-3-alkyl-1,4-benzoxazines were identified as the most promising compounds, owing to their potent neuroprotective activity without the manifestation of intrinsic cytotoxicity.

  DOI：

  10.1021/jm991105j

文献信息

• Synthesis and in Vitro Evaluation of New 8-Amino-1,4-benzoxazine Derivatives as Neuroprotective Antioxidants
  作者：Martine Largeron、Brian Lockhart、Bruno Pfeiffer、Maurice-Bernard Fleury

  DOI：10.1021/jm991105j

  日期：1999.12.2

  A series of new 8-amino-1,4-benzoxazine derivatives 5a-o was synthesized and examined for their intrinsic cytotoxicity and their capacity to inhibit oxidative stress-mediated neuronal degeneration in neuronal cell cultures. In particular, substituent effects at the 3- and 8-positions of the 1,4-benzoxazine ring were investigated by in vitro evaluation.. In this aim, 3-alkyl substituents seemed to be essential for efficient neuroprotective activity. Furthermore, within the subseries of substituted S-alkyl benzoxazines, the most active derivatives were those bearing an 8-benzylamino substituent. From the combined results of both toxicity and neuroprotection expressed in terms of the safety index, 8-benzylamino-substituted-3-alkyl-1,4-benzoxazines were identified as the most promising compounds, owing to their potent neuroprotective activity without the manifestation of intrinsic cytotoxicity.