N-((2S,3S)-3-hydroxy-1-phenyl-4-(pyridin-2-ylthio)butan-2-yl)-4-methylbenzenesulfonamide | 1345822-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((2S,3S)-3-hydroxy-1-phenyl-4-(pyridin-2-ylthio)butan-2-yl)-4-methylbenzenesulfonamide
• 英文别名: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-pyridylsulfanyl)propyl]-4-methyl-benzenesulfonamide；N-[(2S,3S)-3-hydroxy-1-phenyl-4-pyridin-2-ylsulfanylbutan-2-yl]-4-methylbenzenesulfonamide
• CAS: 1345822-08-3
• 化学式: C₂₂H₂₄N₂O₃S₂
• 分子量: 428.576
• InChiKey: JBJMOYHEDUGNJV-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 N-((2S,3S)-3-hydroxy-1-phenyl-4-(pyridin-2-ylthio)butan-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Antibacterial Activity of Thioetherhydroxyethylsulfonamide Derivatives

  摘要：

  合成了噻噁唑羟乙基磺酰胺衍生物，并评估其对大肠杆菌（ATCC 25922）、铜绿假单胞菌（ATCC 27853）和金黄色葡萄球菌（ATCC 25923）的体外抗菌活性。结果显示，化合物8c和9e对大肠杆菌的活性强劲（MIC = 0.125 µg/mL），相比之下，标准药物磺胺甲恶唑（SMZ，MIC < 0.5 µg/mL）对该菌株的效果也相当。所有新化合物均通过NMR（1H和13C）和X射线晶体学（针对化合物8c）进行了全面的鉴定和表征。这类化合物可以被视为在抗击多重耐药细菌方面开发新靶分子的良好起点。

  DOI：

  10.2174/1573406410666140218103022

文献信息

• Synthesis and antimalarial activity of thioetherhydroxyethylsulfonamides, potential aspartyl protease inhibitors, Part 3
  作者：Walcimar T. Vellasco Junior、Guilherme P. Guedes、Thatyana R.A. Vasconcelos、Maria G.F. Vaz、Marcus V.N. de Souza、Antoniana U. Krettli、Luisa G. Krettli、Anna Caroline C. Aguiar、Claudia R.B. Gomes、Wilson Cunico

  DOI：10.1016/j.ejmech.2011.09.025

  日期：2011.11

  A series of novel thioetherhydroxyethylsulfonamide derivatives has been synthesized from the coupling of intermediates 3-amino-4-phenyl-1-thioetherazine-butan-2-oles 6,7 with arenesulfonyl chlorides in good yields. Characterizations of products were achieved by NMR techniques and specifically for compound 8e by X-ray crystallography. Preliminary results of antimalarial activity in vitro against the Plasmodium falciparum W2 clone (chloroquine resistant and mefloquine sensitive) showed moderate activity for hydroxyethylsulfonamide 8f. In addition, none of the compounds tested showed cytotoxicity at high concentration tested against HepG2 and BGM cell lines. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Antibacterial Activity of Thioetherhydroxyethylsulfonamide Derivatives
  作者：Walcimar Vellasco Junior、Guilherme Guedes、Victor Facchinetti、Thatyana Vasconcelos、Maria Vaz、Wilson Cunico、Marcus de Souza、Geraldo de Paula、Maria Fleming、Claudia Gomes

  DOI：10.2174/1573406410666140218103022

  日期：2014.3.31

  Thioetherhydroxyethylsulfonamide derivatives were synthesized and evaluated for their in vitro antibacterial activity against Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (ATCC 25923). Results have shown that compounds 8c and 9e display potent activity (MIC = 0.125 µg/mL) against E. coli when compared with the standard drug sulfamethoxazole (SMZ, MIC < 0.5 µg/mL) for this same strain. All the new compounds were fully identified and characterized by NMR (1H and 13C) and X-ray crystallography (for compound 8c). This class of compounds can be considered as a good starting point for the development of new lead molecules in the fight against multi-drug bacterial resistance.

  合成了噻噁唑羟乙基磺酰胺衍生物，并评估其对大肠杆菌（ATCC 25922）、铜绿假单胞菌（ATCC 27853）和金黄色葡萄球菌（ATCC 25923）的体外抗菌活性。结果显示，化合物8c和9e对大肠杆菌的活性强劲（MIC = 0.125 µg/mL），相比之下，标准药物磺胺甲恶唑（SMZ，MIC < 0.5 µg/mL）对该菌株的效果也相当。所有新化合物均通过NMR（1H和13C）和X射线晶体学（针对化合物8c）进行了全面的鉴定和表征。这类化合物可以被视为在抗击多重耐药细菌方面开发新靶分子的良好起点。