4-(5-amino-1,3,4-thiadiazol-2-yl)butanoic acid | 933705-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-amino-1,3,4-thiadiazol-2-yl)butanoic acid
• 英文别名: 4-(5-Amino-1,3,4-thiadiazol-2-yl)butanoic acid
• CAS: 933705-06-7
• 化学式: C₆H₉N₃O₂S
• 分子量: 187.222
• InChiKey: NEADBMMZXPQSPL-UHFFFAOYSA-N

物化性质

• 沸点：
  455.0±47.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(5-amino-1,3,4-thiadiazol-2-yl)butanoic acid 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 100.0h， 生成 N-[5-[3-(5-amino-1,3,4-thiadiazol-2-yl)propyl]-1,3,4-thiadiazol-2-yl]-2-phenylacetamide
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl Sulfide 3 (BPTES) Analogs as Glutaminase Inhibitors

  摘要：

  Bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide (BPTES) is a potent and selective allosteric inhibitor of kidney-type glutaminase (GLS) that has served as a molecular probe to determine the therapeutic potential of GLS inhibition. In an attempt to identify more potent GLS inhibitors with improved drug-like molecular properties, a series of BPTES analogs were synthesized and evaluated. Our structure activity relationship (SAR) studies revealed that some truncated analogs retained the potency of BPTES, presenting an opportunity to improve its aqueous solubility. One of the analogs, N-(5-{2-[2-(5-amino-[1,3,4]thiadiazol-2-yl)-ethylsulfanyl]-ethyl}-[1,3,4]thiadiazol-2-yl)-2-phenylacetamide 6, exhibited similar potency and better solubility relative to BPTES and attenuated the growth of P493 human lymphoma B cells in vitro as well as in a mouse xenograft model.

  DOI：

  10.1021/jm301191p
• 作为产物：
  描述：

  4-氯甲酰基丁酸甲酯 、 氨基硫脲 在 三氯氧磷 作用下， 反应 5.0h， 以72%的产率得到4-(5-amino-1,3,4-thiadiazol-2-yl)butanoic acid
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl Sulfide 3 (BPTES) Analogs as Glutaminase Inhibitors

  摘要：

  Bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide (BPTES) is a potent and selective allosteric inhibitor of kidney-type glutaminase (GLS) that has served as a molecular probe to determine the therapeutic potential of GLS inhibition. In an attempt to identify more potent GLS inhibitors with improved drug-like molecular properties, a series of BPTES analogs were synthesized and evaluated. Our structure activity relationship (SAR) studies revealed that some truncated analogs retained the potency of BPTES, presenting an opportunity to improve its aqueous solubility. One of the analogs, N-(5-{2-[2-(5-amino-[1,3,4]thiadiazol-2-yl)-ethylsulfanyl]-ethyl}-[1,3,4]thiadiazol-2-yl)-2-phenylacetamide 6, exhibited similar potency and better solubility relative to BPTES and attenuated the growth of P493 human lymphoma B cells in vitro as well as in a mouse xenograft model.

  DOI：

  10.1021/jm301191p