2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl 4-tert-butylbenzoate | 37710-55-7

• 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: 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl 4-tert-butylbenzoate
• 英文别名: 2-(1,3-dioxoisoindol-2-yl)ethyl 4-tert-butylbenzoate
• CAS: 37710-55-7
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: HCWJHJCUEYDZKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-羟乙基酞酰亚胺 、 对叔丁基苯甲酰氯 在 吡啶 、 四甲基乙二胺 作用下， 反应 18.0h， 以74%的产率得到2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl 4-tert-butylbenzoate
  参考文献：
  名称：

  (Hetero)aroyl esters of 2-(N-phthalimido)ethanol and analogues: parallel synthesis, anti-HIV-1 activity and cytotoxicity

  摘要：

  The structural simplification of the non-nucleoside reverse transcriptase inhibitors (NNRTIs) O-(2-phthalimidoethyl)-N-(hetero)aroyl-N-arylthiocarbamates led us to design (hetero)aroyl esters of 2-(N-phthalimido)ethanol as a potential new class of anti-HIV-1 agents. The setup of a solution-phase parallel synthesis method allowed the rapid preparation of a high number of analogues. In cell-based assays, 20 of 34 esters showed anti-HIV-1 activity ranging from nanomolar to micromolar concentrations. The most potent esters had only a minor effect or were ineffective in enzyme assay against HIV-1 reverse transcriptase. Variations on the O-(2-phthalimidoethyl) moiety led to compounds devoid of antiretroviral activity, but cytotoxic, in particular those bearing the 4-chloro-3-nitrobenzoyl moiety. The most cytotoxic compound displayed a CC50 value of 1.6 mu M.

  DOI：

  10.1007/s00044-009-9192-x

文献信息

• (Hetero)aroyl esters of 2-(N-phthalimido)ethanol and analogues: parallel synthesis, anti-HIV-1 activity and cytotoxicity
  作者：Sara Cesarini、Andrea Spallarossa、Angelo Ranise、Silvia Schenone、Paolo La Colla、Gabriella Collu、Giuseppina Sanna、Roberta Loddo

  DOI：10.1007/s00044-009-9192-x

  日期：2010.5

  The structural simplification of the non-nucleoside reverse transcriptase inhibitors (NNRTIs) O-(2-phthalimidoethyl)-N-(hetero)aroyl-N-arylthiocarbamates led us to design (hetero)aroyl esters of 2-(N-phthalimido)ethanol as a potential new class of anti-HIV-1 agents. The setup of a solution-phase parallel synthesis method allowed the rapid preparation of a high number of analogues. In cell-based assays, 20 of 34 esters showed anti-HIV-1 activity ranging from nanomolar to micromolar concentrations. The most potent esters had only a minor effect or were ineffective in enzyme assay against HIV-1 reverse transcriptase. Variations on the O-(2-phthalimidoethyl) moiety led to compounds devoid of antiretroviral activity, but cytotoxic, in particular those bearing the 4-chloro-3-nitrobenzoyl moiety. The most cytotoxic compound displayed a CC50 value of 1.6 mu M.