5,5′-thiobis(methylene)bis(1,3,4-thiadiazol-2-amine) | 312607-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,5′-thiobis(methylene)bis(1,3,4-thiadiazol-2-amine)
• 英文别名: 5,5'-(Thiobis(methylene))bis(1,3,4-thiadiazol-2-amine)；5-[(5-amino-1,3,4-thiadiazol-2-yl)methylsulfanylmethyl]-1,3,4-thiadiazol-2-amine
• CAS: 312607-90-2
• 化学式: C₆H₈N₆S₃
• 分子量: 260.368
• InChiKey: AMDXXWJGCHBZRI-UHFFFAOYSA-N

物化性质

• 沸点：
  539.1±60.0 °C(Predicted)
• 密度：
  1.697±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 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：
  185
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5,5′-thiobis(methylene)bis(1,3,4-thiadiazol-2-amine) 、 苯乙酰氯 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以40%的产率得到N,N'-(5,5′-thiobis(methylene)bis(1,3,4-thiadiazole-5,2-diyl))bis(2-phenylacetamide)
  参考文献：
  名称：

  Allosteric kidney-type glutaminase (GLS) inhibitors with a mercaptoethyl linker

  摘要：

  A series of allosteric kidney-type glutaminase (GLS) inhibitors possessing a mercaptoethyl (-SCH2CH2-) linker were synthesized in an effort to further expand the structural diversity of chemotypes derived from bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide (BPTES), a prototype allosteric inhibitor of GLS. BPTES analog 3a with a mercaptoethyl linker between the two thiadiazole rings was found to potently inhibit GLS with an IC50 value of 50 nM. Interestingly, the corresponding derivative with an n-propyl (-CH2CH2CH2-) linker showed substantially lower inhibitory potency (IC50 = 2.3 mu M) while the derivative with a dimethylsulfide (-CH2SCH2-) linker showed no inhibitory activity at concentrations up to 100 mu M, underscoring the critical role played by the mercaptoethyl linker in the high affinity binding to the allosteric site of GLS. Additional mercaptoethyl-linked compounds were synthesized and tested as GLS inhibitors to further explore SAR within this scaffold including derivatives possessing a pyridazine as a replacement for one of the two thiadiazole moiety.Y

  DOI：

  10.1016/j.bmc.2020.115698
• 作为产物：
  描述：

  硫代二乙酸 、 氨基硫脲 在 三氯氧磷 作用下， 反应 5.0h， 生成 5,5′-thiobis(methylene)bis(1,3,4-thiadiazol-2-amine)
  参考文献：
  名称：

  [EN] HETEROCYCLIC INHIBITORS OF GLUTAMINASE
  [FR] INHIBITEURS HÉTÉROCYCLIQUES DE GLUTAMINASE

  摘要：

  本发明涉及式(I)定义的杂环化合物及其药物制剂。本发明进一步涉及使用本发明的杂环化合物治疗癌症、免疫性或神经疾病的方法。

  公开号：

  WO2013078123A1

文献信息

• HETEROCYCLIC INHIBITORS OF GLUTAMINASE
  申请人：Calithera Biosciences Inc.

  公开号：US20130157998A1

  公开（公告）日：2013-06-20

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treatment using the novel heterocyclic compounds of the invention.

  本发明涉及新型杂环化合物及其制药制剂。本发明还涉及使用所述新型杂环化合物治疗的方法。
• TREATMENT OF CANCER WITH HETEROCYCLIC INHIBITORS OF GLUTAMINASE
  申请人：Calithera Biosciences, Inc.

  公开号：US20150004134A1

  公开（公告）日：2015-01-01

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  本发明涉及新型杂环化合物及其制药制剂。本发明还涉及使用所述新型杂环化合物治疗或预防癌症的方法。
• Heterocyclic Inhibitors of Glutaminase
  申请人：Calithera Biosciences, Inc.

  公开号：US20200165238A1

  公开（公告）日：2020-05-28

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treatment using the novel heterocyclic compounds of the invention.
• US8865718B2
  申请人：——

  公开号：US8865718B2

  公开（公告）日：2014-10-21
• US9938267B2
  申请人：——

  公开号：US9938267B2

  公开（公告）日：2018-04-10