3-乙基-2-硫代乙内酰脲 | 32607-37-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-乙基-2-硫代乙内酰脲
• 英文名称: 3-ethyl-2-thioxo-imidazolidin-4-one
• 英文别名: 3-ethyl-2-thiohydantoin；3-Aethyl-2-thioxo-imidazolidin-4-on；3-ethyl-2-thioxoimidazolidin-4-one；3-Aethyl-2-thiohydantoin；3-ethyl-2-sulfanylideneimidazolidin-4-one
• CAS: 32607-37-7
• 化学式: C₅H₈N₂OS
• mdl: MFCD01327206
• 分子量: 144.197
• InChiKey: PNLZPZBAVUHFCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-乙基-2-硫代乙内酰脲 在 氢溴酸 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成 3-ethyl-5-[(Z)-(2-methyl-1H-indol-3-yl)methylidene]-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  通过五元杂环的N，N-（二甲基氨基）亚甲基衍生物中的二甲胺取代简单合成apssinopsin类似物

  摘要：

  通过将N，N-（二甲基氨基）亚甲基取代的乙内酰脲，硫代乙内酰脲和噻唑酮衍生物与吲哚衍生物简单偶联，制备了一些新的皂素类似物。基于远距离异核偶联常数，使用2D HMBC相关技术确定了环外CC双键周围的构型。

  DOI：

  10.1016/s0040-4020(01)00838-9
• 作为产物：
  描述：

  N-(乙基硫代氨基甲酰)甘氨酸 在 硫酸 作用下， 以 丙酮 为溶剂， 生成 3-乙基-2-硫代乙内酰脲
  参考文献：
  名称：

  Inhibition of Cancer-Associated Mutant Isocitrate Dehydrogenases by 2-Thiohydantoin Compounds

  摘要：

  Somatic mutations of isocitrate dehydrogenase 1 (LDH1) at R132 are frequently found in certain cancers such as glioma. With losing the activity of wild-type IDH1, the R132H and R132C mutant proteins can reduce alpha-ketoglutaric acid (alpha-KG) to D-2-hydroxyglutaric acid (D2HG). The resulting high concentration of D2HG inhibits many alpha-KG-dependent dioxygenases, including histone demethylases, to cause broad histone hypermethylation. These aberrant epigenetic changes are responsible for the initiation of these cancers. We report the synthesis, structure activity relationships, enzyme kinetics, and binding thermodynamics of a novel series of 2-thiohydantoin and related compounds, among which several compounds are potent inhibitors of mutant IDH1 with K-i as low as 420 nM. X-ray crystal structures of IDH1(R132H) in complex with two inhibitors are reported, showing their inhibitor-protein interactions. These compounds can decrease the cellular concentration of D2HG, reduce the levels of histone methylation, and suppress the proliferation of stem-like cancer cells in BT142 glioma with IDH1 R132H mutation.

  DOI：

  10.1021/acs.jmedchem.5b00684

文献信息

• One-pot synthesis, theoretical study and antimicrobial activity of 5,5′-(1,4-phenylenebis-(methanylylidene))Bis(3-Aryl(Alkyl)-2-thioxoimidazolidin-4-one) derivatives
  作者：Raafat M. Shaker、Hisham A. Abd El-Naby、Essam Kh. Ahmed、Mahmoud A. A. Ibrahim、Sageda A. Gedamy

  DOI：10.1080/10426507.2018.1528256

  日期：2019.2.1

  Abstract A simple, facile, and convenient practical method for the one-pot synthesis of pharmaceutically interesting 5,5`-(1,4-phenylenebis-(methanylylidene))bis-thiohydantoins via a three-component condensation reaction of terephthalaldehyde, α-amino acids and isothiocyanates had been developed. The S-alkylated derivatives 6a and 6b were obtained by the alkylation of the bis-thiohydantoins 4a with

  摘要 通过对苯二醛、α-的三组分缩合反应，一锅合成具有药学意义的 5,5`-(1,4-亚苯基双-(亚甲基亚基))双-硫代乙内酰脲的简单、简便、实用的方法。已开发出氨基酸和异硫氰酸酯。S-烷基化衍生物6a和6b通过在碱性介质中用甲基碘和/或苄基氯对双硫代乙内酰脲4a进行烷基化而获得。合成化合物的分子结构通过元素分析和光谱数据（IR、1H、13C NMR和MS）得到证实。通过 B3LYP/6-31+G* 水平的 DFT 计算研究了更稳定的 Z-或 E-异构体作为 4a、6a 和 8a 的主要形式。筛选了一些制备的化合物的体外抗微生物活性。化合物 4a、6b、图8b和8c对革兰氏阳性菌蜡样芽孢杆菌表现出低抗菌活性。(5Z,5'Z)-5,5'-(1,4-Phenylenebis(methanylylidene))bis(3-benzyl-2-thioxoimidazolidin-4-one) (4b)
• Synthesis and Transformations of Ethyl 3-Formyl-1H-indole-2-carboxylate. Preparation of Aplysinopsin and β-Carboline Thiohydantoin Analogues
  作者：Renata Jakše、David Bevk、Amalija Golobič、Jurij Svete、Branko Stanovnik

  DOI：10.1515/znb-2006-0407

  日期：2006.4.1

  Various aplysinopsin and β -carboline thiohydantoin analogues were prepared starting from ethyl 3-formyl-1H-indole-2-carboxylate by condensation with the active methylene group of 2-thiohydantoin, rhodanine, or thiobarbituric acid derivatives

  各种aplysinopsin和β-咔啉硫代异噁唑酮类似物是从乙酸乙酯3-甲醛基-1H-吲哚-2-羧酸酯开始制备的，通过与2-咔啉硫代异噁唑酮、罗丹宁或硫代咪唑酮衍生物的活性亚甲基基团进行缩合反应制备。
• Broad Spectrum Antiviral and Antiparasitic Agents
  申请人：Lee Benhur

  公开号：US20130028966A1

  公开（公告）日：2013-01-31

  The invention provides compounds represented by the formulae: (I) and (II) where the compounds are useful in treating, for example, viral and/or parasitic infections. Also provided are pharmaceutical compositions comprising the compounds and methods of treatment using the compounds.

  本发明提供了公式（I）和（II）所代表的化合物，这些化合物可用于治疗病毒和/或寄生虫感染等疾病。本发明还提供了包含这些化合物的制药组合物以及使用这些化合物进行治疗的方法。
• Broad spectrum antiviral and antiparasitic agents
  申请人：Lee Benhur

  公开号：US09139575B2

  公开（公告）日：2015-09-22

  The invention provides compounds represented by the formulae: (I) and (II) where the compounds are useful in treating, for example, viral and/or parasitic infections. Also provided are pharmaceutical compositions comprising the compounds and methods of treatment using the compounds.

  本发明提供的化合物由公式（I）和（II）表示，其中这些化合物在治疗例如病毒和/或寄生虫感染方面非常有用。此外还提供包含这些化合物的药物组合物以及使用这些化合物的治疗方法。
• BROAD SPECTRUM ANTIVIRAL AND ANTIPARASITIC AGENTS
  申请人：The Regents of the University of California

  公开号：US20160207908A1

  公开（公告）日：2016-07-21

  The invention provides compounds represented by the formulae: (I) and (II) where the compounds are useful in treating, for example, viral and/or parasitic infections. Also provided are pharmaceutical compositions comprising the compounds and methods of treatment using the compounds.

  该发明提供了由公式（I）和（II）表示的化合物，这些化合物在治疗例如病毒性和/或寄生虫感染方面非常有用。还提供了包含这些化合物的药物组合物以及使用这些化合物的治疗方法。