6-[(5Z)-5-[(2,5-dimethyl-1-phenylpyrrol-3-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 6-[(5Z)-5-[(2,5-dimethyl-1-phenylpyrrol-3-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
• 化学式: C₂₂H₂₄N₂O₃S₂
• 分子量: 428.576
• InChiKey: WELSZEIUODNEBT-RGEXLXHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[(5Z)-5-[(2,5-dimethyl-1-phenylpyrrol-3-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid 在 对甲苯磺酸 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-[(5Z)-5-[(2,5-dimethyl-1-phenylpyrrol-3-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-hydroxyhexanamide
  参考文献：
  名称：

  A Novel Class of Inhibitors of Peptide Deformylase Discovered through High-Throughput Screening and Virtual Ligand Screening

  摘要：

  Peptide deformylase (PDF) has been identified as a promising antibacterial and herbicide target. A structurally novel class of inhibitors containing a 2-thioxo-thiazolidin-4-one heterocycle substituted by an arylidene group at the 5-position and a hexanoic acid side chain at the 3-position was discovered independently via high-throughput screening and virtual ligand screening. Data mining and analogue synthesis established a structure-activity relationship for the side chain region that is consistent with the docked structure.

  DOI：

  10.1021/jm049222o
• 作为产物：
  描述：

  2,5-二甲基-1-苯基吡咯-3-羰醛 、 6-(4-氧代-2-三氧噻唑烷-3-基)-己酸 在 ethylenediamine Tetraacetic Acid 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以79%的产率得到6-[(5Z)-5-[(2,5-dimethyl-1-phenylpyrrol-3-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
  参考文献：
  名称：

  A Novel Class of Inhibitors of Peptide Deformylase Discovered through High-Throughput Screening and Virtual Ligand Screening

  摘要：

  Peptide deformylase (PDF) has been identified as a promising antibacterial and herbicide target. A structurally novel class of inhibitors containing a 2-thioxo-thiazolidin-4-one heterocycle substituted by an arylidene group at the 5-position and a hexanoic acid side chain at the 3-position was discovered independently via high-throughput screening and virtual ligand screening. Data mining and analogue synthesis established a structure-activity relationship for the side chain region that is consistent with the docked structure.

  DOI：

  10.1021/jm049222o

文献信息

• A Novel Class of Inhibitors of Peptide Deformylase Discovered through High-Throughput Screening and Virtual Ligand Screening
  作者：Michael H. Howard、Teodorica Cenizal、Steven Gutteridge、Wayne S. Hanna、Yong Tao、Maxim Totrov、Vernon A. Wittenbach、Ya-jun Zheng

  DOI：10.1021/jm049222o

  日期：2004.12.1

  Peptide deformylase (PDF) has been identified as a promising antibacterial and herbicide target. A structurally novel class of inhibitors containing a 2-thioxo-thiazolidin-4-one heterocycle substituted by an arylidene group at the 5-position and a hexanoic acid side chain at the 3-position was discovered independently via high-throughput screening and virtual ligand screening. Data mining and analogue synthesis established a structure-activity relationship for the side chain region that is consistent with the docked structure.