4-[(2H-1,3-Benzodioxol-5-yl)methyl]-1,2,4-triazolidine-3,5-dione | 682336-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-[(2H-1,3-Benzodioxol-5-yl)methyl]-1,2,4-triazolidine-3,5-dione
• 英文别名: 4-(1,3-benzodioxol-5-ylmethyl)-1,2,4-triazolidine-3,5-dione
• CAS: 682336-51-2
• 化学式: C₁₀H₉N₃O₄
• 分子量: 235.199
• InChiKey: YVGWZQKZILQCQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(2H-1,3-Benzodioxol-5-yl)methyl]-1,2,4-triazolidine-3,5-dione 在 palladium on activated charcoal sodium hydroxide 、 叠氮基三甲基硅烷 、 氢气 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 1-O'-tert-butyl 8-O-methyl 2-(1,3-benzodioxol-5-ylmethyl)-1,3-dioxospiro[7,8-dihydro-6H-[1,2,4]triazolo[1,2-a]pyridazine-5,4'-piperidine]-1',8-dicarboxylate
  参考文献：
  名称：

  Discovery of a Potent and Novel Motilin Agonist

  摘要：

  A novel series of dihydro- and tetrahydrotriazolopyridazine-1,3-dione-based amino acid derivatives were identified as very potent motilin receptor agonists. Incorporating one additional phenylethyl glycinamide subunit to 1 (EC50 = 660 nM) was found to improve in vitro potency approximately 3000-fold, resulting in compound 10 (EC50 = 0.22 nM). The more potent enantiomer 11A has an EC50 of 0.047 nM in the motilin receptor functional assay and a K-i of 0.7 nM in the binding assay. In addition, compound 11A was shown to have a significantly reduced tendency to cause receptor desensitization as compared with the motilin receptor agonist ABT-229.

  DOI：

  10.1021/jm0304865
• 作为产物：
  描述：

  methyl N-(1,3-benzodioxol-5-ylmethylcarbamoylamino)carbamate 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 3.0h， 以58%的产率得到4-[(2H-1,3-Benzodioxol-5-yl)methyl]-1,2,4-triazolidine-3,5-dione
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL AS MOTILIN AGONISTS AND METHOD
  [FR] COMPOSES UTILES EN TANT QU'AGONISTES DE LA MOTILINE ET PROCEDE

  摘要：

  提供了一些化合物，用于治疗胃肠道运动障碍，其结构为[在此插入化学结构]或其药用可接受的盐，其前药酯，以及所有立体异构体，其中R1和R2相同或不同，并且独立地选择自氢，烷基，芳基，环烷基，烯基，炔基，芳基烷基，杂环芳基，杂环芳基烷基或杂环烷基；Z从-CON（R4）R4a，-CO2R4，-SO2N（R4）R4a，-SO2R4，CN和[化学结构]中选择，[化学结构]，[化学结构]，[化学结构]或[化学结构]；R4和R4a相同或不同，并且独立地选择自氢，烷基，环烷基，芳基，芳基烷基，杂环芳基或杂环芳基烷基，或者R4和R4a可以结合在一起形成一个杂环。R4b从氢，卤素，羟基，CN，OCF3，CF3，CONH2，SONH2，SO2CH3，NHCOCH3或NHCO2CH3中选择；Q是一个取代的双环杂环。还提供了一种使用这些化合物治疗胃肠道运动障碍的方法。

  公开号：

  WO2005027637A1

文献信息

• Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds
  作者：Xiaoguang Lei、Nava Zaarur、Michael Y. Sherman、John A. Porco

  DOI：10.1021/jo050956y

  日期：2005.8.1

  We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.