1,10b-dihydro-10-methoxy-3H-oxazolo[4,3-α]isoquinolin-3-one-5-carboxylic acid ethyl ester | 270251-58-6

• 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: 1,10b-dihydro-10-methoxy-3H-oxazolo[4,3-α]isoquinolin-3-one-5-carboxylic acid ethyl ester
• CAS: 270251-58-6
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: GNKDOJDRLNSZOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,10b-dihydro-10-methoxy-3H-oxazolo[4,3-α]isoquinolin-3-one-5-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以78%的产率得到10-Methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinoline-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of a netropsin conjugate of a water-soluble epi -quinocarcin analogue: the importance of stereochemistry at nitrogen

  摘要：

  The efficient synthesis of a water-soluble C11a-epi-analogue (6b) of quinocarcin is described. This substance, and a netropsin amide conjugate (8) lack the capacity to inflict oxidative damage on DNA due to the stereoelectronic geometry of their oxazolidine nitrogen atoms. The capacity of these substances to alkylate DNA through the generation of an iminium species has been examined. Both compounds were found to be unreactive as DNA alkylating agents. The results of this study are discussed in the context of previous proposals on the mode of action of this family of antitumor alkaloids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00314-4
• 作为产物：
  描述：

  6-Hydroxy-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinoline-5-carboxylic acid ethyl ester 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1,10b-dihydro-10-methoxy-3H-oxazolo[4,3-α]isoquinolin-3-one-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of a netropsin conjugate of a water-soluble epi -quinocarcin analogue: the importance of stereochemistry at nitrogen

  摘要：

  The efficient synthesis of a water-soluble C11a-epi-analogue (6b) of quinocarcin is described. This substance, and a netropsin amide conjugate (8) lack the capacity to inflict oxidative damage on DNA due to the stereoelectronic geometry of their oxazolidine nitrogen atoms. The capacity of these substances to alkylate DNA through the generation of an iminium species has been examined. Both compounds were found to be unreactive as DNA alkylating agents. The results of this study are discussed in the context of previous proposals on the mode of action of this family of antitumor alkaloids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00314-4