3-氯-5-[(苯基甲基)硫代]-1,2,4-噻二唑 | 36598-31-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-氯-5-[(苯基甲基)硫代]-1,2,4-噻二唑
• 英文名称: 3-Chlor-5-benzylthio-1,2,4-thiadiazol
• 英文别名: 5-benzylsulfanyl-3-chloro-[1,2,4]thiadiazole；5-(Benzylthio)-3-chloro-1,2,4-thiadiazole；5-benzylsulfanyl-3-chloro-1,2,4-thiadiazole
• CAS: 36598-31-9
• 化学式: C₉H₇ClN₂S₂
• mdl: MFCD02948844
• 分子量: 242.753
• InChiKey: YXAXEKHYAISKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氯-5-[(苯基甲基)硫代]-1,2,4-噻二唑 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 3-chloro-5-phenylmethanesulfonyl-[1,2,4]thiadiazole
  参考文献：
  名称：

  Chemistry of N-cyanodithioimidocarbonic acid. II. Synthesis of 3-halo-1,2,4-thiadiazoles

  摘要：

  DOI：

  10.1021/jo00943a011
• 作为产物：
  描述：

  氰基二硫代亚氨酸 S-苄酯 S-钾盐 在 磺酰氯 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 3-氯-5-[(苯基甲基)硫代]-1,2,4-噻二唑
  参考文献：
  名称：

  3‐Chloro‐5‐Substituted‐1,2,4‐Thiadiazoles (TDZs) as Selective and Efficient Protein Thiol Modifiers

  摘要：

  AbstractThe study of cysteine modifications has gained much attention in recent years. This includes detailed investigations in the field of redox biology with focus on numerous redox derivatives like nitrosothiols, sulfenic acids, sulfinic acids and sulfonic acids resulting from increasing oxidation, S‐lipidation, and perthiols. For these studies selective and rapid blocking of free protein thiols is required to prevent disulfide rearrangement. In our attempt to find new inhibitors of human histone deacetylase 8 (HDAC8) we discovered 5‐sulfonyl and 5‐sulfinyl substituted 1,2,4‐thiadiazoles (TDZ), which surprisingly show an outstanding reactivity against thiols in aqueous solution. Encouraged by these observations we investigated the mechanism of action in detail and show that these compounds react more specifically and faster than commonly used N‐ethyl maleimide, making them superior alternatives for efficient blocking of free thiols in proteins. We show that 5‐sulfonyl‐TDZ can be readily applied in commonly used biotin switch assays. Using the example of human HDAC8, we demonstrate that cysteine modification by a 5‐sulfonyl‐TDZ is easily measurable using quantitative HPLC/ESI‐QTOF‐MS/MS, and allows for the simultaneous measurement of the modification kinetics of seven solvent‐accessible cysteines in HDAC8.

  DOI：

  10.1002/cbic.202200417