chroman-2-ylmethylsulfamate | 835894-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: chroman-2-ylmethylsulfamate
• 英文别名: Sulfamic acid chroman-2-ylmethyl ester；3,4-dihydro-2H-chromen-2-ylmethyl sulfamate
• CAS: 835894-63-8
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: OXNGFJDSVRPPCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯并二氢吡喃-2-羧酸 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 chroman-2-ylmethylsulfamate
  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

• [EN] SULFAMATE AND SULFAMIDE DERIVATIVES FOR THE TREATMENT OF EPILEPSY AND RELATED DISORDERS<br/>[FR] DÉRIVÉS DE SULFAMATE ET DE SULFAMIDE POUR LE TRAITEMENT DE L'ÉPILEPSIE ET DE TROUBLES APPARENTÉS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006007435A1

  公开（公告）日：2006-01-19

  The present invention is directed to novel sulfamide and sulfamate derivatives, pharmaceutical composlons containing them and their use in the treatment of epilepsy and related disorders.

  本发明涉及新型磺胺酰胺和磺酸酯衍生物，包含它们的药物组合物以及它们在治疗癫痫和相关疾病中的用途。
• Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders
  申请人：McComsey F. David

  公开号：US20050282887A1

  公开（公告）日：2005-12-22

  The present invention is directed to novel sulfamide and sulfamate derivatives, pharmaceutical compositions containing them and their use in the treatment of epilepsy and related disorders.

  本发明涉及新型磺胺酰胺和磺酸酯衍生物，包括含有它们的药物组合物以及它们在治疗癫痫和相关疾病中的用途。
• SULFAMATE AND SULFAMIDE DERIVATIVES FOR THE TREATMENT OF EPILEPSY AND RELATED DISORDERS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1768970A1

  公开（公告）日：2007-04-04
• US8084490B2
  申请人：——

  公开号：US8084490B2

  公开（公告）日：2011-12-27
• 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.