4-hydroxy-6-methoxy-2H-chromene-2-thione | 1407546-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-hydroxy-6-methoxy-2H-chromene-2-thione
• CAS: 1407546-83-1
• 化学式: C₁₀H₈O₃S
• 分子量: 208.238
• InChiKey: AUWCZICWKHUYFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methoxy-2H-chromene-2-thione 在 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 6-Methoxy-2-[4-(4-methoxyphenyl)piperazin-1-yl]chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

  摘要：

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.071
• 作为产物：
  描述：

  二硫化碳 、 2'-羟基-5'-甲氧基苯乙酮 在 potassium tert-butylate 、 硫酸 作用下， 以 苯 、 水 为溶剂， 反应 34.0h， 以55%的产率得到4-hydroxy-6-methoxy-2H-chromene-2-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

  摘要：

  A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-alpha and 70-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 mu M) while the compounds5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.071

文献信息

• l-Proline-catalysed synthesis of chromeno[2,3-b]chromene from 4-hydroxy-2H-chromene-2-thione and an anti-proliferative study
  作者：Arnab Mandal、Satyajit Singh、Arisha Arora、Sujisha S. Nambiar、Siddhartha S. Ghosh、Abu Taleb Khan

  DOI：10.1039/d4ob00509k

  日期：——

  investigated with aryl aldehydes and 5,5-dimethylcylohexane-1,3-dione (dimedone) in the presence of 20 mol% L-proline in toluene at 90 °C. Instead of the expected linear product with a sulphur atom in the ring provided by 4-hydroxydithiocoumarin or an angular product obtained from 4-hydroxycoumarin, the hitherto unreported products, 12-aryl substituted chromeno[2,3-b]chromenes (4), were obtained in good to excellent

  在 20 mol% L-脯氨酸的甲苯溶液中，90 ° 下，研究了 4-羟基-2 H-色烯-2-硫酮与芳基醛和 5,5-二甲基环己烷-1,3-二酮（双甲酮）的反应性C.代替预期由 4-羟基二硫代香豆素提供的环中具有硫原子的线性产物或由 4-羟基香豆素获得的有角产物，迄今为止未报道的产物，12-芳基取代的色烯[2,3- b ]色烯 ( 4 )，获得了良好至优异的产量。该反应通过三组分反应进行，先通过双甲酮与芳香醛之间的 Knoevenagel 缩合，然后与 4-羟基-2H-色烯-2-硫酮进行 Michael 加成。此外，对所有衍生物进行了分子对接研究，其中四种化合物在乳腺癌（MCF7）细胞系中表现出抗增殖活性和增加的ROS生成。