2-ethyl-4-phenethyl-1,2,4-thiadiazolidine-3,5-dione

• 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-ethyl-4-phenethyl-1,2,4-thiadiazolidine-3,5-dione
• 英文别名: 2-ethyl-4-(2-phenylethyl)-1,2,4-thiadiazolidine-3,5-dione
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: HYCIUMWKUONOEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基乙基异硫代氰酸酯 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-ethyl-4-phenethyl-1,2,4-thiadiazolidine-3,5-dione
  参考文献：
  名称：

  Tideglusib and Its Analogues As Inhibitors of Staphylococcus aureus SrtA

  摘要：

  Sortase A (SrtA) anchors surface proteins to the cell wall envelope, and it has attracted increasing interesting as a potential antivirulence target. Several small-molecule inhibitors for SrtA have been developed, but target validation remains largely underexplored. Herein, we report a new class of SrtA inhibitors that supports antivirulence therapy through small-molecule targeting of SrtA. Tideglusib (TD), a drug candidate for myotonic dystrophy, was outstanding in high-throughput screening. A concise synthetic route quickly provided TD analogues, and the structure-activity relationships for SrtA inhibition have been established from those analogues. Several compounds largely retained the in vitro potency and exhibited a better solubility than TD. Additionally, TD attenuated virulence-related phenotypes in vitro and protected mice against lethal S. aureus USA300 bacteremia. Our study indicates that TD and its analogues could be new candidates as SrtA inhibitors with potential in the development of new antivirulence agents.

  DOI：

  10.1021/acs.jmedchem.0c00803

文献信息

• Enzyme inhibitors
  申请人：——

  公开号：US20030195238A1

  公开（公告）日：2003-10-16

  Compounds of general formula (I): 1 where A, E, G, X, Y and the bond - - - take various meanings are of use in the preparation of a pharmaceutical formulation, for example in the treatment of a disease in which GSK-3 is involved, including Alzheimer's disease or the non-dependent insulin diabetes mellitus, or hyperproliferative disease such as cancer, displasias or metaplasias of tissue, psoriasis, arteriosclerosis or restenosis.

  通式（I）的化合物： 其中A、E、G、X、Y和键- - - 取不同含义，在制备药物配方中有用，例如在治疗涉及GSK-3的疾病中，包括阿尔茨海默病或非依赖胰岛素糖尿病，或高增殖性疾病，如癌症、组织发育不良或异型增生、银屑病、动脉硬化或再狭窄症。
• US6872737B2
  申请人：——

  公开号：US6872737B2

  公开（公告）日：2005-03-29
• US7666885B2
  申请人：——

  公开号：US7666885B2

  公开（公告）日：2010-02-23
• US7781463B2
  申请人：——

  公开号：US7781463B2

  公开（公告）日：2010-08-24
• [EN] THE USE OF 1, 2, 4-THIADIAZOLIDINE-3, 5-DIONES AS PPAR ACTIVATORS<br/>[FR] UTILISATION DE 1, 2, 4-THIADIAZOLIDINE-3, 5-DIONES EN TANT QU'ACTIVATEURS DE PPAR
  申请人：NEUROPHARMA SA

  公开号：WO2006045581A1

  公开（公告）日：2006-05-04

  [EN] The invention is related to the use of a family of structurally distinct compounds having a thiadiazolidine heterocycle core which are potent PPAR ligands and have good pharmacological properties, for the treatment of diseases or conditions that require PPAR activation or are PPAR mediated.
  [FR] L'invention concerne l'utilisation d'une famille de composés de structures distinctes possédant un noyau hétérocyclique de thiadiazolidine et constituant des ligands puissants de PPAR, tout en possédant de bonnes propriétés pharmacologiques. Ces composés servent à traiter des maladies ou des états nécessitant l'activation de PPAR ou dans lesquels PPAR jouent un rôle d'intermédiaire.