N-[4-(aminosulfonyl)benzyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiourea | 1370612-40-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[4-(aminosulfonyl)benzyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiourea
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(4-sulfamoylphenyl)methylcarbamothioylamino]oxan-2-yl]methyl acetate
• CAS: 1370612-40-0
• 化学式: C₂₂H₂₉N₃O₁₁S₂
• 分子量: 575.618
• InChiKey: CCJBAOGUTFGYCW-XDWAVFMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  239
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N-[4-(aminosulfonyl)benzyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiourea 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 N-[4-(aminosulfonyl)benzyl]-N'-(β-D-galactopyranosyl)thiourea
  参考文献：
  名称：

  Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases

  摘要：

  A library of 32 novel glycoconjugate thiourea-bridged benzene sulfonamides have been synthesized from the reaction of glycosyl isothiocyanates with a panel of simple benzene sulfonamides comprising either a free amine or hydrazide. All compounds were investigated for their ability to inhibit the enzymatic activity of five human carbonic anhydrase (hCA) isozymes: hCA I, II and membrane-associated isozymes IX, XII and XIV. A physicochemical feature of the free sugar thioureido glycoconjugates was high water solubility (>20 mg/mL), as well many of these compounds exhibited a desirable potency and CA isozyme selectivity profile. From this library several inhibitors displayed excellent potency-selectivity profiles for transmembrane anchored CAs over off-target CA I and II. These molecules provide potential dual-acting candidates for the development of inhibitors that target the extracellular CAs (IX, XII and XIV)-either directly as free sugars (membrane impermeable) or indirectly as acetylated prodrugs, becoming free sugars upon esterase hydrolysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.052
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 四氯化锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 N-[4-(aminosulfonyl)benzyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiourea
  参考文献：
  名称：

  Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases

  摘要：

  A library of 32 novel glycoconjugate thiourea-bridged benzene sulfonamides have been synthesized from the reaction of glycosyl isothiocyanates with a panel of simple benzene sulfonamides comprising either a free amine or hydrazide. All compounds were investigated for their ability to inhibit the enzymatic activity of five human carbonic anhydrase (hCA) isozymes: hCA I, II and membrane-associated isozymes IX, XII and XIV. A physicochemical feature of the free sugar thioureido glycoconjugates was high water solubility (>20 mg/mL), as well many of these compounds exhibited a desirable potency and CA isozyme selectivity profile. From this library several inhibitors displayed excellent potency-selectivity profiles for transmembrane anchored CAs over off-target CA I and II. These molecules provide potential dual-acting candidates for the development of inhibitors that target the extracellular CAs (IX, XII and XIV)-either directly as free sugars (membrane impermeable) or indirectly as acetylated prodrugs, becoming free sugars upon esterase hydrolysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.052

文献信息

• Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases
  作者：Janina Moeker、Kanae Teruya、Sabine Rossit、Brendan L. Wilkinson、Marie Lopez、Laurent F. Bornaghi、Alessio Innocenti、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1016/j.bmc.2012.01.052

  日期：2012.4

  A library of 32 novel glycoconjugate thiourea-bridged benzene sulfonamides have been synthesized from the reaction of glycosyl isothiocyanates with a panel of simple benzene sulfonamides comprising either a free amine or hydrazide. All compounds were investigated for their ability to inhibit the enzymatic activity of five human carbonic anhydrase (hCA) isozymes: hCA I, II and membrane-associated isozymes IX, XII and XIV. A physicochemical feature of the free sugar thioureido glycoconjugates was high water solubility (>20 mg/mL), as well many of these compounds exhibited a desirable potency and CA isozyme selectivity profile. From this library several inhibitors displayed excellent potency-selectivity profiles for transmembrane anchored CAs over off-target CA I and II. These molecules provide potential dual-acting candidates for the development of inhibitors that target the extracellular CAs (IX, XII and XIV)-either directly as free sugars (membrane impermeable) or indirectly as acetylated prodrugs, becoming free sugars upon esterase hydrolysis. (C) 2012 Elsevier Ltd. All rights reserved.