2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(4-methoxy-benzylcarbamoyl)-butyric acid | 912893-81-3

• 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: 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(4-methoxy-benzylcarbamoyl)-butyric acid
• 英文别名: 2-(1,3-Dioxoisoindol-2-yl)-5-[(4-methoxyphenyl)methylamino]-5-oxopentanoic acid
• CAS: 912893-81-3
• 化学式: C₂₁H₂₀N₂O₆
• 分子量: 396.4
• InChiKey: FFMYUESVMAIZOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(4-methoxy-benzylcarbamoyl)-butyric acid 在 镍 aluminium amalgam 、 水 、 乙酸酐 、 对甲苯磺酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 1-(4-methoxybenzyl)-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione
  参考文献：
  名称：

  Thalidomide Metabolites and Analogues. 3. Synthesis and Antiangiogenic Activity of the Teratogenic and TNFα-Modulatory Thalidomide Analogue 2-(2,6-Dioxopiperidine-3-yl)phthalimidine

  摘要：

  Versatile synthesis of the teratogenic, TNFalpha-modulatory, and antiangiogenic thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine (1) and its direct antiangiogenic properties are described. With thalidomide or thalidomide derivatives as precursors, the synthesis involved either carbonyl reduction/thiation-desulfurization or carbonyl reduction/acyliminium ion reduction protocols. Compared to earlier studies with thalidomide, which was only active with microsomal treatment, I exhibited marginal inhibitory activity in the rat aortic ring assay, thereby demonstrating the requirement for metabolic activation.

  DOI：

  10.1021/jm020079d
• 作为产物：
  描述：

  (L)-2-苯二甲酰亚氨基戊二酸 在 吡啶 、 乙酸酐 、 三氟乙酸酐 作用下， 反应 25.5h， 生成 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(4-methoxy-benzylcarbamoyl)-butyric acid
  参考文献：
  名称：

  Thalidomide Metabolites and Analogues. 3. Synthesis and Antiangiogenic Activity of the Teratogenic and TNFα-Modulatory Thalidomide Analogue 2-(2,6-Dioxopiperidine-3-yl)phthalimidine

  摘要：

  Versatile synthesis of the teratogenic, TNFalpha-modulatory, and antiangiogenic thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine (1) and its direct antiangiogenic properties are described. With thalidomide or thalidomide derivatives as precursors, the synthesis involved either carbonyl reduction/thiation-desulfurization or carbonyl reduction/acyliminium ion reduction protocols. Compared to earlier studies with thalidomide, which was only active with microsomal treatment, I exhibited marginal inhibitory activity in the rat aortic ring assay, thereby demonstrating the requirement for metabolic activation.

  DOI：

  10.1021/jm020079d

文献信息

• Thalidomide Metabolites and Analogues. 3. Synthesis and Antiangiogenic Activity of the Teratogenic and TNFα-Modulatory Thalidomide Analogue 2-(2,6-Dioxopiperidine-3-yl)phthalimidine
  作者：Frederick A. Luzzio、Alexander V. Mayorov、Sylvia S. W. Ng、Erwin A. Kruger、William D. Figg

  DOI：10.1021/jm020079d

  日期：2003.8.1

  Versatile synthesis of the teratogenic, TNFalpha-modulatory, and antiangiogenic thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine (1) and its direct antiangiogenic properties are described. With thalidomide or thalidomide derivatives as precursors, the synthesis involved either carbonyl reduction/thiation-desulfurization or carbonyl reduction/acyliminium ion reduction protocols. Compared to earlier studies with thalidomide, which was only active with microsomal treatment, I exhibited marginal inhibitory activity in the rat aortic ring assay, thereby demonstrating the requirement for metabolic activation.