n,n'-Bis-cbz-n''-(2-hydroxyethyl)guanidine | 476667-20-6

• 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: n,n'-Bis-cbz-n''-(2-hydroxyethyl)guanidine
• 英文别名: benzyl N-[N'-(2-hydroxyethyl)-N-phenylmethoxycarbonylcarbamimidoyl]carbamate
• CAS: 476667-20-6
• 化学式: C₁₉H₂₁N₃O₅
• 分子量: 371.393
• InChiKey: UCZGDGVIEVFOAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  n,n'-Bis-cbz-n''-(2-hydroxyethyl)guanidine 在 盐酸 、 Ph₂PC₆H₄-polymer 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 2-[9-[2-[bis(phenylmethoxycarbonylamino)methylideneamino]ethoxy]-2-oxo-10H-pyrimido[5,4-b][1,4]benzoxazin-3-yl]acetic acid
  参考文献：
  名称：

  Synthesis of Amino- and Guanidino-G-Clamp PNA Monomers

  摘要：

  [GRAPHICS]Syntheses of the protected amino- and guanidino-G-clamp PNA monomers, 9a and 9b, respectively, have been accomplished in eight steps from 5-bromouracil. Enhanced stacking interactions and additional hydrogen bonds with guanine should increase the affinity of PNAs incorporating these cytosine analogues for their complementary strands.

  DOI：

  10.1021/ol026815p
• 作为产物：
  描述：

  C.I.酸性橙108 、 1,3-二(苄氧羰基)-2-甲基异硫脲 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以36%的产率得到n,n'-Bis-cbz-n''-(2-hydroxyethyl)guanidine
  参考文献：
  名称：

  Synthesis of Amino- and Guanidino-G-Clamp PNA Monomers

  摘要：

  [GRAPHICS]Syntheses of the protected amino- and guanidino-G-clamp PNA monomers, 9a and 9b, respectively, have been accomplished in eight steps from 5-bromouracil. Enhanced stacking interactions and additional hydrogen bonds with guanine should increase the affinity of PNAs incorporating these cytosine analogues for their complementary strands.

  DOI：

  10.1021/ol026815p

文献信息

• [EN] PYRIMIDINES AND VARIANTS THEREOF, AND USES THEREFOR<br/>[FR] PYRIMIDINES ET VARIANTES DE CELLES-CI, ET LEURS UTILISATIONS
  申请人：AFFERENT PHARMACEUTICALS INC

  公开号：WO2017160569A1

  公开（公告）日：2017-09-21

  The present disclosure provides pyrimidine compounds and uses thereof, for example, for the treatment of diseases associated with P2X purinergic receptors. In certain aspects, the present disclosure provides P2X3 and/or P2X2/3 antagonists which are useful, for example, for the treatment of visceral organ, cardiovascular and pain-related diseases, conditions and disorders.

  本公开提供嘧啶化合物及其用途，例如用于治疗与P2X嘌呤受体相关的疾病。在某些方面，本公开提供P2X3和/或P2X2/3拮抗剂，这些拮抗剂可用于治疗内脏器官、心血管和与疼痛相关的疾病、症状和障碍。
• Identification and SAR of novel diaminopyrimidines. Part 2: The discovery of RO-51, a potent and selective, dual P2X3/P2X2/3 antagonist for the treatment of pain
  作者：Alam Jahangir、Muzaffar Alam、David S. Carter、Michael P. Dillon、Daisy Joe Du Bois、Anthony P.D.W. Ford、Joel R. Gever、Clara Lin、Paul J. Wagner、Yansheng Zhai、Jeff Zira

  DOI：10.1016/j.bmcl.2009.01.097

  日期：2009.3

  The purinoceptor subtypes P2X(3) and P2X(2/3) have been shown to play a pivotal role in models of various pain conditions. Identification of a potent and selective dual P2X(3)/P2X(2/3) diaminopyrimidine antagonist RO-4 prompted subsequent optimization of the template. This paper describes the SAR and optimization of the diaminopyrimidine ring and particularly the substitution of the 2-amino group. The discovery of the highly potent and drug-like dual P2X(3)/P2X(2/3) antagonist RO-51 is presented. (C) 2009 Elsevier Ltd. All rights reserved.
• Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2
  作者：James F. Blake、John J. Gaudino、Jason De Meese、Peter Mohr、Mark Chicarelli、Hongqi Tian、Rustam Garrey、Allen Thomas、Christopher S. Siedem、Michael B. Welch、Gabrielle Kolakowski、Robert Kaus、Michael Burkard、Matthew Martinson、Huifen Chen、Brian Dean、Danette A. Dudley、Stephen E. Gould、Patricia Pacheco、Sheerin Shahidi-Latham、Weiru Wang、Kristina West、Jianping Yin、John Moffat、Jacob B. Schwarz

  DOI：10.1016/j.bmcl.2014.04.068

  日期：2014.6

  The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Amino- and Guanidino-G-Clamp PNA Monomers
  作者：Cristina Ausín、José-Antonio Ortega、Jordi Robles、Anna Grandas、Enrique Pedroso

  DOI：10.1021/ol026815p

  日期：2002.11.1

  [GRAPHICS]Syntheses of the protected amino- and guanidino-G-clamp PNA monomers, 9a and 9b, respectively, have been accomplished in eight steps from 5-bromouracil. Enhanced stacking interactions and additional hydrogen bonds with guanine should increase the affinity of PNAs incorporating these cytosine analogues for their complementary strands.