5-amino-5-ethyl-1-phenylbarbituric acid | 221679-70-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-amino-5-ethyl-1-phenylbarbituric acid
• 英文别名: 5-amino-5-ethyl-1-phenyl-1,3-diazinane-2,4,6-trione
• CAS: 221679-70-5
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: LCDGHJAOXXIZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-5-ethyl-1-phenylbarbituric acid 在 sodium ethanolate 作用下， 反应 3.0h， 以70%的产率得到5-ethyl-5-phenylcarbamoylhydantoin
  参考文献：
  名称：

  Guetschow, Michael; Hecker, Thomas; Eger, Kurt, Synthesis, 1999, # 3, p. 410 - 414

  摘要：

  DOI：
• 作为产物：
  描述：

  5-Azido-5-aethyl-1-phenylbarbitursaeure 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以67%的产率得到5-amino-5-ethyl-1-phenylbarbituric acid
  参考文献：
  名称：

  Guetschow, Michael; Hecker, Thomas; Eger, Kurt, Synthesis, 1999, # 3, p. 410 - 414

  摘要：

  DOI：

文献信息

• Preparation of phthalamic acid derivatives and ring closure to phthalimidobarbituric acids
  作者：Agnieszka Ambrożk、Michael Gütschow

  DOI：10.1002/jhet.5570440606

  日期：2007.11

  Phthalamic acid derivatives with a barbiturate moiety were prepared from 5-amino-5-ethylbarbituric acids. To circumvent an undesired acetylation in glacial acetic acid during the preparation of phthalimidobarbituric acids, two routes were proven exemplarily. On the one hand, a phthalamic acid (6a) was isolated and subsequently cyclized with acetic anhydride to the corresponding phthalimide 2a. On the

  由5-氨基-5-乙基巴比妥酸制备具有巴比妥酸酯部分的邻氨基苯甲酸衍生物。为了避免在邻苯二甲酰亚胺巴比妥酸的制备过程中在冰醋酸中发生不希望的乙酰化，示例性地证明了两种途径。一方面，分离邻苯二甲酸（6a），随后用乙酸酐环化成相应的邻苯二甲酰亚胺2a。另一方面，依次用三氟乙酸和三氟乙酸酐处理邻苯二甲酸叔丁酯（5b），以实现与邻苯二甲酰亚胺2b的杂环化。这些路线可能对制备衍生自空间受阻伯胺的其他邻苯二甲酰亚胺有用。
• Synthesis and Antiangiogenic Properties of Tetrafluorophthalimido and Tetrafluorobenzamido Barbituric Acids
  作者：Agnieszka Ambrożak、Christian Steinebach、Erin R. Gardner、Shaunna L. Beedie、Gregor Schnakenburg、William D. Figg、Michael Gütschow

  DOI：10.1002/cmdc.201600496

  日期：2016.12.6

  two decades. Herein we report the design and synthesis of three chemotypes of barbituric acids derived from the thalidomide structure: phthalimido‐, tetrafluorophthalimido‐, and tetrafluorobenzamidobarbituric acids. The latter were obtained by a new tandem reaction, including a ring opening and a decarboxylation of the fluorine‐activated phthalamic acid intermediates. Thirty compounds of the three

  在过去的二十年中，新型沙利度胺衍生物作为免疫调节剂和抗血管生成剂的开发得以恢复。在本文中，我们报道了从沙利度胺结构衍生的三种巴比妥酸的化学型的设计和合成：邻苯二甲酰亚胺，四氟邻苯二甲酰亚胺和四氟苯甲酰胺基巴比妥酸。后者是通过新的串联反应获得的，包括开环和氟活化的邻苯二甲酸酯中间体的脱羧。通过测量大鼠主动脉环外植体中微血管生长的减少，在离体测定中评估了三种化学型的30种化合物的抗血管生成特性。四氟邻苯二甲酰亚胺基巴比妥酸中邻苯二甲酰亚胺基团的四氟化是必不可少的，因为所有未氟化的对应物都失去了抗血管生成活性。在相应的四氟苯甲酰胺基巴比妥酸的情况下，五元环的打开以及随之而来的构象自由度的提高是可以很好地耐受的。比较X射线晶体学分析表明，尽管它们的分子结构在扭转挠性和可能的​​氢键网络方面有所不同，但它们的活性得以保留。
• Analogs of thalidomide as potential angiogenesis inhibitors
  申请人：——

  公开号：US20040077685A1

  公开（公告）日：2004-04-22

  A number of thalidomide metabolites having superior anti-angiogenic properties have now been isolated and identified In addition, thalidomide analogs that mimic the effects of the isolated and identified active thalidomide metabolites, and variations of such thalidomide analogs, have been developed. Such thalidomide analog compounds show enhanced potency in the inhibition of undesirable angiogenesis without the undesirable effects of administration of thalidomide.

  现在已经分离和鉴定出了多种具有优越的抗血管生成作用的沙利度胺代谢产物。此外，已经开发出了模仿这些活性沙利度胺代谢产物效果的沙利度胺类似物和这些沙利度胺类似物的变体。这些沙利度胺类似物化合物在抑制不良血管生成方面显示出增强的效力，而没有沙利度胺的不良影响。
• Tetrahalogenated compounds useful as inhibitors of angiogenesis
  申请人：The United States of America as represented by the Secretary of the Department of Health and Human Services

  公开号：US08143252B2

  公开（公告）日：2012-03-27

  Methods for inhibiting a neoplasm in a subject and methods of inhibiting undesired angiogenesis that include administering to a subject a therapeutically effective amount of at least one novel tetrahalogenated compound, or a pharmaceutically acceptable salt thereof.

  抑制患者体内肿瘤和抑制不必要血管生成的方法，包括向患者施加至少一种新型四卤代化合物或其药学上可接受的盐的治疗有效剂量。
• Aza analogues of thalidomide
  作者：Michael Gütschow、Thomas Hecker、Andrea Thiele、Sunna Hauschildt、Kurt Eger

  DOI：10.1016/s0968-0896(00)00323-0

  日期：2001.4

  A synthetic entry to derivatives of the new classes of 5-phthalimidouracils and 5-phthalimidobarbituric acids is reported. These 5-phthalimidopyrimidines as well as phthalimido-2.4-difluorobenzenes were designed as analogues of thalidomide. a we ii known inhibitor of TNF-alpha production. A preliminary in vitro investigation of the compounds as inhibitors of, the TNF-alpha production was performed. Among the compounds of the present series, 5-ethyl-1-phenyl-5-(tetrafluorophthalimido)barbituric acid and 2-(2.4-difluorophenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione were proved to be potent inhibitors. Both compounds showed inhibitory activity in the lower micromolar range on the LPS-induced TNF-alpha production in human monocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.