N-[4-(1,3-Benzothiazol-2-yl)phenyl]-2-bromoacetamide | 886012-82-4

• 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: N-[4-(1,3-Benzothiazol-2-yl)phenyl]-2-bromoacetamide
• CAS: 886012-82-4
• 化学式: C₁₅H₁₁BrN₂OS
• 分子量: 347.2
• InChiKey: LALVUBXXRTXFAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[[3-(trifluoromethyl)phenyl]methylidene]-1,3-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60 %的产率得到N‐[4‐(benzo[d]thiazol‐2‐yl)phenyl]‐2‐{5‐[3‐(trifluoromethyl)benzylidene]‐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-氨基苯硫醇 在 potassium carbonate 、 氯化铵 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.5h， 生成 N-[4-(1,3-Benzothiazol-2-yl)phenyl]-2-bromoacetamide
  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

文献信息

• Compounds for Imaging and Therapy
  申请人：Dilworth Jonathan Robin

  公开号：US20110098353A1

  公开（公告）日：2011-04-28

  A metal complex of formula (III) wherein: M is a transition metal and A1, A2, X, X′, Y, L1′, R1′ and R2′ are as defined herein, is useful in medical imaging and therapy.

  公式（III）的金属配合物，其中：M是过渡金属，A1，A2，X，X'，Y，L1'，R1'和R2'的定义如本文所述，可用于医学成像和治疗。
• US8299285B2
  申请人：——

  公开号：US8299285B2

  公开（公告）日：2012-10-30
• [EN] COMPOUNDS FOR IMAGING AND THERAPY<br/>[FR] COMPOSES D'IMAGERIE ET DE TRAITEMENT
  申请人：ISIS INNOVATION

  公开号：WO2007003944A2

  公开（公告）日：2007-01-11

  [EN] A metal complex of formula (III) wherein: M is a transition metal and Al, A2, X, X', Y, Ll', Rl' and R2' are as defined herein, is useful in medical imaging and therapy.
  [FR] L'invention concerne un complexe métallique représenté par la formule (III), dans laquelle M représente un métal de transition et A1, A2, X, X', Y, L1', R1' et R2' sont tels que définis dans la demande. Le complexe est utile dans l'imagerie médicale et comme traitement.