(5Z)-5-亚乙基-2,4-咪唑烷二酮 | 137920-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (5Z)-5-亚乙基-2,4-咪唑烷二酮
• 英文名称: (Z)-5-ethylidenehydantoin
• 英文别名: 5-Ethyliden-hydantoin；(Z)-5-Ethylideneimidazolidine-2,4-dione；(5Z)-5-ethylideneimidazolidine-2,4-dione
• CAS: 137920-51-5
• 化学式: C₅H₆N₂O₂
• 分子量: 126.115
• InChiKey: UGIOACMSGGVRIA-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5Z)-5-亚乙基-2,4-咪唑烷二酮 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 (Z)-1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-ethylidene-2,4-imidazolidinedione
  参考文献：
  名称：

  AZT 的乙内酰脲类似物的合成和抗病毒评价

  摘要：

  3'-叠氮核苷 4 是通过甲硅烷基化的 (Z)-5-亚乙基乙内酰脲和 (Z)-5-亚苄基乙内酰脲与甲基 3-叠氮基-5-O-叔丁基二苯基甲硅烷基-2,3-D-二乙氧基乙内酰脲缩合合成的五呋喃糖苷 (3)。核苷4在用四丁基氟化铵处理时解封闭。在核苷合成过程中，亚乙基从 Z 构型异构化为 E 构型。新的核苷对 HIV-1 或 HSV-1 没有表现出任何明显的活性。

  DOI：

  10.1002/ardp.19943271010
• 作为产物：
  描述：

  5-ethylidene-2-thioxoimidazolidin-4-one 在 氯乙酸 作用下， 生成 (5Z)-5-亚乙基-2,4-咪唑烷二酮
  参考文献：
  名称：

  Hydantoin analogs of thymidine

  摘要：

  Hydantoin nucleosides were synthesized from a protected methyl 2-deoXy-D-ribofuranoside in a Friedel-Crafts catalyzed silyl-Hilbert-Johnson reaction as modified by Vorbruggen. Atypical byproducts are accounted for by assuming the initial step being a ring opening of the sugar to give an acyclic glycos-1-yl cation.

  DOI：

  10.1021/jo00074a028

文献信息

• Thiohydantoins and hydantoins derived from amino acids as potent urease inhibitors: Inhibitory activity and ligand-target interactions
  作者：Priscila Goes Camargo、Marciéli Fabris、Matheus Yoshimitsu Tatsuta Nakamae、Breno Germano de Freitas Oliveira、Camilo Henrique da Silva Lima、Ângelo de Fátima、Marcelle de Lima Ferreira Bispo、Fernando Macedo

  DOI：10.1016/j.cbi.2022.110045

  日期：2022.9

  report the investigation of hydantoins and thiohydantoins derived from L and d-amino acids as inhibitors against the Canavalia ensiformis urease (CEU). The biochemical in vitro assay against CEU revealed a promising inhibitory potential for most thiohydantoins with six of them showing %I higher than the reference inhibitor thiourea (56.5%). In addition, thiohydantoin derived from l-valine, 1b, as well as

  我们报告了从L和d氨基酸中提取的乙内酰脲和硫代乙内酰脲作为抗Canavalia ensiformis脲酶 (CEU) 抑制剂的研究。针对 CEU的体外生化试验显示，大多数硫代乙内酰脲具有良好的抑制潜力，其中 6 种显示 %I 高于参考抑制剂硫脲 (56.5%)。此外，衍生自l-缬氨酸的硫代乙内酰脲1b以及衍生自l的乙内酰脲2d-甲硫氨酸被确定为最有效的抑制剂，%I 分别为 90.5 和 85.9。酶动力学研究证明了这些化合物的混合和非竞争性抑制曲线，1b的 K i值为 0.42 mM ， 2d的 K i 值为0.99 mM 。这些从传统比色法获得的动力学参数与 K D严格相关通过脲酶复合物的饱和转移差 (STD) 技术光谱测量的值。STD 也用于证明负责与酶结合的配体部分。分子对接研究表明，硫代乙内酰脲和乙内酰脲环可以作为药效团，因为它们通过氢键相互作用与酶活性和/或变构位点中的关键氨基酸
• Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright

  DOI：10.1021/jo00024a036

  日期：1991.11

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.
• Pinner; Lifschuetz, Chemische Berichte, 1887, vol. 20, p. 2353
  作者：Pinner、Lifschuetz

  DOI：——

  日期：——
• Abdel-Bary, Hamed M.; El-Barbary, Ahmed A.; Khodair, Ahmed I., Bulletin de la Societe Chimique de France, 1995, vol. 132, # 2, p. 149 - 155
  作者：Abdel-Bary, Hamed M.、El-Barbary, Ahmed A.、Khodair, Ahmed I.、Megied, Ahmed Es Abdel、Pedersen, Erik B.、Nielsen, Claus

  DOI：——

  日期：——