4-氨基-1,3-噻唑-2(5H)-酮 | 19967-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 4-氨基-1,3-噻唑-2(5H)-酮
• 英文名称: 4-iminothiazolidin-2-one
• 英文别名: 4-Iminothiazolid-2-on；4-imino-1,3-thiazolidin-2-one
• CAS: 19967-65-8
• 化学式: C₃H₄N₂OS
• mdl: MFCD19159505
• 分子量: 116.144
• InChiKey: PECKLIXQHBFLKD-UHFFFAOYSA-N

物化性质

• 熔点：
  160-163 °C (decomp)
• 沸点：
  253.5±23.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  4-氨基-1,3-噻唑-2(5H)-酮 在 盐酸 作用下， 反应 0.25h， 生成 2,4-噻唑烷二酮
  参考文献：
  名称：

  Studies on azolidones and their derivatives

  摘要：

  DOI：

  10.1007/bf00755270
• 作为产物：
  描述：

  4-氨基-2-溴噻唑氢溴酸盐 在 水 作用下， 生成 4-氨基-1,3-噻唑-2(5H)-酮
  参考文献：
  名称：

  Polyfunctional Aliphatic Compounds. IV. The Cyclization of Nitriles by Halogen Acids. A New Synthesis of Thiazoles

  摘要：

  DOI：

  10.1021/jo01042a036

文献信息

• Synthesis and Evaluation of Anticancer Activity of 5-Ylidene-4- Aminothiazol-2(5H)-one Derivatives
  作者：Danylo Kaminskyy、Ivanna Subtel’na、Borys Zimenkovsky、Olexandr Karpenko、Andrzej Gzella、Roman Lesyk

  DOI：10.2174/1573406411666150211112049

  日期：2015.7.24

  The synthesis and antitumor activity screening of 4-aminothiazol-2(5H)-one derivatives were performed. The absence of possible 4-amino-imino tautomerism of thiazolidinones-2 has been confirmed based on the study of the molecule structures. The existence of the alone amino-form was confirmed. An anticancer activity screening was performed within the Developmental Therapeutics Program (National Cancer Institute/NIH, USA). Tested compounds possess low to moderate anticancer activity (average values - 60 cancer cell lines assay) with significant selective action on certain cancer cell lines (CCRF-CEM and RPMI-8226/leukemia, U251/CNS cancer, RFX 393/renal cancer, OVCAR/ovarian cancer etc.). The advantage of 5-ylidene-4-R-amino derivatives in comparison with compounds with free amino group was shown. Some structure-activity findings, the comparison of target compounds with isomeric 5-ylidene-2-imino(amino)thiazol-4(5H)-ones, as well as COMPARE analysis were described. Among the tested compounds (Z)-5-(furan-2-ylmethylidene)-4-(4-chlorophenylamino)thiazol-2(5H)-one (IIIk) and (Z)-5-(4-diethylaminophenylmethylidene)-4-(4-hydroxy-5-isopropyl-2-methylphenylamino)thiazol-2(5H)-one (IIIp) possessed the highest levels of activity.

  对4-氨基噻唑-2(5H)-酮衍生物的合成及抗肿瘤活性筛选进行了研究。基于对分子结构的研究，确认了噻唑啉酮-2中不存在可能的4-氨基-亚氨基互变异构体，确认了独立氨基型的存在。在国家癌症研究所/国家卫生研究院（美国）的开发疗法项目中进行了抗癌活性筛选。测试的化合物具有低到中等的抗癌活性（平均值 - 60个癌细胞系检测），对某些癌细胞系（如CCRF-CEM和RPMI-8226/白血病、U251/CNS癌、RFX 393/肾癌、OVCAR/卵巢癌等）表现出显著的选择性作用。相比于自由氨基团的化合物，5-烯基-4-R-氨基衍生物的优势得到了证明。文中还描述了一些结构-活性发现、目标化合物与异构体5-烯基-2-亚氨基（氨基）噻唑-4(5H)-酮的比较，以及COMPARE分析。在测试的化合物中，(Z)-5-(呋喃-2-基甲烯)-4-(4-氯苯基氨基)噻唑-2(5H)-酮 (IIIk) 和 (Z)-5-(4-二乙氨基苯基甲烯)-4-(4-羟基-5-异丙基-2-甲基苯基氨基)噻唑-2(5H)-酮 (IIIp) 展现了最高的活性水平。
• The application of anthraquinone-based triazenes as equivalents of diazonium salts in reaction with methylene active compounds
  作者：Andrii Lozynskyi、Oksana Sabadakh、Eugene Luchkevich、Tetyana Taras、Renata Vynnytska、Olexandr Karpenko、Volodymyr Novikov、Roman Lesyk

  DOI：10.1080/10426507.2018.1452236

  日期：2018.7.3

  GRAPHICAL ABSTRACT ABSTRACT A series of polyfunctionalized anthraquinonehydrazones have been prepared using azo-coupling reaction between anthraquinone-based triazenes and methylene active compounds in acetic acid without a catalyst. The structures of new synthesized compounds were confirmed by their IR, LCMS,1H and 13C NMR spectroscopic data. Some of the synthesized compounds were screened for their

  图形摘要 摘要 在没有催化剂的情况下，使用蒽醌基三氮烯和亚甲基活性化合物在乙酸中的偶氮偶联反应制备了一系列多官能化的蒽醌腙。新合成化合物的结构经IR、LCMS、1H和13C NMR光谱数据证实。根据美国 NCI 方案筛选了一些合成化合物的体外抗癌活性。生物筛选数据导致鉴定 1-N'-[3-(4-hydroxyphenyl)-4-oxo-2-thioxothiazolidin-5-ylidene]hydrazino}anthraquinone 3.4 对非小细胞肺具有抗肿瘤活性癌症 NCI-H460 (GP = 13.25%) 和结肠癌 HCT-116 (GP = 13.69%) 细胞系。
• Induction of Cyp450 enzymes by 4-thiazolidinone-based derivatives in 3T3-L1 cells in vitro
  作者：Konrad A. Szychowski、Bartosz Skóra、Anna Kryshchyshyn-Dylevych、Danylo Kaminskyy、Kamila Rybczyńska-Tkaczyk、Roman Lesyk、Jan Gmiński

  DOI：10.1007/s00210-020-02025-7

  日期：2021.5

  4-Thiazolidinones and related derivatives are regarded as privileged structures in medicinal chemistry and a source of new drug-like compounds. To date it is known that thiazolidinones are able to induce CYP1A1 activity in 3T3-L1 cells. Therefore, to extend the knowledge of the mechanism of thiazolidinones in the cell, four chemically synthesized heterocycles were tested on 3T3-L1 cells. The 3T3-L1 cells were exposed to Les-2194, Les-3640, Les-5935, and Les-6166. Our study showed that 1 μM βNF, Les-2194, and Les-6166 decreased the expression of Ahr mRNA. In turn, βNF, Les-2194, and Les-3640 increased the Cyp1a1 mRNA expression at the same time interval. On the other hand, Les-5935 was found to decrease the Cyp1a1 mRNA expression. Interestingly, the expression of Cyp1a2 mRNA was activated only by βNF and Les-2194. The expression of Cyp1b1 mRNA in the 3T3 cell line increased after the βNF and Les-2194 treatment but declined after the exposure to Les-5935 and Les-6166. Moreover, the Les-2194 and Les-5935 compounds were shown to increase the activity of EROD, MROD, and PROD. Les-3640 increased the activity of EROD and decreased the activity of PROD. In turn, the treatment with Les-6166 resulted in an increase in the activity of EROD and a decrease in the activity of MROD and PROD in the 3T3-L1 cells.

  摘要：4-噻唑烷酮及其相关衍生物被视为药物化学中的特权结构和新药物样化合物的来源。迄今为止已知噻唑烷酮能够诱导3T3-L1细胞中的CYP1A1活性。因此，为了扩展对细胞中噻唑烷酮机制的了解，对3T3-L1细胞进行了四种化学合成的杂环物质的测试。3T3-L1细胞暴露于Les-2194、Les-3640、Les-5935和Les-6166。我们的研究表明，1μM βNF、Les-2194和Les-6166降低了Ahr mRNA的表达。反过来，βNF、Les-2194和Les-3640在同一时间间隔内增加了Cyp1a1 mRNA的表达。另一方面，Les-5935被发现降低了Cyp1a1 mRNA的表达。有趣的是，只有βNF和Les-2194能激活Cyp1a2 mRNA的表达。3T3细胞系中Cyp1b1 mRNA的表达在βNF和Les-2194处理后增加，但在暴露于Les-5935和Les-6166后下降。此外，Les-2194和Les-5935化合物被证明增加了EROD、MROD和PROD的活性。Les-3640增加了EROD的活性并降低了PROD的活性。相反，Les-6166处理导致3T3-L1细胞中EROD活性增加，MROD和PROD活性下降。
• Synthesis and cytotoxicity of new thiazolo[4,5-b]pyridine-2(3H)-one derivatives based on α,β-unsaturated ketones and α-ketoacids
  作者：Andrii Lozynskyi、Borys Zimenkovsky、Lidia Radko、Sylwia Stypula-Trebas、Olexandra Roman、Andrzej K. Gzella、Roman Lesyk

  DOI：10.1007/s11696-017-0318-1

  日期：2018.3

  AbstractA series of thiazolo[4,5-b]pyridin-2(3H)-one derivatives were obtained via [3 + 3]-cyclization of 4-amino-5H-thiazol-2-one and α,β-unsaturated ketones or α-ketoacids. The structures of newly synthesized compounds were established by spectral data and a single-crystal X-ray diffraction analysis. Target compounds were screened for their anticancer activity according to US NCI protocols and moderate

  摘要通过4-氨基-5 H-噻唑-2-酮和α，β-不饱和的[3 + 3]-环化获得一系列噻唑并[4,5- b ]吡啶-2（3 H）-one衍生物酮或α-酮酸。通过光谱数据和单晶X射线衍射分析来建立新合成的化合物的结构。根据US NCI方案筛选目标化合物的抗癌活性，并确认了对测试细胞系的中等抑制活性。5-苯基-7-（吡啶-3-基）-3 H-噻唑并[4,5 - b ]吡啶-2-一（3）和2-氧代-7-噻吩-2-基-2,3-二氢噻唑并[4,5 - b ]吡啶-5-羧酸（12筛选了它们对HepG2和Balb / c 3T3细胞的细胞毒性作用，使用MTT，NRU和TPC分析显示了令人鼓舞的结果。 图形概要
• One-Pot Synthesis of 5-Ene-4-aminothiazol-2(5H)-ones and Chromeno[2,3-d]thiazol-2-ones
  作者：Roman Lesyk、Danylo Kaminskyy、Ivanna Subtel’na、Andriy Pyrih、Danylo Shtoyko、Anna Susel、Andrzej Gzella

  DOI：10.1055/s-0036-1588687

  日期：——

  5-arylidene-4-aminothiazol-2(5H)-ones based on the reaction of isorhodanine, aromatic aldehydes, and ethanolamine. The one-pot procedure for chromeno[2,3-d]thiazol-2-one synthesis starting from 4-aminothiazol-2(5H)-one was proposed following the study of 5-(2-hydroxybenzylidene)-thiazolidinones. Structural features of the starting 4-thioxo-2-thiazolidinone, 4-aminothiazol-2(5H)-one, and target compounds are

  在此，我们描述了一种基于异罗丹宁、芳香醛和乙醇胺反应的 5-亚芳基-4-氨基噻唑-2(5H)-酮的一锅三组分合成方法。在对 5-(2-羟基亚苄基)-噻唑烷酮的研究之后，提出了从 4-氨基噻唑-2(5H)-one 开始合成 chromeno[2,3-d]thiazol-2-one 的一锅法。讨论了起始 4-thioxo-2-thiazolidinone、4-aminothiazol-2(5H)-one 和目标化合物的结构特征。