4-oxo-2-thioxo-3-thiazolidineoctanoic acid | 833482-73-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-oxo-2-thioxo-3-thiazolidineoctanoic acid
• 英文别名: 3-Thiazolidineoctanoic acid, 4-oxo-2-thioxo-；8-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)octanoic acid
• CAS: 833482-73-8
• 化学式: C₁₁H₁₇NO₃S₂
• 分子量: 275.393
• InChiKey: SLFXFLFQXGJRMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-二甲基-1-苯基吡咯-3-羰醛 、 4-oxo-2-thioxo-3-thiazolidineoctanoic acid 在 ethylenediamine Tetraacetic Acid 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以38%的产率得到8-[(5Z)-5-[(2,5-dimethyl-1-phenylpyrrol-3-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]octanoic 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
• 作为产物：
  描述：

  二硫化碳 、 8-氨基辛酸 、 氯乙酸 在 氢氧化钾 、 硫酸 作用下， 以29%的产率得到4-oxo-2-thioxo-3-thiazolidineoctanoic 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.