(E)-2-Mercapto-5-((5-methylfuran-2-yl)methylene)thiazol-4(5H)-one | 88674-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (E)-2-Mercapto-5-((5-methylfuran-2-yl)methylene)thiazol-4(5H)-one
• 英文别名: 5-[(5-methylfuran-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 88674-82-2
• 化学式: C₉H₇NO₂S₂
• mdl: MFCD03423525
• 分子量: 225.292
• InChiKey: UIWYMDIBJKBBKW-UHFFFAOYSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (E)-2-Mercapto-5-((5-methylfuran-2-yl)methylene)thiazol-4(5H)-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 以90%的产率得到N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-[(5-methylfuran-2-yl)methyl-ene]-2-thioxo-4-thiazolidinone
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some new N-glycosides of 2-thioxo-4-thiazolidinone derivatives

  摘要：

  5-Arylidene-2-thioxo-4-thiazolidinones 3a-f react with each of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and alpha-D-galactopyranosyl bromides 4a,b in acetone in the presence of aqueous potassium hydroxide at room temperature to afford N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) or N-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl) 2-thioxo-4-thiazolidinone derivatives 5a-f. Similarly, the reaction of 5-cycloalkylidene-2-thioxo-4-thiazolidinones 7a,b with 4a gave the corresponding N-glucosides 8a,b. Also, 5-pyrazolidene rhodanines 10a-e react with 4a to afford the new N-glucosides 11a-e. Treatment of compounds 15 and 16 with 4a in the presence of few drops of triethylamine or in KOH solution accomplished the mono- and bis-nucleosides 17 and 18, respectively. Some selected products were tested for their antimicrobial activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.04.011
• 作为产物：
  描述：

  5-甲基呋喃醛 、 罗丹宁 以92 %的产率得到(E)-2-Mercapto-5-((5-methylfuran-2-yl)methylene)thiazol-4(5H)-one
  参考文献：
  名称：

  L-脯氨酸基低共熔溶剂中5-芳基罗丹宁的合成

  摘要：

  摘要 已知绕丹宁及其衍生物具有许多可通过不同功能化位点调节的药理活性。这些支架中研究最多的修饰之一是通过 Knoevenagel 反应在 C5 上引入亚苄基部分。在此，报道了在基于 ʟ-脯氨酸的低共熔溶剂 (DES) 中通过 Knoevenagel 反应轻松合成 5-arylidenerhodanines。该方法快速（60°C 下 1 小时）、简单、无催化剂且可持续，因为不使用经典有机溶剂。水解后通过简单过滤即可回收预期化合物，无需纯化。研究了这些衍生物的抗氧化活性，结果与文献报道一致，表明酚类化合物的活性更高。 贝尔斯坦 J. 组织。化学。 2023, 19, 1537–1544。doi:10.3762/bjoc.19.110

  DOI：

  10.3762/bjoc.19.110

文献信息

• Coumarin derivative and use thereof
  申请人：Morinaga Milk Industry Co., Ltd.

  公开号：US05574062A1

  公开（公告）日：1996-11-12

  The present invention provides compounds having 12-lipoxygenase inhibitory effect and medicines inhibiting 12-lipoxygenase selectively, and relates to novel coumarin derivatives and medicines containing the compounds as effective ingredients. Furthermore, this invention relates to compounds capable of converting to compounds inhibiting 12-lipoxygenase activities selectively according to the cleavage of modified moieties in vivo and medicines inhibiting 12-lipoxygenase selectively, and relates to novel coumarin derivatives having acyl groups as modified moieties and medicines containing the compounds as effective ingredients. The compounds of the present invention can inhibit 12-lipoxygenase strongly and selectively, and being useful as medicines for preventing and treating various circulatory diseases such as arteriosclerosis and vasospasm and for preventing of the metastasis of some kinds of cancers, and show low toxicity and few side effects.

  本发明提供了具有12-脂氧合酶抑制作用的化合物和选择性抑制12-脂氧合酶的药物，并涉及新型香豆素衍生物和含有该化合物作为有效成分的药物。此外，本发明还涉及能够在体内通过修饰基团的断裂转化为选择性抑制12-脂氧合酶活性的化合物和选择性抑制12-脂氧合酶的药物，并涉及具有酰基作为修饰基团的新型香豆素衍生物和含有该化合物作为有效成分的药物。本发明的化合物可以强烈而选择性地抑制12-脂氧合酶，并可用作预防和治疗各种循环系统疾病，如动脉硬化和血管痉挛以及预防某些癌症的转移的药物，并显示出低毒性和少量副作用。
• Synthesis and antimicrobial activity of some new N-glycosides of 2-thioxo-4-thiazolidinone derivatives
  作者：Nadia Hanafy Metwally、Magda Ahmed Abdalla、Mosselhi Abdel Nabi Mosselhi、Ebrahim Adel El-Desoky

  DOI：10.1016/j.carres.2010.04.011

  日期：2010.6

  5-Arylidene-2-thioxo-4-thiazolidinones 3a-f react with each of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and alpha-D-galactopyranosyl bromides 4a,b in acetone in the presence of aqueous potassium hydroxide at room temperature to afford N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) or N-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl) 2-thioxo-4-thiazolidinone derivatives 5a-f. Similarly, the reaction of 5-cycloalkylidene-2-thioxo-4-thiazolidinones 7a,b with 4a gave the corresponding N-glucosides 8a,b. Also, 5-pyrazolidene rhodanines 10a-e react with 4a to afford the new N-glucosides 11a-e. Treatment of compounds 15 and 16 with 4a in the presence of few drops of triethylamine or in KOH solution accomplished the mono- and bis-nucleosides 17 and 18, respectively. Some selected products were tested for their antimicrobial activities. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent
  作者：Stéphanie Hesse

  DOI：10.3762/bjoc.19.110

  日期：——

  scaffolds is the introduction of a benzylidene moiety on C5 via a Knoevenagel reaction. Here, a facile synthesis of 5-arylidenerhodanines via a Knoevenagel reaction in an ʟ-proline-based deep eutectic solvent (DES) is reported. This method is fast (1 h at 60 °C), easy, catalyst-free and sustainable as no classical organic solvents were used. The expected compounds are recovered by a simple filtration

  摘要 已知绕丹宁及其衍生物具有许多可通过不同功能化位点调节的药理活性。这些支架中研究最多的修饰之一是通过 Knoevenagel 反应在 C5 上引入亚苄基部分。在此，报道了在基于 ʟ-脯氨酸的低共熔溶剂 (DES) 中通过 Knoevenagel 反应轻松合成 5-arylidenerhodanines。该方法快速（60°C 下 1 小时）、简单、无催化剂且可持续，因为不使用经典有机溶剂。水解后通过简单过滤即可回收预期化合物，无需纯化。研究了这些衍生物的抗氧化活性，结果与文献报道一致，表明酚类化合物的活性更高。 贝尔斯坦 J. 组织。化学。 2023, 19, 1537–1544。doi:10.3762/bjoc.19.110