tert-butyl N-[[4-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)carbamoyl]phenyl]methyl]carbamate | 1355987-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl N-[[4-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)carbamoyl]phenyl]methyl]carbamate
• CAS: 1355987-16-4
• 化学式: C₁₅H₁₉N₅O₅S₂
• 分子量: 413.478
• InChiKey: UGSROZIKHVYGMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  190
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[[4-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)carbamoyl]phenyl]methyl]carbamate 在 N-甲基吗啉 、 水 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 3-(2-((1E,3E,5E)-5-(1,1-dimethyl-6,8-disulfo-3-(3-sulfopropyl)-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dien-1-yl)-1,1-dimethyl-6-(N-methyl-N-(4-oxo-4-((4-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)carbamoyl)benzyl)amino)butyl)sulfamoyl)-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 、 4-[(叔丁氧羰基氨基)甲基]苯甲酸 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 tert-butyl N-[[4-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)carbamoyl]phenyl]methyl]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

文献信息

• Carbonic Anhydrase Targeting Agents and Methods of Using Same
  申请人：Groves Kevin

  公开号：US20120321563A1

  公开（公告）日：2012-12-20

  The invention provides agents that target carbonic anhydrase, which can be used as imaging agents or therapeutic agents. The agents can be used to image tumor hypoxia as well as other physiological processes in a subject.

  该发明提供了针对碳酸酐酶的药剂，可用作成像药剂或治疗药剂。这些药剂可用于成像肿瘤缺氧以及主体其他的生理过程。
• Carbonic anhydrase targeting agents and methods of using same
  申请人：Groves Kevin

  公开号：US10221159B2

  公开（公告）日：2019-03-05

  The invention provides agents that target carbonic anhydrase, which can be used as imaging agents or therapeutic agents. The agents can be used to image tumor hypoxia as well as other physiological processes in a subject.

  本发明提供靶向碳酸酐酶的制剂，可用作成像剂或治疗剂。这些制剂可用于成像肿瘤缺氧以及受试者的其他生理过程。
• CARBONIC ANHYDRASE TARGETING AGENTS AND METHODS OF USING SAME
  申请人：VisEn Medical, Inc.

  公开号：US20190300501A1

  公开（公告）日：2019-10-03

  The invention provides agents that target carbonic anhydrase, which can be used as imaging agents or therapeutic agents. The agents can be used to image tumor hypoxia as well as other physiological processes in a subject.
• Synthesis and evaluation of near-infrared fluorescent sulfonamide derivatives for imaging of hypoxia-induced carbonic anhydrase IX expression in tumors
  作者：Kevin Groves、Bagna Bao、Jun Zhang、Emma Handy、Paul Kennedy、Garry Cuneo、Claudiu T. Supuran、Wael Yared、Jeffrey D. Peterson、Milind Rajopadhye

  DOI：10.1016/j.bmcl.2011.10.058

  日期：2012.1

  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.
• [EN] CARBONIC ANHYDRASE TARGETING AGENTS AND METHODS OF USING SAME<br/>[FR] AGENTS DE CIBLAGE DE L'ANHYDRASE CARBONIQUE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：VISEN MEDICAL INC

  公开号：WO2012154885A3

  公开（公告）日：2013-04-04