5-(4-dimethylaminobenzylidene)imidazolidine-2,4-dione | 10040-87-6

• 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: 5-(4-dimethylaminobenzylidene)imidazolidine-2,4-dione
• 英文别名: 5-(4-dimethylamino-benzylidene)-imidazolidine-2,4-dione；5-(4-Dimethylamino-benzyliden)-hydantoin；5-[[4-(Dimethylamino)phenyl]methylidene]imidazolidine-2,4-dione
• CAS: 10040-87-6
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: KLVRHZIOWMWJOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-dimethylaminobenzylidene)imidazolidine-2,4-dione 在 镍 氢氧化钾 、 氢气 作用下， 反应 28.0h， 以50%的产率得到5-(4-dimethylaminobenzyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  5-（4-二甲基氨基苄基）咪唑烷-2,4-二酮的合成及抗抑郁活性

  摘要：

  通过催化氢化相应的亚苄基化合物来制备5-（4-二甲基氨基苄基）咪唑烷-2，4-二酮。在小鼠中进行的抗抑郁试验表明，其对丁苯那嗪诱导的上睑下垂和左旋多巴诱导的行为改变的增强作用的ED50值分别为42和17 mg / kg po。体外神经化学研究表明，该化合物不会抑制选定的生物胺进入小鼠全脑的粗突触体中，并且在体内和体外均不具有明显的单胺氧化酶抑制活性。因此，该化合物具有潜在的抗抑郁活性，其机制不同于三环抗抑郁药和单胺氧化酶抑制剂。

  DOI：

  10.1002/jps.2600690933
• 作为产物：
  描述：

  海因 、 对二甲氨基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 5-(4-dimethylaminobenzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  已知岩藻糖苷酶抑制剂的生物电子等排修饰发现α-的新颖抑制剂升-fucosidase †

  摘要：

  已知岩藻糖苷酶抑制剂A和B的生物立体异构修饰产生了三种新类型的分子，分别属于呋喃吡啶二酮，硫代乙内酰脲和乙内酰脲化学分型的4b，5c和6a，它们可能与α- L-岩藻糖苷酶（牛肾来源）结合。分子对接揭示并比较了4b，5c和6a与A和B之间的假定结合相互作用与α- L同源模型的活性位点-岩藻糖苷酶。基于此初步研究，设计和合成了基于呋喃吡啶二酮，硫代乙内酰脲和乙内酰脲的小分子文库，然后对其体外筛选抗α- L-岩藻糖苷酶（牛肾来源）产生了一种有效的IC抑制剂（化合物4e）约0.7μM中的50。当针对健康的哺乳动物COS-1细胞进行测试时，化合物4e不具有细胞毒性。反应动力学研究表明它是一种混合抑制剂。最后化合物4a，b，e和f带有呋喃并吡啶二酮基序的α，也显示出对MCF 7乳腺癌细胞增殖的实质性抑制。

  DOI：

  10.1039/c6ra24939f

文献信息

• 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.
• Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives
  作者：Danylo Kaminskyy、Borys Zimenkovsky、Roman Lesyk

  DOI：10.1016/j.ejmech.2009.02.023

  日期：2009.9

  The synthesis and evaluation of anticancer activity of 2,4-thia(imida)zolidinedione-3- and 5-acetic acids amides were described. The structures of compounds were determined by IR, H-1 NMR, and MS analysis. In vitro anticancer activity of these compounds has been tested in National Cancer Institute (NCI) and the relationships between structure and anticancer activity are discussed. Among 2,4-azolidinedione-acetic acids derivatives 2-[5-(4-chlorobenzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide (Ic) was superior to other related compounds in terms of high selectivity for the leukemia CCRF-CEM (log GI(50) = -6.06), HL-60(TB) (log GI(50) = -6.53), MOLT-4 (log GI(50) = -6.52) and SR (log GI(50) -6.51) cell lines. (C) 2009 Elsevier Masson SAS. All rights reserved.