4-[2-(1-naphthalen-1-yl-ethyl)ureido]phenyl sulfamate | 1330061-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[2-(1-naphthalen-1-yl-ethyl)ureido]phenyl sulfamate
• 英文别名: 4-[3-(2-naphthalen-1-yl-ethyl)ureido]phenyl sulfamate；BO592；[4-(2-Naphthalen-1-ylethylcarbamoylamino)phenyl] sulfamate
• CAS: 1330061-96-5
• 化学式: C₁₉H₁₉N₃O₄S
• 分子量: 385.444
• InChiKey: DSHOYDPDINYHJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-hydroxyphenyl)-3-(2-(naphthalen-1-yl)ethyl)urea 在 氨基磺酰氯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 4-[2-(1-naphthalen-1-yl-ethyl)ureido]phenyl sulfamate
  参考文献：
  名称：

  Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines

  摘要：

  A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic offtarget isoforms CA I and II. Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.083

文献信息

• Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines
  作者：Jean-Yves Winum、Fabrizio Carta、Carol Ward、Peter Mullen、David Harrison、Simon P. Langdon、Alessandro Cecchi、Andrea Scozzafava、Ian Kunkler、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2012.05.083

  日期：2012.7

  A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic offtarget isoforms CA I and II. Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads. (C) 2012 Elsevier Ltd. All rights reserved.