1-(4-Methoxy-benzyl)-3-(1-oxo-3-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione | 222713-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(4-Methoxy-benzyl)-3-(1-oxo-3-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione
• 英文别名: 1-[(4-methoxyphenyl)methyl]-3-(3-oxo-1-phenylsulfanyl-1H-isoindol-2-yl)piperidine-2,6-dione
• CAS: 222713-09-9
• 化学式: C₂₇H₂₄N₂O₄S
• 分子量: 472.565
• InChiKey: MLMVPLVRCCJTPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-Methoxy-benzyl)-3-(1-oxo-3-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione 在 镍 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以98%的产率得到1-(4-methoxybenzyl)-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione
  参考文献：
  名称：

  邻苯二甲酰亚胺⇌邻苯二甲酰亚胺转化的简便方案

  摘要：

  使用超声促进的阮内镍方案对苯硫内酰胺进行脱硫，得到相应的N-取代的邻苯二甲酰亚胺。所述的苄基氧化Ñ取代phthalimidines通过用2，2'-联吡啶酸（BPCC / MCPBA），得到原始邻苯二甲酰亚胺。还原脱硫用于制备作为TNF-α抑制剂的脱氧沙利度胺衍生物。

  DOI：

  10.1016/s0040-4039(99)00152-5
• 作为产物：
  描述：

  2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(4-methoxy-benzylcarbamoyl)-butyric acid 在 aluminium amalgam 、 水 、 乙酸酐 、 对甲苯磺酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 1-(4-Methoxy-benzyl)-3-(1-oxo-3-phenylsulfanyl-1,3-dihydro-isoindol-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

文献信息

• A facile scheme for phthalimide ⇌ phthalimidine conversion
  作者：Frederick A. Luzzio、DeAnna Piatt Zacherl、William D. Figg

  DOI：10.1016/s0040-4039(99)00152-5

  日期：1999.3

  Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2, 2′-bipyridinium acid (BPCC/MCPBA) affords the original phthalimides. Thereduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor

  使用超声促进的阮内镍方案对苯硫内酰胺进行脱硫，得到相应的N-取代的邻苯二甲酰亚胺。所述的苄基氧化Ñ取代phthalimidines通过用2，2'-联吡啶酸（BPCC / MCPBA），得到原始邻苯二甲酰亚胺。还原脱硫用于制备作为TNF-α抑制剂的脱氧沙利度胺衍生物。
• 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.