3-(Adamant-1-ylmethylenoxycarbonyl)phthalimide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-(Adamant-1-ylmethylenoxycarbonyl)phthalimide
• 英文别名: 1-Adamantylmethyl 1,3-dioxoisoindole-5-carboxylate
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: BFJQRLYSCPTRRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  齐多夫定 、 3-(Adamant-1-ylmethylenoxycarbonyl)phthalimide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 12.0h， 以65%的产率得到1-adamantylmethyl 2-[[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl]-1,3-dioxo-isoindoline-5-carboxylate
  参考文献：
  名称：

  Tumor necrosis factor-alpha production-regulating activity of phthalimide derivatives in genetically modified murine melanoma cells B78H1

  摘要：

  The effect of imides, monothioimides, trimellitimides, as well as 5'-deoxy-5'-phthaloylamino-derivatives of azidothymidine on tumor necrosis factor-alpha (TNF-alpha) production by genetically modified murine B78H1 melanoma cells transduced with the gene for human TNF-alpha (B78/TNF) was investigated. It was found that N-(adamant-1-yl)monothiophthalimide (1e) and N-(adamant-2-yl)-monothiophthalimide (1f) showed over 200% enhancing of TNF-alpha production while some of imides were inhibitors.

  DOI：

  10.1016/s0014-827x(03)00049-1
• 作为产物：
  描述：

  4-(Adamant-1-ylmethylenoxycarbonyl)phthalanhydride 在 尿素 作用下， 反应 0.17h， 以78%的产率得到3-(Adamant-1-ylmethylenoxycarbonyl)phthalimide
  参考文献：
  名称：

  Synthesis and antimicrobial activity of new adamantane derivatives II

  摘要：

  A series of new derivatives of adamantane was synthesised. The new compound 4-(adamant-1-ylethylenoxycarbonyl)phthalanhydride obtained from 1-adamantaneethanol and trimellitic anhydride chloride, as well as 4-(adamant-1-ylmethylenoxycarbonyl)phthalanhydride, appeared very useful for preparation of a number of N-substituted phthalimides. Antimicrobial activity of newly obtained derivatives such as, for example, 4-(adamant-1-ylethylenoxycarbonyl)-N-(L-phenylalanyl)phthalimide or 4-(adamant-1-ylmethylenoxycarbonyl)-N-(L-leucyl)-phtalimide was tested against Staphylococcus aureus, Bacillus sp., Micrococcus flavus and Enterococcus faecium. The minimal inhibitory concentrations for these compounds against Bacillus cereus were 15 and 8 mug/ml, respectively. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00075-6

文献信息

• Synthesis and antimicrobial activity of new adamantane derivatives II
  作者：Andrzej Orzeszko、Beata Kamińska、Grażyna Orzeszko、Bohdan J. Starościak

  DOI：10.1016/s0014-827x(00)00075-6

  日期：2000.11

  A series of new derivatives of adamantane was synthesised. The new compound 4-(adamant-1-ylethylenoxycarbonyl)phthalanhydride obtained from 1-adamantaneethanol and trimellitic anhydride chloride, as well as 4-(adamant-1-ylmethylenoxycarbonyl)phthalanhydride, appeared very useful for preparation of a number of N-substituted phthalimides. Antimicrobial activity of newly obtained derivatives such as, for example, 4-(adamant-1-ylethylenoxycarbonyl)-N-(L-phenylalanyl)phthalimide or 4-(adamant-1-ylmethylenoxycarbonyl)-N-(L-leucyl)-phtalimide was tested against Staphylococcus aureus, Bacillus sp., Micrococcus flavus and Enterococcus faecium. The minimal inhibitory concentrations for these compounds against Bacillus cereus were 15 and 8 mug/ml, respectively. (C) 2000 Elsevier Science S.A. All rights reserved.
• Tumor necrosis factor-alpha production-regulating activity of phthalimide derivatives in genetically modified murine melanoma cells B78H1
  作者：A Orzeszko

  DOI：10.1016/s0014-827x(03)00049-1

  日期：2003.5

  The effect of imides, monothioimides, trimellitimides, as well as 5'-deoxy-5'-phthaloylamino-derivatives of azidothymidine on tumor necrosis factor-alpha (TNF-alpha) production by genetically modified murine B78H1 melanoma cells transduced with the gene for human TNF-alpha (B78/TNF) was investigated. It was found that N-(adamant-1-yl)monothiophthalimide (1e) and N-(adamant-2-yl)-monothiophthalimide (1f) showed over 200% enhancing of TNF-alpha production while some of imides were inhibitors.