3-cyano-1-ethyl-2-phenylisourea | 20494-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-cyano-1-ethyl-2-phenylisourea
• 英文别名: N-Ethyl-O-phenyl-N'-cyan-isoharnstoff；1-cyano-3-ethyl-2-phenylisourea；Phenyl N-cyano-N'-ethylcarbamimidate
• CAS: 20494-36-4
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: SBNYPMOAKGZBJH-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  275.8±23.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyano-1-ethyl-2-phenylisourea 、 5-(4-咪唑)戊胺 以 乙腈 为溶剂， 反应 0.05h， 以83%的产率得到2-cyano-1-ethyl-3-[5-(1H-imidazol-4-yl)pentyl]guanidine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Cyanoguanidine-Type and Structurally Related Histamine H₄ Receptor Agonists

  摘要：

  Recently, we identified high-affinity human histamine H-3 (hH(3)R) and H-4 receptor (hH(4)R) ligands among a series of N-G-acylated imidazolylpropylguanidines, which were originally designed as histamine H-2 receptor (H2R) agonists. Aiming at selectivity for hH(4)R, the acylguanidine group was replaced with related moieties. Within a series of cyanoguanidines, 2-cyano-1-[4-(1H-imidazol-4-yl)butyl]-3-[(2-phenylthio)ethyl]guanidine (UR-PI376, 67) was identified as the most potent hH(4)R agonist (pEC(50) = 7.47, alpha = 0.93) showing negligible hH(1)R and hH(2)R activities and significant selectivity over the hH(3)R (pK(B) = 6.00, alpha = -0.28), as determined in steady-state GTPase assays using. membrane preparations of hH(x)R-expressing Sf9 cells. In contrast to previously described selective H4R agonists, this compound and other 3-substituted derivatives are devoid of agonistic activity at the other HR subtypes. Modeling of the binding mode of 67 suggests that the cyanoguanidine moiety forms charge-assisted hydrogen bonds not only with the conserved Asp-94 but also with the hH(4)R-specific Arg-341 residue. 2-Carbamoyl-1-[2-(1H-imidazol-4-yl)ethyl]-3-(3-phenylpropyl)guanidine (UR-PI97, 88) was unexpectedly identified as a highly potent and selective hH(3)R inverse agonist (pK(B) = 8.42, > 300-fold selectivity over the other HR subtypes).

  DOI：

  10.1021/jm900526h
• 作为产物：
  描述：

  N-氰基羰亚胺二苯基酯 、 乙胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 3-cyano-1-ethyl-2-phenylisourea
  参考文献：
  名称：

  [EN] THIOPHENE DERIVATIVES FOR THE TREATMENT OF DISORDERS CAUSED BY IGE
  [FR] DÉRIVÉS DE THIOPHÈNE POUR LE TRAITEMENT DE TROUBLES PROVOQUÉS PAR IGE

  摘要：

  提供了公式（I）的噻吩衍生物及其药用可接受的盐。这些化合物对于治疗或预防由IgE引起的疾病具有用途，如过敏、1型超敏反应或家族性鼻窦炎。

  公开号：

  WO2019243550A1

文献信息

• Cycloalkyl inhibitors of potassium channel function
  申请人：——

  公开号：US20040072880A1

  公开（公告）日：2004-04-15

  Novel cycloalkyl compounds useful as inhibitors of potassium channel function (especially inhibitors of the K v 1 subfamily of voltage gated K + channels, especially inhibitors K v 1.5 which has been linked to the ultra-rapidly activating delayed rectifier K + current I Kur ), methods of using such compounds in the prevention and treatment of arrhythmia and I Kur -associated conditions, and pharmaceutical compositions containing such compounds.

  新型环烷基化合物可用作钾通道功能抑制剂（特别是Kv1亚家族电压门控K+通道的抑制剂，特别是抑制与超快速激活延迟整流K+电流IKur相关的Kv1.5），使用这些化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有这些化合物的制药组合物。
• CYCLOALKYL INHIBITORS OF POTASSIUM CHANNEL FUNCTION
  申请人：Lloyd John

  公开号：US20070142333A1

  公开（公告）日：2007-06-21

  Novel cycloalkyl compounds useful as inhibitors of potassium channel function (especially inhibitors of the K v 1 subfamily of voltage gated K + channels, especially inhibitors K v 1.5 which has been linked to the ultra-rapidly activating delayed rectifier K + current I Kur ), methods of using such compounds in the prevention and treatment of arrhythmia and I Kur -associated conditions, and pharmaceutical compositions containing such compounds.

  新型环烷基化合物可作为钾通道功能抑制剂使用（特别是钾离子电压门控K+通道的Kv1亚家族的抑制剂，特别是与超快速激活延迟整流K+电流IKur相关的Kv1.5抑制剂），使用这种化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有这种化合物的药物组合物。
• Martin,D. et al., Chemische Berichte, 1968, vol. 101, # 9, p. 3185 - 3200
  作者：Martin,D. et al.

  DOI：——

  日期：——
• THIOPHENE DERIVATIVES FOR THE TREATMENT OF DISORDERS CAUSED BY IGE
  申请人：UCB Biopharma SRL

  公开号：EP3810606A1

  公开（公告）日：2021-04-28
• Novel Substituted 4-Phenyl-4[H-Imidazol-2-YL]-Piperidine Derivatived And Their Use As Selective Non-Peptide Delta Opioid Agonists
  申请人：Janssens Eduard Frans

  公开号：US20080096925A1

  公开（公告）日：2008-04-24

  The present invention relates to novel 4-phenyl-4-[ 1 H-imidazol-2-yl]-piperidine derivatives according to Formula (I) the pharmaceutically acceptable acid or base addition salts thereof, the stereochemically isomeric forms thereof, the tautomeric forms thereof and the N-oxide forms thereof. In particular are claimed compounds according to Formula (I) in which A=B is C═O or SO 2 , X is a covalent bond, R 1 is alkyloxy, alkyloxyalkyl, Ar or NR 9 R 10 , wherein R 9 and R 10 each independently are hydrogen or Ar; or A=B and R 1 together form a benzoxazolyl radical; p is zero, R 3 is benzyl optionally substituted with hydroxy, alkyl or alkyloxycarbonyl and R 4 and R 5 each are hydrogen. The invention also relates to processes for the preparation of the compounds according to the invention and their use in medicine, in particular as selective non-peptide δ-opioid agonists for use in the treatment of various pain conditions.