3-p-Tolyl-hydantoin | 65119-75-7

• 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: 3-p-Tolyl-hydantoin
• 英文别名: 3-(4-Methylphenyl)imidazolidine-2,4-dione
• CAS: 65119-75-7
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: UKSSOJORPIHTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-p-Tolyl-hydantoin 在 盐酸 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design, synthesis and antiproliferative activities of diaryl urea derivatives bearing N-acylhydrazone moiety

  摘要：

  A new series of diaryl urea derivatives bearing N-acylhydrazone moiety were designed and synthesized. All the target compounds were evaluated for their antiproliferative activities against human leukemia cell line (HL-60), human lung adenocarcinoma epithelial cell line (A549) and human breast cancer cell line (MDA-MB-231) in vitro by standard MTT assay. The pharmacological results indicated that some compounds exhibited promising antitumor activities. Compound 1j showed the most potent antiproliferative activity against the tested three cell lines with IC50 values of 0.13 mu mol/L, 0.7 mu mol/L and 0.5 mu mol/L, respectively. (C) 2012 Ping Gong. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.06.009
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 氯乙酸 作用下， 生成 3-p-Tolyl-hydantoin
  参考文献：
  名称：

  Johnson; Pfau; Hodge, Journal of the American Chemical Society, 1912, vol. 34, p. 1046

  摘要：

  DOI：

文献信息

• Cu-catalyzed <i>N</i>-3-Arylation of Hydantoins Using Diaryliodonium Salts
  作者：Linn Neerbye Berntsen、Ainara Nova、David S. Wragg、Alexander H. Sandtorv

  DOI：10.1021/acs.orglett.0c00642

  日期：2020.4.3

  A general Cu-catalyzed, regioselective method for the N-3-arylation of hydantoins is described. The protocol utilizes aryl(trimethoxyphenyl)iodonium tosylate as the arylating agent in the presence of triethylamine and a catalytic amount of a simple Cu-salt. The method is compatible with structurally diverse hydantoins and operates well with neutral aryl groups or aryl groups bearing weakly donating/withdrawing

  描述了用于乙内酰脲的N -3-芳基化的一般的Cu催化的区域选择性方法。该方案在三乙胺和催化量的简单铜盐存在下，将甲苯磺酸芳基（三甲氧基苯基）碘鎓用作芳基化剂。该方法与结构上不同的乙内酰脲兼容，并且可以与中性芳基或带有弱供电子/吸出元素的芳基一起很好地操作。它也适用于药学上相关的乙内酰脲的快速多样化。
• Methods for treating Hepatitis C
  申请人：Karp Mitchell Gary

  公开号：US20080096928A9

  公开（公告）日：2008-04-24

  In accordance with the present invention, compounds that inhibit viral replication, preferably Hepatitis C Virus (HCV) replication, have been identified, and methods for their use provided. In one aspect of the invention, compounds useful in the treatment or prevention of a viral infection are provided. In another aspect of the invention, compounds useful in the treatment or prevention of HCV infection are provided.

  根据本发明，已经确定了抑制病毒复制的化合物，优选为丙型肝炎病毒（HCV）复制，同时提供了其使用方法。在本发明的一方面，提供了用于治疗或预防病毒感染的化合物。在本发明的另一方面，提供了用于治疗或预防HCV感染的化合物。
• METHODS FOR TREATING HEPATITIS C
  申请人：KARP Gary M.

  公开号：US20110268698A1

  公开（公告）日：2011-11-03

  The present invention provides compounds, pharmaceutical compositions, and methods of using such compounds or compositions for treating infection by a virus, or for affecting viral IBES activity.

  本发明提供了化合物、药物组合物以及使用这些化合物或组合物治疗病毒感染或影响病毒IBES活性的方法。
• CuF₂/MeOH-Catalyzed N³-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight
  作者：Tanumay Roy、Krishanu Mondal、Arunava Sengupta、Parthasarathi Das

  DOI：10.1021/acs.joc.3c00408

  日期：2023.5.5

  their role as a reactant and solvent, respectively. The proposed reaction mechanism indicated that selective N3-arylation of hydantoin is favorable in MeOH, which helps initiate the catalytic cycle by forming a square-planner Cu(II) complex where strong hydrogen-bond interactions are observed. This study is expected to improve the understanding of Cu(II)-catalyzed oxidative N-arylation reactions and for

  在 CuF 2 /MeOH 的辅助下，在室温和露天条件下，在无碱和无配体的条件下，建立了乙内酰脲与取代的芳基/杂芳基硼酸的有效且实用的 N-芳基化反应。该协议是通用的，各种 N-芳基化乙内酰脲以优异的产率和独特的区域选择性制备。进一步探索了CuF 2 /MeOH 组合以提供选择性 N 3-5-氟尿嘧啶核苷的芳基化。该协议的效率也通过市售药物 Nilutamide 的克级合成得到证明。基于密度泛函理论计算的机理研究表明，乙内酰脲和甲醇除了分别作为反应物和溶剂外，对于反应过程中催化活性铜物种的产生至关重要。所提出的反应机理表明选择性 N 3乙内酰脲的-芳基化在甲醇中是有利的，这有助于通过形成正方形规划的 Cu(II) 络合物来启动催化循环，在该络合物中观察到强氢键相互作用。这项研究有望提高对 Cu(II) 催化的氧化 N-芳基化反应的理解，并有助于从头设计和开发 Cu 催化的偶联反应。
• Process for preparing optically active hydantoins
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0175312A2

  公开（公告）日：1986-03-26

  A process for preparing optically active hydantoins having the general formula (II): wherein R' and R2, which are different from each other, are independently alkyl group aralkyl, group, aryl group, substituted alkyl group, substituted aralkyl group, or substituted aryl group, or R' and R2 form an asymmetric cyclic compound, characterized in that one configuration of racemic N-carbamoyl-a-amino acid having the general formula (I): wherein R' and R2 are as above, is enzymatically converted into the corresponding hydantoins. The present invention provides a process for an optical resolution with a high efficiency which can be used for the synthesis of (S)-6-fluoro-spiro- [chroman-4,4' -imidazolidine] -2',5'-dione (USAN; Sorbinil), which is an optically active hydantoins attracting public attention as a preventive or a remedy for the particular chronic symptoms of diabetes such as cataract and neuropathy, and (S)-a-methyl- 3,4-di- hydroxyphenylalanine (L-methyldopa), which is an optically active amino acid widely used as antihypertensives. Further, the present invention provides a novel finding that N-carbamoyl-a-amino acid having no hydrogen atom on its a-carbon atom can be biochemically converted into hydantoins by an enzymatic cyclization reaction.

  一种具有通式(II)的光学活性海因的制备方法： 其中R'和R2互不相同，独立地为烷基、芳基、取代的烷基、取代的芳基或取代的芳基，或R'和R2形成不对称环状化合物，其特征在于具有通式(I)的外消旋N-氨基甲酰基-a-氨基酸的一种构型： 其中 R' 和 R2 如上，通过酶法转化为相应的海因。 本发明提供了一种高效光学分解工艺，可用于合成(S)-6-氟-螺-[色满-4,4' -咪唑烷] -2',5'-二酮（USAN；(S)-a-甲基-3,4-二羟基苯丙氨酸(L-甲基多巴)，它是一种光学活性海因，作为白内障和神经病变等糖尿病特殊慢性症状的预防或治疗药物而备受公众关注；(S)-a-甲基-3,4-二羟基苯丙氨酸(L-甲基多巴)，它是一种光学活性氨基酸，被广泛用作抗高血压药物。此外，本发明还提供了一项新发现，即碳原子上没有氢原子的 N-氨基甲酰基-a-氨基酸可通过酶环化反应生化转化为 hydantoins。