2-{(4R,5R)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-ylmethyl}isoindole-1,3-dione | 870279-43-9

• 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-{(4R,5R)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-ylmethyl}isoindole-1,3-dione
• 英文别名: 2-[[(4R,5R)-2,2-dimethyl-5-[tri(propan-2-yl)silyloxymethyl]-1,3-dioxolan-4-yl]methyl]isoindole-1,3-dione
• CAS: 870279-43-9
• 化学式: C₂₄H₃₇NO₅Si
• 分子量: 447.647
• InChiKey: FUFDGTSXXPGLQO-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{(4R,5R)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-ylmethyl}isoindole-1,3-dione 在 吡啶 、 四丁基氟化铵 、 sodium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 醋酸异丙酯 、 水 为溶剂， 反应 6.0h， 生成 tert-butyl {(4R,5R)-5-(bis-benzyloxy-phosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}carbamate
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase

  摘要：

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.

  DOI：

  10.1021/jo0516786
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 在 偶氮二甲酸二异丙酯 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-{(4R,5R)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-ylmethyl}isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase

  摘要：

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.

  DOI：

  10.1021/jo0516786

文献信息

• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase
  作者：Joel R. Walker、C. Dale Poulter

  DOI：10.1021/jo0516786

  日期：2005.11.1

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.