(E)-2-(3-methyl-5-styrylisoxazol-4-yl)-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione | 1443511-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-(3-methyl-5-styrylisoxazol-4-yl)-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione
• 英文别名: 2-[3-methyl-5-[(E)-2-phenylethenyl]-1,2-oxazol-4-yl]spiro[1H-benzo[f]isoindole-3,3'-1H-indole]-2',4,9-trione
• CAS: 1443511-63-4
• 化学式: C₃₁H₂₁N₃O₄
• 分子量: 499.525
• InChiKey: DXVVQCRTKVYVEI-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  92.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-amino-3-methyl-5-styrylisoxazole 在 ammonium cerium (IV) nitrate 、 氧气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E)-2-(3-methyl-5-styrylisoxazol-4-yl)-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione
  参考文献：
  名称：

  A facile synthesis, anti-inflammatory and analgesic activity of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3′-indoline]-2′,4,9-triones

  摘要：

  A new series of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-triones (14) were synthesized by reaction of 4-amino-3-methyl-5-styrylisoxazole 10 with chloroacetic acid followed by a three component reaction with substituted isatins 12 and 1,4-naphthoquinone 13 using Ceric ammonium nitrate (CAN) catalyst under aerial oxidation condition. Structures of these compounds were established on the basis of IR, H-1 NMR, C-13 NMR and mass spectral data. The title compounds 14a-j were evaluated for their anti-inflammatory and analgesic activity. Compounds 14d, 14e and 14f exhibited potent anti-inflammatory and analgesic activity as that of standard drugs. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.053

文献信息

• A facile synthesis, anti-inflammatory and analgesic activity of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3′-indoline]-2′,4,9-triones
  作者：E. Rajanarendar、S. Ramakrishna、K. Govardhan Reddy、D. Nagaraju、Y.N. Reddy

  DOI：10.1016/j.bmcl.2013.04.053

  日期：2013.7

  A new series of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-triones (14) were synthesized by reaction of 4-amino-3-methyl-5-styrylisoxazole 10 with chloroacetic acid followed by a three component reaction with substituted isatins 12 and 1,4-naphthoquinone 13 using Ceric ammonium nitrate (CAN) catalyst under aerial oxidation condition. Structures of these compounds were established on the basis of IR, H-1 NMR, C-13 NMR and mass spectral data. The title compounds 14a-j were evaluated for their anti-inflammatory and analgesic activity. Compounds 14d, 14e and 14f exhibited potent anti-inflammatory and analgesic activity as that of standard drugs. (c) 2013 Elsevier Ltd. All rights reserved.