4-chloro-3-methyl-2-oxo-2,3-dihydrothiazole-5-carbaldehyde | 57805-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chloro-3-methyl-2-oxo-2,3-dihydrothiazole-5-carbaldehyde
• 英文别名: 4-Chloro-3-methyl-2-oxo-2,3-dihydro-1,3-thiazole-5-carbaldehyde；4-chloro-3-methyl-2-oxo-1,3-thiazole-5-carbaldehyde
• CAS: 57805-14-8
• 化学式: C₅H₄ClNO₂S
• mdl: MFCD00708867
• 分子量: 177.611
• InChiKey: UZEXESAVNCYSNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-3-methyl-2-oxo-2,3-dihydrothiazole-5-carbaldehyde 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 甲酸铵 、 sodium hydride 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 29.5h， 生成 2-(6-(4-chlorophenyl)-8-methoxy-1-methyl-2-oxo-1,4-dihydro-2H-benzo[c]thiazolo[4,5-e]azepin-4-yl)-N-(4-hydroxyphenyl)acetamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 6-phenyl-1,3a,4,10b-tetrahydro-2H-benzo[c]thiazolo[4,5-e]azepin-2-one derivatives as potential BRD4 inhibitors

  摘要：

  Bromodomain-containing protein 4 (BRD4) is a key epigenetic regulator in cancer, and inhibitors targeting BRD4 exhibit great anticancer activity. By replacing the methyltriazole ring of the BRD4 inhibitor I-BET-762 with an N-methylthiazolidone heterocyclic ring, fifteen novel BRD4 inhibitors were designed and synthesized. Compound 13f had a hydrophobic acetylcyclopentanyl side chain, showing the most potent BRD4 inhibitory activity in the BRD4-BD1 inhibition assay (IC50, value of 110 nM), it also significantly suppressed the proliferation of MV-4-11 cells with high BRD4 level (IC50, value of 0.42 mu M). Furthermore, the potent apoptosis-promoting and G0/G1 cycle-arresting activity of compound 13f were indicated by flow cytometry. As the downstream-protein of BRD4, c-Myc was in significantly low expression by compound 13f treatment in a dose-dependent manner. All the findings supported that this novel compound 13f provided a perspective for developing effective BRD4 inhibitors.

  DOI：

  10.1016/j.bmc.2020.115601
• 作为产物：
  描述：

  3-甲基-1,3-噻唑烷-2,4-二酮 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以79%的产率得到4-chloro-3-methyl-2-oxo-2,3-dihydrothiazole-5-carbaldehyde
  参考文献：
  名称：

  [EN] INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES
  [FR] INHIBITEURS DE RÉPLICATION VIRALE, LEUR PROCÉDÉ DE SYNTHÈSE ET LEURS APPLICATIONS THÉRAPEUTIQUES

  摘要：

  本发明涉及权利要求1中所述的式(1)化合物，及其用于治疗或预防病毒疾病，包括HIV。

  公开号：

  WO2012137181A1

文献信息

• NOVEL TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160176864A1

  公开（公告）日：2016-06-23

  The present invention is directed to tricyclic compounds, pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及三环化合物，包括本发明化合物的药用可接受组合物以及在治疗各种疾病中使用所述组合物的方法。
• [EN] TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS<br/>[FR] COMPOSÉS TRICYCLIQUES COMME AGENTS ANTI-CANCERS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015100282A1

  公开（公告）日：2015-07-02

  The present invention is directed to tricyclic compounds (I), pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及三环化合物（I），包括本发明化合物的药用可接受组合物以及使用所述组合物治疗各种疾病的方法。
• INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES
  申请人：Chasset Sophie

  公开号：US20140128383A1

  公开（公告）日：2014-05-08

  The present invention relates to compounds, their use in the treatment or the prevention of viral disorders, including HIV.

  本发明涉及化合物及其在治疗或预防病毒性疾病，包括HIV方面的应用。
• Inhibitors of viral replication, their process of preparation and their therapeutical uses
  申请人：Chasset Sophie

  公开号：US09238026B2

  公开（公告）日：2016-01-19

  The present invention relates to compounds, their use in the treatment or the prevention of viral disorders, including HIV.

  本发明涉及化合物及其在治疗或预防病毒性疾病，包括HIV方面的应用。
• TRICYCLIC COMPOUND AS ANTICANCER AGENTS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3466949A1

  公开（公告）日：2019-04-10

  The present invention is directed to tricyclic compounds, pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及三环化合物、包含本发明化合物的药学上可接受的组合物以及使用所述组合物治疗各种疾病的方法。