5-(3,5-dimethoxybenzylidene)thiazolidine-2,4-dione | 313957-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3,5-dimethoxybenzylidene)thiazolidine-2,4-dione
• 英文别名: 2,4-Thiazolidinedione, 5-[(3,5-dimethoxyphenyl)methylene]-；5-[(3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 313957-99-2
• 化学式: C₁₂H₁₁NO₄S
• mdl: MFCD01230060
• 分子量: 265.29
• InChiKey: VRHTYBLWNKWMQB-UHFFFAOYSA-N

物化性质

• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3,5-dimethoxybenzylidene)thiazolidine-2,4-dione 、 N-[4-(1,3-Benzothiazol-2-yl)phenyl]-2-bromoacetamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62 %的产率得到N‐[4‐(benzo[d]thiazol‐2‐yl)phenyl]‐2‐[5‐(3,5‐dimethoxybenzylidene)‐2,4‐dioxothiazolidin‐3‐yl]acetamide
  参考文献：
  名称：

  10.1002/ardp.202400504

  摘要：

  AbstractThe oncogenic transcription factor FOXM1 overexpressed in breast and other solid cancers, is a key driver of tumor growth and progression through complex interactions, making it an attractive molecular target for the development of targeted therapies. Despite the availability of small‐molecule inhibitors, their limited specificity, potency, and efficacy hinder clinical translation. To identify effective FOXM1 inhibitors, we synthesized novel benzothiazole derivatives (KC10–KC13) and benzothiazole hybrids with thiazolidine‐2,4‐dione (KC21–KC36). These compounds were evaluated for FOXM1 inhibition. Molecular docking and molecular dynamics simulation analysis revealed their binding patterns and affinities for the FOXM1‐DNA binding domain. The interactions with key amino acids such as Asn283, His287, and Arg286, crucial for FOXM1 inhibition, have been determined with the synthesized compounds. Additionally, the molecular modeling study indicated that KC12, KC21, and KC30 aligned structurally and interacted similarly to the reference compound FDI‐6. In vitro studies with the MDA‐MB‐231 breast cancer cell line demonstrated that KC12, KC21, and KC30 significantly inhibited FOXM1, showing greater potency than FDI‐6, with IC50 values of 6.13, 10.77, and 12.86 µM, respectively, versus 20.79 µM for FDI‐6. Our findings suggest that KC12, KC21, and KC30 exhibit strong activity as FOXM1 inhibitors and may be suitable for in vivo animal studies.

  DOI：

  10.1002/ardp.202400504
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 3,5-二甲氧基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以98%的产率得到5-(3,5-dimethoxybenzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  미세조류 파괴용 조성물

  摘要：

  本发明涉及微藻破坏性配方，所述微藻破坏性配方被处理在海洋微藻培养场、褐藻或红藻爆发区域或者预计褐藻或红藻爆发的区域，通过抑制微藻的生长和繁殖，可以预防褐藻和红藻的危害。

  公开号：

  KR20160126772A