4-乙基氨基脲 | 13050-41-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-乙基氨基脲
• 英文名称: 4-ethylsemicarbazide
• 英文别名: ethylurea hydrazide；4-ethyl semicarbazide；Kohlensaeure-aethylamid-hydrazid；4-Aethyl-semicarbazid；1-Amino-3-ethylurea
• CAS: 13050-41-4
• 化学式: C₃H₉N₃O
• mdl: MFCD11212739
• 分子量: 103.124
• InChiKey: CJYIAZYTBJVFOT-UHFFFAOYSA-N

物化性质

• 熔点：
  <100 °C
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-乙基氨基脲 、 苯甲醛 生成 Benzaldehyd-4-ethylsemicarbazon
  参考文献：
  名称：

  Ohme,R.; Preuschhof,H., Journal fur praktische Chemie (Leipzig 1954), 1971, vol. 313, p. 626 - 635

  摘要：

  DOI：
• 作为产物：
  描述：

  异氰酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 以461 mg (78%)的产率得到4-乙基氨基脲
  参考文献：
  名称：

  Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof

  摘要：

  这项发明涉及由式I表示的含有碳环和杂环取代的半卡巴松和硫代半卡巴松： 1 或其药学上可接受的盐或前药，其中： Y为氧或硫；R 1 ，R 21 ，R 22 和R 23 独立地为氢，烷基，环烷基，烯基，炔基，卤代烷基，芳基，氨基烷基，羟基烷基，烷氧基烷基或羧基烷基；或R 22 和R 23 ，与N一起形成一个杂环；A 1 和A 2 独立地为芳基，杂芳基，饱和或部分不饱和的碳环或饱和或部分不饱和的杂环，其中任何一个可选择地被取代；X为O、S、NR 24 、CR 25 R 26 、C(O)、NR 24 C(O)、C(O)NR 24 、SO、SO 2 或共价键；其中R 24 ，R 25 和R 26 独立地为氢，烷基，环烷基，烯基，炔基，卤代烷基，芳基，氨基烷基，羟基烷基，烷氧基烷基或羧基烷基。该发明还涉及利用含有碳环和杂环取代的半卡巴松和硫代半卡巴松治疗全脑和局部缺血后的神经损伤，治疗或预防神经退行性疾病如肌萎缩侧索硬化症（ALS），治疗和预防耳神经毒性和涉及谷氨酸毒性的眼病，以及治疗、预防或改善疼痛，作为抗癫痫药，作为抗躁狂抑郁药，作为局部麻醉药，作为抗心律失常药，以及治疗或预防糖尿病性神经病变和尿失禁。

  公开号：

  US20020061886A1

文献信息

• Radical‐Transfer Hydroamination of Olefins with N‐Aminated Dihydropyridines
  作者：Chih‐Ming Chou、Joyram Guin、Christian Mück‐Lichtenfeld、Stefan Grimme、Armido Studer

  DOI：10.1002/asia.201000881

  日期：2011.5.2

  N‐phthalimidyl, benzamidyl, acetamidyl, carbamoyl, and ureayl derivatives of dihydropyridines and the application of these reagents as precursors for N‐centered radicals are presented. These aminated dihydropyridines could be used in radical‐transfer hydroamination reactions of various electron‐rich as well as nonactivated olefins in the presence of thiols as polarity‐reversal catalysts. These reactions

  N的有效合成介绍了二氢吡啶的邻苯二甲酰亚胺基，苯甲酰胺基，乙酰胺基，氨基甲酰基和脲基衍生物，以及这些试剂作为N中心自由基的前体的应用。这些胺化的二氢吡啶可在存在巯基作为极性反转催化剂的情况下，用于各种富电子以及非活化烯烃的自由基转移加氢胺化反应中。这些反应无需任何过渡金属即可进行。讨论了以N为中心的自由基的N取代基所产生的立体效应和电子效应。与大多数金属催化方法相比，自由基加氢胺化反应可提供相反的区域异构体，并具有出色的抗马尔科夫尼科夫选择性。获得加氢胺化产物，其为易于分离的受保护胺。
• Semicarbazone-based inhibitors of cathepsin K, are they prodrugs for aldehyde inhibitors?
  作者：Kim K. Adkison、David G. Barrett、David N. Deaton、Robert T. Gampe、Anne M. Hassell、Stacey T. Long、Robert B. McFadyen、Aaron B. Miller、Larry R. Miller、J. Alan Payne、Lisa M. Shewchuk、Kevin J. Wells-Knecht、Derril H. Willard、Lois L. Wright

  DOI：10.1016/j.bmcl.2005.10.108

  日期：2006.2

  Starting from potent aldehyde inhibitors with poor drug properties, derivatization to semicarbazones led to the identification of a series of semicarbazone-based cathepsin K inhibitors with greater solubility and better pharmacokinetic profiles than their parent aldehydes. Furthermore, a representative semicarbazone inhibitor attenuated bone resorption in an ex vivo rat calvarial bone resorption model. However, based on enzyme inhibition comparisons at neutral pH, semicarbazone hydrolysis rates, and 13C NMR experiments, these semicarbazones probably function as prodrugs of aldehydes.
• Feid Allah; Soliman, Pharmazie, 1980, vol. 35, # 12, p. 799 - 800
  作者：Feid Allah、Soliman

  DOI：——

  日期：——
• <i>N</i>⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor
  作者：Margot W. Beukers、Martin J. Wanner、Jacobien K. Von Frijtag Drabbe Künzel、Elisabeth C. Klaasse、Adriaan P. IJzerman、Gerrit-Jan Koomen

  DOI：10.1021/jm021074j

  日期：2003.4.1

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.
• Bougault, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1915, vol. 160, p. 625
  作者：Bougault

  DOI：——

  日期：——