(2E)-3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)-N-(2-sulfamoylethyl)propanamide | 133991-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2E)-3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)-N-(2-sulfamoylethyl)propanamide
• 英文别名: psammaplin C；(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyimino-N-(2-sulfamoylethyl)propanamide
• CAS: 133991-68-1
• 化学式: C₁₁H₁₄BrN₃O₅S
• 分子量: 380.219
• InChiKey: LZIKVOPNIDEBQJ-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (Z)-5-(4-(benzyloxy)-3,5-dibromobenzylidene)-2-thioxothiazolidin-4-one 在 碘代三甲硅烷 、 sodium ethanolate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (2E)-3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)-N-(2-sulfamoylethyl)propanamide
  参考文献：
  名称：

  Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines

  摘要：

  The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.

  DOI：

  10.1021/ol303057a

文献信息

• An Unusual Natural Product Primary Sulfonamide: Synthesis, Carbonic Anhydrase Inhibition, and Protein X-ray Structures of Psammaplin C
  作者：Prashant Mujumdar、Kanae Teruya、Kathryn F. Tonissen、Daniela Vullo、Claudiu T. Supuran、Thomas S. Peat、Sally-Ann Poulsen

  DOI：10.1021/acs.jmedchem.6b00443

  日期：2016.6.9

  the synthesis of psammaplin C and evaluate the inhibition profile against therapeutically relevant carbonic anhydrase (CA) zinc metalloenzymes. The compound exhibited unprecedented inhibition of an important cancer-associated isozyme, hCA XII, with a Ki of 0.79 nM. The compound also displayed good isoform selectivity for hCA XII over other CAs. We present the first reported protein X-ray crystal structures

  帕马普林C是仅两种描述的天然产物伯磺酰胺之一。在这里，我们报告了psammaplin C的合成，并评估了对治疗相关的碳酸酐酶（CA）锌金属酶的抑制作用。该化合物对一种重要的癌症相关同工酶hCA XII的K i抑制作用史无前例。为0.79 nM。该化合物还显示出对hCA XII优于其他CA的良好同工型选择性。我们目前首次报道了与人类CA复杂的psammaplin C的蛋白质X射线晶体结构。我们设计了易于结晶的hCA II酶以模拟hCA IX和hCA XII结合位点，然后利用蛋白质X射线晶体学确定psammaplin C在hCA II，hCA IX和hCA XII模拟活性位点内的结合姿势，全部到高分辨率。这是首次评估天然产物伯磺酰胺抑制剂的抑制作用以及与CA的结合。
• Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines
  作者：Suresh K. Kottakota、Mathew Benton、Dimitrios Evangelopoulos、Juan D. Guzman、Sanjib Bhakta、Timothy D. McHugh、Mark Gray、Paul W. Groundwater、Emma C. L. Marrs、John D. Perry、J. Jonathan Harburn

  DOI：10.1021/ol303057a

  日期：2012.12.21

  The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.