5-[5-(3-chloro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one | 330570-41-7

• 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-[5-(3-chloro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one
• 英文别名: 5-[[5-(3-Chlorophenyl)furan-2-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 330570-41-7
• 化学式: C₁₄H₈ClNO₂S₂
• mdl: MFCD00298829
• 分子量: 321.808
• InChiKey: QRVTWPJZFXYJFK-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[5-(3-chloro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 16.33h， 生成 (Z)-5-((5-(3-chlorophenyl)furan-2-yl)methylene)-2-((4-fluorophenethyl)amino) thiazol-4(5H)-one
  参考文献：
  名称：

  Aminothiazolones as potent, selective and cell active inhibitors of the PIM kinase family

  摘要：

  We have previously reported the discovery of a series of rhodanine-based inhibitors of the PIM family of serine/threonine kinases. Here we described the optimisation of those compounds to improve their physicochemical and ADME properties as well as reducing their off-targets activities against other kinases. Through molecular modeling and systematic structure activity relationship (SAR) studies, advanced molecules with high inhibitory potency, reduced off-target activity and minimal efflux were identified as new pan-PIM inhibitors. One example of an early lead, OX01401, was found to inhibit PIMs with nanomolar potency (15 nM for PIM1), inhibit proliferation of two PIM-expressing leukaemic cancer cell lines, MV4-11 and K562, and to reduce intracellular phosphorylation of a PIM substrate in a concentration dependent manner.

  DOI：

  10.1016/j.bmc.2020.115724
• 作为产物：
  描述：

  罗丹宁 、 5-(3-氯苯基)糠醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 5-[5-(3-chloro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Aminothiazolones as potent, selective and cell active inhibitors of the PIM kinase family

  摘要：

  We have previously reported the discovery of a series of rhodanine-based inhibitors of the PIM family of serine/threonine kinases. Here we described the optimisation of those compounds to improve their physicochemical and ADME properties as well as reducing their off-targets activities against other kinases. Through molecular modeling and systematic structure activity relationship (SAR) studies, advanced molecules with high inhibitory potency, reduced off-target activity and minimal efflux were identified as new pan-PIM inhibitors. One example of an early lead, OX01401, was found to inhibit PIMs with nanomolar potency (15 nM for PIM1), inhibit proliferation of two PIM-expressing leukaemic cancer cell lines, MV4-11 and K562, and to reduce intracellular phosphorylation of a PIM substrate in a concentration dependent manner.

  DOI：

  10.1016/j.bmc.2020.115724

文献信息

• PREMATURE-TERMINATION-CODONS READTHROUGH COMPOUNDS
  申请人：GATTI Richard A.

  公开号：US20130274283A1

  公开（公告）日：2013-10-17

  Premature termination codons readthrough compounds, composition thereof, and methods of making and using the same are provided.

  提供了关于早期终止密码子读穿化合物、其组合物以及制备和使用方法的信息。
• 2-thioxothiazolidin-4-one compounds and compositions as antimicrobial and antimalarial agents targeting enoyl-ACP reductase of type II fatty acid synthesis pathway and other cell growth pathways
  申请人：National Institute of Immunology

  公开号：EP1834642A2

  公开（公告）日：2007-09-19

  The current invention presents enoyl-ACP reductase, an enzyme of the type II fatty acid synthesis pathway as a target for treating human malarias and other infectious diseases. We also present in the current invention, 2-thioxothiazolidin-4-ones as antimicrobial and antimalarial agents. We provide 2-thioxothiazolidin-4-ones as antimicrobial and antimalarial agents either alone or in combination with other known antimicrobial and antimalarial agents with or without added adjuvants or diluents or carriers.

  本发明将 II 型脂肪酸合成途径中的一种酶--烯酰-ACP 还原酶作为治疗人类疟疾和其他传染性疾病的靶标。本发明还提出了作为抗菌剂和抗疟药物的 2-硫酮噻唑烷-4-酮。我们提供 2-硫酮噻唑烷-4-酮作为抗菌剂和抗疟药物，可以单独使用，也可以与其他已知的抗菌剂和抗疟药物结合使用，可以添加佐剂或稀释剂或载体，也可以不添加佐剂或稀释剂或载体。
• 2-Thioxothiazolidin-4-one compounds and compositions as antimicrobial and antimalarial agents targeting enoyl-ACP reductase of type II fatty acid synthesis pathway and other cell growth pathways
  申请人：Surolia Avadhesha

  公开号：US20080051445A1

  公开（公告）日：2008-02-28

  The current invention presents enoyl-ACP reductase, an enzyme of the type II fatty acid synthesis pathway as a target for treating human malarias and other infectious diseases. We also present in the current invention, 2-thioxothiazolidin-4-ones as antimicrobial and antimalarial agents. We provide 2-thioxothiazolidin-4-ones as antimicrobial and antimalarial agents either alone or in combination with other known antimicrobial and antimalarial agents with or without added adjuvants or diluents or carriers.
• US9255088B2
  申请人：——

  公开号：US9255088B2

  公开（公告）日：2016-02-09
• [EN] PREMATURE-TERMINATION-CODONS READTHROUGH COMPOUNDS<br/>[FR] COMPOSÉS DE LECTURE ININTERROMPUE DE CODONS DE TERMINAISON PRÉMATURÉS (PTC)
  申请人：UNIV CALIFORNIA

  公开号：WO2012021707A2

  公开（公告）日：2012-02-16

  Premature termination codons readthrough compounds, composition thereof, and methods of making and using the same are provided.