5-氨基-1,2,4-噻二唑-3-酮 | 59221-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1,2,4-噻二唑-3-酮
• 英文名称: 5-amino-2H-1,2,4-thiadiazolin-3-one
• 英文别名: 5-amino-1,2,4-thiadiazol-3(2H)-one；5-amino-2H-1,2,4-thiadiazol-3-one；5-amino-3-oxo-1,2,4-thiadiazole；5-amino-1,2,4-thiadiazole-3-one；5-Amino-1,2,4-thiadiazol-3-on；5-amino-1,2,4-thiadiazol-3-one
• CAS: 59221-06-6
• 化学式: C₂H₃N₃OS
• 分子量: 117.131
• InChiKey: MODAULMVTKWLKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氨基-1,2,4-噻二唑-3-酮 在 sodium hydroxide 作用下， 反应 1.0h， 生成 N-氰基-脲
  参考文献：
  名称：

  Piskala; Vachalkova; Masojidkova, Pharmazie, 2004, vol. 59, # 10, p. 756 - 762

  摘要：

  DOI：
• 作为产物：
  描述：

  硫代缩二脲 在 sodium hydroxide 作用下， 以 various solvent(s) 为溶剂， 生成 5-氨基-1,2,4-噻二唑-3-酮
  参考文献：
  名称：

  5-Amino-3-oxo-1,2,4-噻二唑的互变异构：实验和理论研究

  摘要：

  由于某些衍生物作为 GSK3 抑制剂的药理活性，1,2,4-噻二唑系统是我们研究的主题。因此，为了探索负责受体相互作用的活性形式，使用实验和理论方法对 5-amino-3-oxo-1,2,4-thiadiazole 系统中的互变异构现象进行了系统研究。因此，通过密度泛函理论和局部密度泛函方法在气相中研究了可能的互变异构体的相对稳定性。溶液中的理论研究是通过使用几种连续溶剂化模型进行的。最后，进行了实验研究以明确建立互变异构形式。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200700544

文献信息

• Aroylation of 5-amino-2<i>H</i>-1,2,4-thiadiazolin-3-one
  作者：Nam Sook Cho、Chan Soo Ra、Do Young Ra、Jin Soo Song、Sung Kwon Kang

  DOI：10.1002/jhet.5570330644

  日期：1996.11

  2-Aroyl-5-aroylamino-1,2,4-thiadiazolin-3-ones 2 have been synthesized through aroylation of 5-amino-2H-1,2,4-thiadiazolin-3-one (1) as an analog of cytosine. The aroylation was carried out with a substituted aroyl chloride in pyridine at 56–58°. It has been established that the intermediates of the reactions are 2-aroyl-5-amino-1,2,4-thiadiazolin-3-ones 3 on the basis of the spectral data, additional

  通过将5-氨基-2 H -1,2,4-噻二唑啉-3-one（1）芳香化，可以合成2-芳基-5-芳酰基氨基-1,2,4-噻二唑啉-3-酮2胞嘧啶。芳基化反应是在吡啶中于56–58°时用取代的芳酰氯进行的。根据光谱数据，另外的实验信息和从头算分子轨道计算，已经确定反应的中间体是2-芳酰基-5-氨基-1，2，4-噻二唑啉-3-酮3。
• Aroylation of 5-amino-2<i>H</i>-1,2,4-thiadiazolin-3-ones
  作者：Nam Sook Cho、Chan Soo Ra、Do Young Ra、Jin Soo Song、Sung Kwon Kang

  DOI：10.1002/jhet.5570330433

  日期：1996.7

  2-Aroyl-5-aroylamino-1,2,4-thiadiazolin-3-ones (2) have been synthesized through aroylation of 5-arruno-2H-1,2,4-thiadiazolin-3-one (1) as an analog of cytosine. The aroylation was carried out with a substituted aroyl chloride in pyridine at 56∼58°C. It has been established that the intermediates of the reactions are 2-aroyl-5-amino-1,2,4-thiadiazolin-3-ones (3) on the basis of the spectral data, additional

  通过5-arruno-2 H -1,2,4-噻二唑啉-3-one（1）的芳基化反应合成了2-Aroyl-5-aroylamino-1,2,4-thiadiazolin-3-ones（2）。胞嘧啶的类似物。用取代的芳酰氯在吡啶中于56〜58℃进行芳基化。根据光谱数据，其他实验信息和从头算分子轨道计算，已经确定反应的中间体为2-芳基-5-氨基-1,2,4-噻二唑啉-3-酮（3）。。
• 1,2,4-Thiadiazolidine-3,5-dione
  申请人：ICN Pharmaceuticals, Inc.

  公开号：US04093624A1

  公开（公告）日：1978-06-06

  Compounds of the structure ##STR1## wherein Y is O, NH or NAc; X is H, .beta.-D-ribofuranosyl or 2,3,5-tri-O-Ac-.beta.-D-ribofuranosyl and Ac is acetyl; are useful as antimicrobal agent.

  结构式为##STR1##的化合物，其中Y为O、NH或NAc；X为H、β-D-核糖呋喃苷或2,3,5-三-O-乙酰基-β-D-核糖呋喃苷，Ac为乙酰基；可用作抗微生物剂。
• Synthetic and spectroscopic study of 5-amino-2-acyl-1,2,4-thiadiazolin-3-ones
  作者：Do Young Ra、Nam Sook Cho、Jung Hyun Moon、Sung Kwon Kang

  DOI：10.1002/jhet.5570350636

  日期：1998.11

  5-Amino-2-acyl-1,2,4-thiadiazolin-3-ones 2–1 can be synthesized from 5-amino-2H-1,2,4-thiadiazolin-3-one (1–1) via a selective acylation with an acid anhydride in pyridine. The 1H nmr spectral characteristics of 5-amino-2-acyl-1,2,4-thiadiazolin-3-ones 2–1 is in particular, compared with 5-amino-2H-1,2,4-thiadiazolin-3-one (1–1) and 5-amino-2-alkyl-1,2,4-thiadiazolin-3-ones 1–2, 1–3. The 5-amino group

  5-氨基-2-酰基-1,2,4-噻二唑啉-3-酮2-1可以由5-氨基-2-合成ħ -1,2,4-噻二唑啉-3-酮（1-1）经由在吡啶中用酸酐进行选择性酰化。在1个H核磁共振的5-氨基-2-酰基-1,2,4-噻二唑啉-3-酮的光谱特性2-1是尤其是与5-氨基-2-相比ħ -1,2,4- thiadiazolin- 3-one（1-1）和5-amino-2-烷基-1,2,4-噻二唑啉-3-ones 1-2，1-3。5-氨基2–1在其1 H nmr光谱中显示为两个峰，在较高温度下会合并为一个峰，而化合物1-1、1-2和1–3仅显示为一个峰。5-氨基-2-乙酰基-1,2,4-噻二唑啉-3-酮（2a-1）的C（5）-N（5）（在氨基）键的受限制旋转约为14.5 Kcal / mol 。
• Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives
  作者：Ana Castro、Arantxa Encinas、Carmen Gil、Stefan Bräse、Williams Porcal、Concepción Pérez、Francisco J. Moreno、Ana Martínez

  DOI：10.1016/j.bmc.2007.09.016

  日期：2008.1

  The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3 beta inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3 beta activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated. (c) 2007 Elsevier Ltd. All rights reserved.