m-tolylhydantoin | 71532-35-9

• 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: m-tolylhydantoin
• 英文别名: 3-(3-methylphenyl)hydantoin；3-m-tolyl-imidazolidine-2,4-dione；3-m-Tolyl-imidazolidin-2,4-dion；3-(3-tolyl)-hydantoin；3-(3-Methylphenyl)imidazolidine-2,4-dione
• CAS: 71532-35-9
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: XZTSVSOCDJDQCR-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C(Solv: methanol (67-56-1))
• 密度：
  1.274±0.06 g/cm3(Predicted)

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：

  m-tolylhydantoin 、 对羟基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 (5Z)-5-[(4-hydroxyphenyl)methylidene]-3-(3-methylphenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Structural optimization of non-nucleoside DNA methyltransferase inhibitor as anti-cancer agent

  摘要：

  Inhibition of DNA methyltransferase 1 (DNMT1) can reverse the malignant behavior of cancer cells by restoring expression of aberrantly silenced genes that are required for differentiation, senescence, and apoptosis. Clinically used DNMT1 inhibitors decitabine and azacitidine inhibit their target by covalent trapping after incorporation into DNA as azacytidine analogs. These nucleoside compounds are prone to rapid enzymatic inactivation in blood, posing challenges to the development of purely epigenetic dosing schedules. Non-nucleoside compounds that suppress expression or function of DNMT1 may overcome this problem. Using a high-throughput PCR-based site specific chromatin condensation assay, we identified a compound that reactivated Cyclin-Dependent Kinase Inhibitor 2A (CDKN2A) in myeloma cells and suppressed expression of DNMT1 from a library of 5120 chemically diverse small molecules. Lead optimization was performed to generate 26 new analogs with lung cancer proliferation and DNMT1 expression as activity readout. Two of the new derivatives showed 2 fold improvement of growth inhibiting potency and also decreased DNMT1 protein levels in lung cancer cells. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2016.01.020
• 作为产物：
  描述：

  2-amino-N-(m-tolyl)acetamide 在 氢氧化钾 、 sodium hydroxide 、 苯 作用下， 生成 m-tolylhydantoin
  参考文献：
  名称：

  Hill; Kelsey, Journal of the American Chemical Society, 1922, vol. 44, p. 2363

  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。
• Cegan, Alexandr; Vecera, Miroslav, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 6, p. 1521 - 1528
  作者：Cegan, Alexandr、Vecera, Miroslav

  DOI：——

  日期：——
• Ryczek, J., Polish Journal of Chemistry, 1994, vol. 68, # 12, p. 2599 - 2604
  作者：Ryczek, J.

  DOI：——

  日期：——
• Suk-Choong Kim; Byoung-Mog Kwon, Synthesis, 1982, # 9, p. 795 - 796
  作者：Suk-Choong Kim、Byoung-Mog Kwon

  DOI：——

  日期：——
• KIM, SUK-CHOONG;KWON, BYOUNG-MOG, SYNTHESIS, BRD, 1982, N 9, 795-796
  作者：KIM, SUK-CHOONG、KWON, BYOUNG-MOG

  DOI：——

  日期：——