3-{2-[3(S)-allyl-5-methoxy-1-methyl-2-oxoindolin-3-yl]acetyl}-4(R)-phenyloxazolidin-2-one | 1396316-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-{2-[3(S)-allyl-5-methoxy-1-methyl-2-oxoindolin-3-yl]acetyl}-4(R)-phenyloxazolidin-2-one
• CAS: 1396316-92-9
• 化学式: C₂₄H₂₄N₂O₅
• 分子量: 420.465
• InChiKey: WQKWSVAYNLGJIC-RDPSFJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-{2-[3(S)-allyl-5-methoxy-1-methyl-2-oxoindolin-3-yl]acetyl}-4(R)-phenyloxazolidin-2-one 在 lithium hydroxide monohydrate 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以89%的产率得到(S)-2-(3-allyl-5-methoxy-1-methyl-2-oxoindolin-3-yl)acetic acid
  参考文献：
  名称：

  Synthesis of phenserine analogues and evaluation of their cholinesterase inhibitory activities

  摘要：

  Phenserine is a potentially attractive drug for Alzheimer's disease. In order to further expand SAR study for inhibitions of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), the methyl group at the 3a-position of phenserine was replaced with an alkyl or alkenyl group, and its phenylcarbamoyl moiety was substituted at the o- or p-position. The synthetic methodology for these phenserine analogues includes the efficient cascade reactions for introduction of the 3a-substituent and assembly of the quaternary carbon center followed by reductive cyclization to the key pyrroloindoline structure. The bulkiness of the substituent at 3a-position of phenserine derivatives tends to reduce the inhibitory effect on AChE activity in the following order: methyl > ethyl > vinyl > propyl approximate to allyl > reverse-prenyl groups. Among the series synthesized, the 3a-ethyl derivative demonstrated the highest AChE selectivity. In construct, the 3a-reverse-prenyl derivative indicated modest BuChE selectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.048
• 作为产物：
  描述：

  1-乙酰基-5-甲氧基-2H-吲哚-3-酮 在 potassium tert-butylate 、 溴 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 104.0h， 生成 3-{2-[3(S)-allyl-5-methoxy-1-methyl-2-oxoindolin-3-yl]acetyl}-4(R)-phenyloxazolidin-2-one
  参考文献：
  名称：

  Synthesis of phenserine analogues and evaluation of their cholinesterase inhibitory activities

  摘要：

  Phenserine is a potentially attractive drug for Alzheimer's disease. In order to further expand SAR study for inhibitions of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), the methyl group at the 3a-position of phenserine was replaced with an alkyl or alkenyl group, and its phenylcarbamoyl moiety was substituted at the o- or p-position. The synthetic methodology for these phenserine analogues includes the efficient cascade reactions for introduction of the 3a-substituent and assembly of the quaternary carbon center followed by reductive cyclization to the key pyrroloindoline structure. The bulkiness of the substituent at 3a-position of phenserine derivatives tends to reduce the inhibitory effect on AChE activity in the following order: methyl > ethyl > vinyl > propyl approximate to allyl > reverse-prenyl groups. Among the series synthesized, the 3a-ethyl derivative demonstrated the highest AChE selectivity. In construct, the 3a-reverse-prenyl derivative indicated modest BuChE selectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.048