2,4-diphenyl-5-oxo-1,2,4-thiadiazolidine-3-thione | 100537-34-6

• 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: 2,4-diphenyl-5-oxo-1,2,4-thiadiazolidine-3-thione
• 英文别名: 1,2,4-Thiadiazolidin-5-one, 2,4-diphenyl-3-thioxo-；2,4-diphenyl-3-sulfanylidene-1,2,4-thiadiazolidin-5-one
• CAS: 100537-34-6
• 化学式: C₁₄H₁₀N₂OS₂
• 分子量: 286.378
• InChiKey: PRDNKKPIALEDSB-UHFFFAOYSA-N

物化性质

• 熔点：
  105-110 °C
• 沸点：
  404.5±28.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫代异氰酸苯酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 air 、 氯 作用下， 以 正己烷 为溶剂， 反应 8.0h， 生成 2,4-diphenyl-5-oxo-1,2,4-thiadiazolidine-3-thione
  参考文献：
  名称：

  First Non-ATP Competitive Glycogen Synthase Kinase 3 β (GSK-3β) Inhibitors:  Thiadiazolidinones (TDZD) as Potential Drugs for the Treatment of Alzheimer's Disease

  摘要：

  Glycogen synthase kinase 3beta (GSK-3beta) has a central role in Alzheimer's disease (AD). Selective inhibitors which avoid tau hyperphosphorylation may represent an effective therapeutical approach to the AD pharmacotherapy and other neurodegenerative disorders. Here, we describe the synthesis, biological evaluation, and SAR of the small heterocyclic thiadiazolidinones (TDZD) as the first non-ATP competitive inhibitor of GSK-3beta. Their synthesis is based on the reactivity of sulfenyl chlorides. In GSK-3beta assays, TDZD derivatives showed IC50 values in the micromolar range, whereas in other protein kinases assays they were devoid of any inhibitory activity. SAR studies allowed the identification of the key structural features. Finally, a possible enzymatic binding mode is proposed.

  DOI：

  10.1021/jm011020u

文献信息

• [EN] METHODS AND COMPOSITIONS FOR MODULATING HAIR GROWTH, WOUND HEALING AND SCAR REVISION<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR MODULER LA POUSSE DE CHEVEUX, LA CICATRISATION DE PLAIE ET LA RÉVISION DE CICATRICE
  申请人：FOLLICA INC

  公开号：WO2012065065A9

  公开（公告）日：2012-10-11

  [EN] The invention relates to methods for (i) modulating hair growth and (ii) improving wound healing, e.g., scarless wound healing, and scar revision in human subjects involving the administration of one or more compounds provided herein. Compositions and uses of compositions containing the compounds provided herein are also described. The compound, composition thereof, or treatment(s) comprising the compound may be administered alone or in combination with (e.g., concurrently with, before, and/or after) other treatments for the enhancement or inhibition of hair growth or for the improvement of wound healing or scar revision. Such combination treatments may involve mechanical or physical treatments that cause integumental perturbation (e.g., laser, dermabrasion, etc.); immune stimulation; chemical treatments; and/or surgical treatments for the enhancement or inhibition of hair growth or for the improvement of wound healing or scar revision.
  [FR] L'invention porte sur des procédés pour (i) moduler la pousse de cheveux et (ii) améliorer la cicatrisation de plaie, par exemple, la cicatrisation de plaie sans cicatrice, et la révision de cicatrice chez des sujets humains, lesquels procédés comprennent l'administration d'un ou plusieurs composés décrits présentement. L'invention porte également sur des compositions et sur des utilisations de compositions contenant les composés décrits présentement. Le composé, sa composition ou le ou les traitements comprenant le composé peuvent être administrés seuls ou en combinaison avec (par exemple, simultanément avec, avant et/ou après) d'autres traitements pour l'amélioration ou l'inhibition de la pousse de cheveux ou l'amélioration de la cicatrisation de plaie ou de la révision de cicatrice. De tels traitements combinés peuvent comprendre des traitements mécaniques ou physiques qui provoquent une perturbation tégumentaire (par exemple, laser, dermabrasion, etc.); une stimulation immunitaire; des traitements chimiques; et/ou des traitements chirurgicaux pour l'amélioration ou l'inhibition de la pousse de cheveux ou l'amélioration de la cicatrisation de plaie ou de la révision de cicatrice.
• First Non-ATP Competitive Glycogen Synthase Kinase 3 β (GSK-3β) Inhibitors:  Thiadiazolidinones (TDZD) as Potential Drugs for the Treatment of Alzheimer's Disease
  作者：Ana Martinez、Mercedes Alonso、Ana Castro、Concepción Pérez、Francisco J. Moreno

  DOI：10.1021/jm011020u

  日期：2002.3.1

  Glycogen synthase kinase 3beta (GSK-3beta) has a central role in Alzheimer's disease (AD). Selective inhibitors which avoid tau hyperphosphorylation may represent an effective therapeutical approach to the AD pharmacotherapy and other neurodegenerative disorders. Here, we describe the synthesis, biological evaluation, and SAR of the small heterocyclic thiadiazolidinones (TDZD) as the first non-ATP competitive inhibitor of GSK-3beta. Their synthesis is based on the reactivity of sulfenyl chlorides. In GSK-3beta assays, TDZD derivatives showed IC50 values in the micromolar range, whereas in other protein kinases assays they were devoid of any inhibitory activity. SAR studies allowed the identification of the key structural features. Finally, a possible enzymatic binding mode is proposed.