(Z)-3'-deimino-2',4'-bis(demethyl)-4'-phenyl-3'-thioxoaplysinopsin | 317384-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-3'-deimino-2',4'-bis(demethyl)-4'-phenyl-3'-thioxoaplysinopsin
• 英文别名: (Z)-5-((1H-indol-3-yl)methylene)-3-phenyl-2-thioxoimidazolidin-4-one；(Z)-5-[(1H-indol-3-yl)methylidene]-3-phenyl-2-thioxoimidazolidin-4-one；(5Z)-5-(1H-indol-3-ylmethylidene)-3-phenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 317384-07-9
• 化学式: C₁₈H₁₃N₃OS
• 分子量: 319.387
• InChiKey: LPUMASDYXGPFNI-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.13
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-3'-deimino-2',4'-bis(demethyl)-4'-phenyl-3'-thioxoaplysinopsin 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  A CONVENIENT SYNTHESIS OF GLYCOSYLATED HYDANTOINS AS POTENTIAL ANTIVIRAL AGENTS

  摘要：

  Reaction of 5-arylidene-2-thiohydantoins 3a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. Deacetylation with ammonia in methanol caused a change of the S-glycosyl residue and gave the N-3 glycosylated analogues 7a-h. S-Glycosylation also occured when N-3 substituted hydantoins 9a-h were reacted.

  DOI：

  10.1080/10426509708043491
• 作为产物：
  描述：

  methyl 2-{[2-acetyl-2-(benzyloxycarbonyl)ethenyl]amino}-3-(1H-indol-3-yl)prop-2-enoate 在 一水合肼 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 10.0h， 生成 (Z)-3'-deimino-2',4'-bis(demethyl)-4'-phenyl-3'-thioxoaplysinopsin
  参考文献：
  名称：

  摘要：

  Simple and stereoselective syntheses of aplysinopsins and their analogs from either methyl 2-[(2,2 disubstituted ethenyl)amino]-3-(dimethylamino)prop-2-enoates or 5-[(dimethylamino)methylidene]imidazolidine-2,4-diones 20 are described. The structures of products are established by H-1 and C-13-NMR. and NOESY spectroscopy, and X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(20001004)83:10<2802::aid-hlca2802>3.0.co;2-9

文献信息

• Design, synthesis, characterization, molecular docking and computational studies of 3-phenyl-2-thioxoimidazolidin-4-one derivatives
  作者：U. Vanitha、R. Elancheran、V. Manikandan、S. Kabilan、K. Krishnasamy

  DOI：10.1016/j.molstruc.2021.131212

  日期：2021.12

  3-phenyl-2-thioxoimidazolidin-4-one derivatives were synthesized and thoroughly characterized by FT-IR, 1H NMR, 13C NMR spectroscopic techniques. The structures of the compounds (5a-c) were further confirmed by single-crystal XRD analysis. Molecular docking studies were utilized to foresee the binding interactions of 3-phenyl-2-thioxoimidazolidin-4-one derivatives with the Estrogen Receptor (3ERT) and

  乳腺癌是女性中最广为人知的侵入性疾病，也是全球癌症死亡的第二大原因。硫代乙内酰脲具有广泛而有趣的药理特性，如抗肿瘤药、抗惊厥药、抗抑郁药、抗病毒、抗血栓形成活性等。合成了 3-苯基-2-硫代咪唑啉-4-酮衍生物，并通过 FT-IR、1 H NMR、13 C NMR光谱技术。化合物的结构（5a-c) 通过单晶 XRD 分析进一步证实。分子对接研究被用来预测 3-phenyl-2-thioxoimidazolidin-4-one 衍生物与雌激素受体 (3ERT) 的结合相互作用，并评估它们的 ADME 特性以寻找先导化合物。受体-配体对接研究使用薛定谔软件进行。诸如密度泛函理论和 Hirshfeld 表面分析之类的计算研究被用来识别化合物的电子状态和分子参数 ( 5a-c )。此外，这些化合物的体外和体内抗癌活性将在未来进行评估。
• ——
  作者：Lovro Selič、Renata Jakše、Kristina Lampič、Ljubo Golič、Simona Golič-Grdadolnik、Branko Stanovnik

  DOI：10.1002/1522-2675(20001004)83:10<2802::aid-hlca2802>3.0.co;2-9

  日期：2000.10.4

  Simple and stereoselective syntheses of aplysinopsins and their analogs from either methyl 2-[(2,2 disubstituted ethenyl)amino]-3-(dimethylamino)prop-2-enoates or 5-[(dimethylamino)methylidene]imidazolidine-2,4-diones 20 are described. The structures of products are established by H-1 and C-13-NMR. and NOESY spectroscopy, and X-ray crystal-structure analysis.
• A CONVENIENT SYNTHESIS OF GLYCOSYLATED HYDANTOINS AS POTENTIAL ANTIVIRAL AGENTS
  作者：Ahmed I. Khodair

  DOI：10.1080/10426509708043491

  日期：1997.3.1

  Reaction of 5-arylidene-2-thiohydantoins 3a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. Deacetylation with ammonia in methanol caused a change of the S-glycosyl residue and gave the N-3 glycosylated analogues 7a-h. S-Glycosylation also occured when N-3 substituted hydantoins 9a-h were reacted.