N-(3,4,5-trimethoxybenzyl)sulfamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(3,4,5-trimethoxybenzyl)sulfamide
• 英文别名: 1,2,3-Trimethoxy-5-[(sulfamoylamino)methyl]benzene；1,2,3-trimethoxy-5-[(sulfamoylamino)methyl]benzene
• 化学式: C₁₀H₁₆N₂O₅S
• mdl: MFCD26144761
• 分子量: 276.313
• InChiKey: ABFRJWZQRLHMCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苄胺 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(3,4,5-trimethoxybenzyl)sulfamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitory properties of novel benzylsulfamides using molecular modeling and experimental studies

  摘要：

  In this study, a series of sulfamoyl carbamates and sulfamide derivatives were synthesized. Six commercially available benzyl amines and BnOH were reacted with chlorosulfonyl isocyanate (CSI) to give sulfamoyl carbamates. Pd-C catalyzed hydrogenolysis reactions of carbamates afforded sulfamides. The inhibition effects of novel benzylsulfamides on the carbonic anhydrase I, and II isoenzymes (CA I, and CA II) purified from fresh human blood red cells were determined by Sepharose-4B-L-Tyrosine-sulfanilamide affinity chromatography. In vitro studies were shown that all of novel synthesized benzylsulfamide analogs inhibited, concentration dependently, both hCA isoenzyme activities. The novel benzylsulfamide compounds investigated here exhibited nanomolar inhibition constants against the two isoenzymes. K-i values were in the range of 28.48 +/- 0.01-837.09 +/- 0.19 nM and 112.01 +/- 0.01-268.01 +/- 0.22 nM for hCAI and hCA II isoenzymes, respectively. Molecular modeling approaches were also applied for studied compounds. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.07.009

文献信息

• Carbonic anhydrase inhibitory properties of novel benzylsulfamides using molecular modeling and experimental studies
  作者：Süleyman Göksu、Ali Naderi、Yusuf Akbaba、Pınar Kalın、Akın Akıncıoğlu、İlhami Gülçin、Serdar Durdagi、Ramin Ekhteiari Salmas

  DOI：10.1016/j.bioorg.2014.07.009

  日期：2014.10

  In this study, a series of sulfamoyl carbamates and sulfamide derivatives were synthesized. Six commercially available benzyl amines and BnOH were reacted with chlorosulfonyl isocyanate (CSI) to give sulfamoyl carbamates. Pd-C catalyzed hydrogenolysis reactions of carbamates afforded sulfamides. The inhibition effects of novel benzylsulfamides on the carbonic anhydrase I, and II isoenzymes (CA I, and CA II) purified from fresh human blood red cells were determined by Sepharose-4B-L-Tyrosine-sulfanilamide affinity chromatography. In vitro studies were shown that all of novel synthesized benzylsulfamide analogs inhibited, concentration dependently, both hCA isoenzyme activities. The novel benzylsulfamide compounds investigated here exhibited nanomolar inhibition constants against the two isoenzymes. K-i values were in the range of 28.48 +/- 0.01-837.09 +/- 0.19 nM and 112.01 +/- 0.01-268.01 +/- 0.22 nM for hCAI and hCA II isoenzymes, respectively. Molecular modeling approaches were also applied for studied compounds. (C) 2014 Elsevier Inc. All rights reserved.