phenyl N'-cyano-N-(2-methoxyphenyl)carbamimidate | 700804-74-6

• 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: phenyl N'-cyano-N-(2-methoxyphenyl)carbamimidate
• 英文别名: (Z)-1-cyano-3-(2-methoxyphenyl)-2-phenylisourea；phenyl N-cyano-N'-(2-methoxyphenyl)carbamimidate
• CAS: 700804-74-6
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: USTFUYCZIUTHML-UHFFFAOYSA-N

物化性质

• 沸点：
  408.9±47.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl N'-cyano-N-(2-methoxyphenyl)carbamimidate 、 1-(1-金刚烷)甲胺盐酸盐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以86%的产率得到1-(adamantan-1-ylmethyl)-2-cyano-3-(2-methoxyphenyl)guanidine
  参考文献：
  名称：

  Discovery and pharmacological evaluation of a novel series of adamantyl cyanoguanidines as P2X7 receptor antagonists

  摘要：

  Here we report adamantyl cyanoguanidine compounds based on hybrids of the adamantyl amide scaffold reported by AstraZeneca and cyanoguanidine scaffold reported by Abbott Laboratories. Compound 27 displayed five-fold greater inhibitory potency than the lead compound 2 in both pore-formation and interleukin-1 beta release assays, while 35-treated mice displayed an antidepressant phenotype in behavioral studies. This SAR study provides a proof of concept for hybrid compounds, which will help in the further development of P2X(7)R antagonists. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.060
• 作为产物：
  描述：

  邻甲氧基苯胺 、 N-氰基羰亚胺二苯基酯 以 乙腈 为溶剂， 反应 16.0h， 以78%的产率得到phenyl N'-cyano-N-(2-methoxyphenyl)carbamimidate
  参考文献：
  名称：

  Discovery and pharmacological evaluation of a novel series of adamantyl cyanoguanidines as P2X7 receptor antagonists

  摘要：

  Here we report adamantyl cyanoguanidine compounds based on hybrids of the adamantyl amide scaffold reported by AstraZeneca and cyanoguanidine scaffold reported by Abbott Laboratories. Compound 27 displayed five-fold greater inhibitory potency than the lead compound 2 in both pore-formation and interleukin-1 beta release assays, while 35-treated mice displayed an antidepressant phenotype in behavioral studies. This SAR study provides a proof of concept for hybrid compounds, which will help in the further development of P2X(7)R antagonists. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.060

文献信息

• Diaminotriazoles useful as inhibitors of protein kinases
  申请人：——

  公开号：US20040214817A1

  公开（公告）日：2004-10-28

  The present invention relates to inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及蛋白激酶抑制剂。本发明还提供了包含本发明化合物的制药组合物以及使用该组合物治疗各种疾病的方法。
• Piperazines as P2X7 antagonists
  申请人：Betschmann Patrick

  公开号：US20080076924A1

  公开（公告）日：2008-03-27

  Novel compounds of Formula (I) or pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, enantiomers thereof or prodrugs thereof of Formula (I) wherein the substituents are as defined herein, which are useful as therapeutic agents.

  化合物I式的新型化合物或其药学上可接受的盐、代谢物、异构体、对映体或前药，其中取代基如本文所定义，这些化合物可用作治疗剂。
• DIAMINOTRIAZOLES USEFUL AS INHIBITORS OF PROTEIN KINASES
  申请人：Pierce C. Albert

  公开号：US20080014189A1

  公开（公告）日：2008-01-17

  The present invention relates to inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及蛋白激酶抑制剂。该发明还提供了包含本发明化合物的药物组合物以及使用该组合物治疗各种疾病的方法。
• [EN] DIAMINOTRIAZOLES USEFUL AS INHIBITORS OF PROTEIN KINASES<br/>[FR] DIAMINOTRIAZOLES CONVENANT COMME INHIBITEURS DE PROTEINE KINASES
  申请人：VERTEX PHARMA

  公开号：WO2004046120A3

  公开（公告）日：2004-08-12
• Design, Synthesis, and Evaluation of a Novel Dual Fms-Like Tyrosine Kinase 3/Stem Cell Factor Receptor (FLT3/c-KIT) Inhibitor for the Treatment of Acute Myelogenous Leukemia
  作者：Robert J. Davies、Albert C. Pierce、Cornelia Forster、Ron Grey、Jinwang Xu、Michael Arnost、Deborah Choquette、Vincent Galullo、Shi-Kai Tian、Greg Henkel、Guanjing Chen、David K. Heidary、Joanne Ma、Cameron Stuver-Moody、Mark Namchuk

  DOI：10.1021/jm200712h

  日期：2011.10.27

  A high-throughput screen of our compound archive revealed a novel class of dual FMS-like tyrosine kinase 3 (FLT3)/c-KIT inhibitors. With the help of molecular modeling, this class was rapidly optimized for both potency against FLT3 and FLT3/c-KIT and excellent potency in cell-based assays, leading to dose-dependent cell death in acute myelogenous leukemia (AML) patient blast samples. Ultimately, the AML patient blast data defined the preferred target profile as we designed and evaluated a set of FLT3 selective and FLT3/c-KIT dual molecules. Further optimization for pharmacokinetic properties resulted in the selection of the dual FLT3/c-KIT inhibitor, N-3-(4-(trans-4-morpholinocyclohexyl)phenyl)-1-(pyridin-2-yl)-1H-1,2,4-triazole-3,5-diamine, VX-322 (compound 37), to move forward to preclinical evaluation.