Trifluoro-methanesulfonic acid (3aR,5aS,8aS,8bS)-7,7-dimethyl-2,2-dioxo-tetrahydro-2λ⁶-[1,3,2]dioxathiolo[4,5-d][1,3]dioxalo[4,5-b]pyran-5a-ylmethyl ester | 835894-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Trifluoro-methanesulfonic acid (3aR,5aS,8aS,8bS)-7,7-dimethyl-2,2-dioxo-tetrahydro-2λ⁶-[1,3,2]dioxathiolo[4,5-d][1,3]dioxalo[4,5-b]pyran-5a-ylmethyl ester
• 英文别名: [(1S,2S,6R,9S)-11,11-dimethyl-4,4-dioxo-3,5,8,10,12-pentaoxa-4lambda6-thiatricyclo[7.3.0.02,6]dodecan-9-yl]methyl trifluoromethanesulfonate；[(1S,2S,6R,9S)-11,11-dimethyl-4,4-dioxo-3,5,8,10,12-pentaoxa-4λ6-thiatricyclo[7.3.0.02,6]dodecan-9-yl]methyl trifluoromethanesulfonate
• CAS: 835894-57-0
• 化学式: C₁₀H₁₃F₃O₁₀S₂
• 分子量: 414.334
• InChiKey: ZSSZUVLJWOGCJQ-JAKMQLQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3aR,5aS,8aS,8bS)-7,7-dimethyl-2,2-dioxo-tetrahydro-2λ⁶-[1,3,2]dioxathiolo[4,5-d][1,3]dioxalo[4,5-b]pyran-5a-ylmethyl ester 在 palladium on activated charcoal sodium azide 、 氢气 、 磺酰胺 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 23.0 ℃ 、289.58 kPa 条件下， 反应 48.5h， 生成 (1S,2S,6R,9S)-11,11-dimethyl-4,4-dioxo-9-[(sulfamoylamino)methyl]-3,5,8,10,12-pentaoxa-4lambda6-thiatricyclo[7.3.0.02,6]dodecane
  参考文献：
  名称：

  Comparison of Sulfamate and Sulfamide Groups for the Inhibition of Carbonic Anhydrase-II by Using Topiramate as a Structural Platform

  摘要：

  This paper examines the relative effectiveness of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II (CA-H). Topiramate (1) and its sulfamide analogue 4, and 4,5-cyclic sulfate 6 and its sulfamide analogue 5, were compared for inhibition of human CA-II. A colorimetric assay, based on the pH shift that accompanies hydration of carbon dioxide, and an esterase assay were used. For these bioisosteric pairs, 1/4 and 6/5, the sulfamate compound was markedly more potent than its sulfamide counterpart. A similar, large difference in potency was also observed for the sulfamate/sulfamide pairs 14/15 and 16/17. These results indicate that the sulfamide moiety is not particularly suitable for obtaining potent carbonic anhydrase inhibition. A discussion of this structure-activity relationship with respect to the interactions of 1 and 6 with CA-H from published X-ray data is presented. A metabolic acidosis study was performed in rats with 1, 4, 6, and 2, and the results are discussed with respect to the degree of inhibition of CA-II in vivo.

  DOI：

  10.1021/jm040124c
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2,3-O-(isopropylidene)-4,5-O-sulfonyl-β-D-fructopyranose 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到Trifluoro-methanesulfonic acid (3aR,5aS,8aS,8bS)-7,7-dimethyl-2,2-dioxo-tetrahydro-2λ⁶-[1,3,2]dioxathiolo[4,5-d][1,3]dioxalo[4,5-b]pyran-5a-ylmethyl ester
  参考文献：
  名称：

  Comparison of Sulfamate and Sulfamide Groups for the Inhibition of Carbonic Anhydrase-II by Using Topiramate as a Structural Platform

  摘要：

  This paper examines the relative effectiveness of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II (CA-H). Topiramate (1) and its sulfamide analogue 4, and 4,5-cyclic sulfate 6 and its sulfamide analogue 5, were compared for inhibition of human CA-II. A colorimetric assay, based on the pH shift that accompanies hydration of carbon dioxide, and an esterase assay were used. For these bioisosteric pairs, 1/4 and 6/5, the sulfamate compound was markedly more potent than its sulfamide counterpart. A similar, large difference in potency was also observed for the sulfamate/sulfamide pairs 14/15 and 16/17. These results indicate that the sulfamide moiety is not particularly suitable for obtaining potent carbonic anhydrase inhibition. A discussion of this structure-activity relationship with respect to the interactions of 1 and 6 with CA-H from published X-ray data is presented. A metabolic acidosis study was performed in rats with 1, 4, 6, and 2, and the results are discussed with respect to the degree of inhibition of CA-II in vivo.

  DOI：

  10.1021/jm040124c

文献信息

• Comparison of Sulfamate and Sulfamide Groups for the Inhibition of Carbonic Anhydrase-II by Using Topiramate as a Structural Platform
  作者：Bruce E. Maryanoff、David F. McComsey、Michael J. Costanzo、Coralie Hochman、Virginia Smith-Swintosky、Richard P. Shank

  DOI：10.1021/jm040124c

  日期：2005.3.1

  This paper examines the relative effectiveness of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II (CA-H). Topiramate (1) and its sulfamide analogue 4, and 4,5-cyclic sulfate 6 and its sulfamide analogue 5, were compared for inhibition of human CA-II. A colorimetric assay, based on the pH shift that accompanies hydration of carbon dioxide, and an esterase assay were used. For these bioisosteric pairs, 1/4 and 6/5, the sulfamate compound was markedly more potent than its sulfamide counterpart. A similar, large difference in potency was also observed for the sulfamate/sulfamide pairs 14/15 and 16/17. These results indicate that the sulfamide moiety is not particularly suitable for obtaining potent carbonic anhydrase inhibition. A discussion of this structure-activity relationship with respect to the interactions of 1 and 6 with CA-H from published X-ray data is presented. A metabolic acidosis study was performed in rats with 1, 4, 6, and 2, and the results are discussed with respect to the degree of inhibition of CA-II in vivo.