(9H-fluoren-9-yl)methyl (3-oxo-3-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)propyl)carbamate | 1355987-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl (3-oxo-3-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)propyl)carbamate
• CAS: 1355987-21-1
• 化学式: C₂₀H₁₉N₅O₅S₂
• 分子量: 473.533
• InChiKey: URPVTTXIAYRRHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  153.37
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (3-oxo-3-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)propyl)carbamate 在 N-甲基吗啉 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 3-(2-((1E,3Z,5E)-5-(1,1-dimethyl-6,8-disulfo-3-(3-sulfopropyl)-1H-benzo[e]indol-2(3H)-ylidene)-3-(5-((3-oxo-3-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)propyl)carbamoyl)pyridin-2-yl)penta-1,3-dien-1-yl)-1,1-dimethyl-6,8-disulfo-1H-benzo[e]indol-3-ium-3-yl)propane-1-sulfonate
  参考文献：
  名称：

  [EN] CARBONIC ANHYDRASE TARGETING AGENTS AND METHODS OF USING SAME
  [FR] AGENTS DE CIBLAGE DE L'ANHYDRASE CARBONIQUE ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2012154885A3
• 作为产物：
  描述：

  5-氨基-1,3,4-噻二唑-2-磺酰胺 、 FMOC-beta-丙氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (9H-fluoren-9-yl)methyl (3-oxo-3-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)propyl)carbamate
  参考文献：
  名称：

  Synthesis and evaluation of near-infrared fluorescent sulfonamide derivatives for imaging of hypoxia-induced carbonic anhydrase IX expression in tumors

  摘要：

  A series of human carbonic anhydrase (hCA) IX inhibitors conjugated to various near-infrared fluorescent dyes was synthesized with the aim of imaging hypoxia-induced hCA IX expression in tumor cells in vitro, ex vivo and in vivo. The resulting compounds were profiled for inhibition of transmembrane hCA IX showing a range of potencies from 7.5 to 116 nM and up to 50-fold selectivity over the cytosolic form hCA II. Some of the compounds also showed inhibition selectivity for other transmembrane forms hCA XII and XIV as well. Compounds incubated in vitro with HeLa cells cultured under normoxic and hypoxic conditions detected upregulation of hCA IX under hypoxia by fluorescence microscopy. A pilot in vivo study in HT-29 tumor bearing mice showed significant accumulation of a fluorescent acetazolamide derivative in tumor tissue with little accumulation in other tissues. Approximately 10% of injected dose was non-invasively quantified in tumors by fluorescence molecular tomography (FMT), demonstrating the promise of these new compounds for quantitative imaging of hCA IX upregulation in live animals. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.058