N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-N-(4-fluoro-phenyl)-benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-N-(4-fluoro-phenyl)-benzenesulfonamide
• 英文别名: N-(3-carbazol-9-yl-2-hydroxypropyl)-N-(4-fluorophenyl)benzenesulfonamide
• 化学式: C₂₇H₂₃FN₂O₃S
• 分子量: 474.556
• InChiKey: MGGSPNAPOBJNCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-(环氧-2-甲基)-9H-咔唑 在 4-二甲氨基吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-N-(4-fluoro-phenyl)-benzenesulfonamide
  参考文献：
  名称：

  Sulfonamido-derivatives of unsubstituted carbazoles as BACE1 inhibitors

  摘要：

  A novel series of variously substituted N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-arylsulfonamides has been synthesized and assayed for beta-Secretase (BACE1) inhibitory activity. BACE1 is a widely recognized drug target for the prevention and treatment of Alzheimer's Disease (AD). The introduction of benzyl sub-stituents on the nitrogen atom of the arylsulfonamide moiety has so far led to the best results, with three derivatives showing IC50 values ranging from 1.6 to 1.9 mu M. Therefore, a significant improvement over the previously reported series of N-carboxamides (displaying IC50's >= 2.5 mu M) has been achieved, thus suggesting an active role of the sulfonamido-portion in the inhibition process. Preliminary molecular modeling studies have been carried out to rationalize the observed structure-activity relationships. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.058

文献信息

• Sulfonamido-derivatives of unsubstituted carbazoles as BACE1 inhibitors
  作者：Simone Bertini、Elisa Ghilardi、Valentina Asso、Filippo Minutolo、Simona Rapposelli、Maria Digiacomo、Giuseppe Saccomanni、Veronica Salmaso、Mattia Sturlese、Stefano Moro、Marco Macchia、Clementina Manera

  DOI：10.1016/j.bmcl.2017.09.058

  日期：2017.11

  A novel series of variously substituted N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-arylsulfonamides has been synthesized and assayed for beta-Secretase (BACE1) inhibitory activity. BACE1 is a widely recognized drug target for the prevention and treatment of Alzheimer's Disease (AD). The introduction of benzyl sub-stituents on the nitrogen atom of the arylsulfonamide moiety has so far led to the best results, with three derivatives showing IC50 values ranging from 1.6 to 1.9 mu M. Therefore, a significant improvement over the previously reported series of N-carboxamides (displaying IC50's >= 2.5 mu M) has been achieved, thus suggesting an active role of the sulfonamido-portion in the inhibition process. Preliminary molecular modeling studies have been carried out to rationalize the observed structure-activity relationships. (C) 2017 Elsevier Ltd. All rights reserved.