2-(1,2-benzothiazol-3-ylamino)-5-[(4-nitrophenyl)methylidene]-1,3-thiazol-4-one | 1027341-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(1,2-benzothiazol-3-ylamino)-5-[(4-nitrophenyl)methylidene]-1,3-thiazol-4-one
• CAS: 1027341-22-5
• 化学式: C₁₇H₁₀N₄O₃S₂
• 分子量: 382.423
• InChiKey: PLFJMTKUJWPCGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.49
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-氨基-1,2-苯并异噻唑 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1,2-benzothiazol-3-ylamino)-5-[(4-nitrophenyl)methylidene]-1,3-thiazol-4-one
  参考文献：
  名称：

  Heteroarylimino-4-thiazolidinones as inhibitors of cartilage degradation

  摘要：

  2-Benzo[d]thiazolyl- and 2-benzo[d]isothiazolyl-imino-5-benzylidene-4-thiazolidinone derivatives were investigated as potential metalloproteinases (MMPs) inhibitors and evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1 beta, using an experimental model that reproduces the mechanisms involved in osteoarthritic (OA) diseases. Cell viability, the amount of glycosaminoglycans (GAGs) and the production of nitric oxide (NO) were measured. The most potent compound, 5-(4-methoxy-benzylidene)-2-(benzo[d]isothiazol-3-ylimino)-thiazolidin-4-one (4b), a MMP-13 inhibitor at nanomolar concentration (IC50 = 0.036 mu M), could be considered as a lead compound for the development of novel clinical agents, inhibitors of cartilage degradation, for the treatment of OA. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.11.002

文献信息

• Heteroarylimino-4-thiazolidinones as inhibitors of cartilage degradation
  作者：Anna Maria Panico、Paola Vicini、Athina Geronikaki、Matteo Incerti、Venera Cardile、Lucia Crascì、Rossella Messina、Simone Ronsisvalle

  DOI：10.1016/j.bioorg.2010.11.002

  日期：2011.2

  2-Benzo[d]thiazolyl- and 2-benzo[d]isothiazolyl-imino-5-benzylidene-4-thiazolidinone derivatives were investigated as potential metalloproteinases (MMPs) inhibitors and evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1 beta, using an experimental model that reproduces the mechanisms involved in osteoarthritic (OA) diseases. Cell viability, the amount of glycosaminoglycans (GAGs) and the production of nitric oxide (NO) were measured. The most potent compound, 5-(4-methoxy-benzylidene)-2-(benzo[d]isothiazol-3-ylimino)-thiazolidin-4-one (4b), a MMP-13 inhibitor at nanomolar concentration (IC50 = 0.036 mu M), could be considered as a lead compound for the development of novel clinical agents, inhibitors of cartilage degradation, for the treatment of OA. (C) 2010 Elsevier Inc. All rights reserved.