N-(4-methoxyphenyl)guanidinium nitrate | 76746-74-2

• 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-(4-methoxyphenyl)guanidinium nitrate
• 英文别名: (4-methoxyphenyl)guanidinium nitrate；N-(4-methoxyphenyl)guanidine nitrate；2-(4-methoxyphenyl)guanidine;nitric acid
• CAS: 76746-74-2
• 化学式: C₈H₁₁N₃O*HNO₃
• 分子量: 228.208
• InChiKey: AQCVXPUUCPPIAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)guanidinium nitrate 在 sodium hydroxide 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4-Methoxy-phenyl)-{4-[4-(piperazine-1-sulfonyl)-phenyl]-pyrimidin-2-yl}-amine
  参考文献：
  名称：

  A novel series of potent and selective IKK2 inhibitors

  摘要：

  A novel series of ammopyrimidine IKK2 inhibitors have been developed which show excellent in vitro inhibition of this enzyme and good selectivity over the IKK1 isoform. The relative potency and selectivity of these compounds has been rationalized using QSAR and structure-based modelling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.047
• 作为产物：
  描述：

  氰胺 、 甲氧苯胺 在 硝酸 作用下， 以 乙醇 、 水 为溶剂， 以67%的产率得到N-(4-methoxyphenyl)guanidinium nitrate
  参考文献：
  名称：

  通过“切割和胶水”策略设计的7-（2-苯胺基嘧啶-4-基）-1-苯并ze庚因-2-酮是双重Aurora A / VEGF-R激酶抑制剂

  摘要：

  尽管蛋白激酶的过表达和过度活跃是导致多种人类癌症的原因，但目前被批准用作抗癌药物的蛋白激酶抑制剂仅能解决其中几种酶的问题。为了确定解决替代蛋白激酶的新化学型，将已知的PLK1 / VEGF-R2抑制剂类别的基本结构进行了正式解剖并重新组装。合成了所得的7-（2-苯胺基嘧啶丁-4-基）-1-苯并ze庚因-2-酮，并证明是Aurora A激酶和VEGF受体激酶的双重抑制剂。与Aurora A配合的新化学型的两个代表的晶体结构显示了ATP结合口袋中的配体取向，并为合理的结构修饰提供了基础。具有连接的磺酰胺取代基的同类物保留了Aurora A的抑制活性。

  DOI：

  10.3390/molecules26061611

文献信息

• Pyrazolopyridine antiherpetics: SAR of C2′ and C7 amine substituents
  作者：Brian A. Johns、Kristjan S. Gudmundsson、Elizabeth M. Turner、Scott H. Allen、Vicente A. Samano、John A. Ray、George A. Freeman、F. Leslie Boyd、Connie J. Sexton、Dean W. Selleseth、Katrina L. Creech、Kelly R. Moniri

  DOI：10.1016/j.bmc.2005.01.044

  日期：2005.4

  facile access to a diverse set of analogs from common late stage intermediates. Detailed examination of the amine substituents at the C2' position of the pyrimidine and C7 position of the core pyrazolopyridine is described. The antiviral data suggests that non-polar amines are preferred for optimal activity. Additionally, the 2' position has been shown to require an NH group to retain activity levels similar

  已鉴定出一系列新的有效的单纯疱疹病毒1复制的吡唑并[1,5-a]吡啶抑制剂。已开发了几种互补的合成方法，以使从常见的后期中间体容易获得各种类似物。描述了在嘧啶的C2'位置和核心吡唑并吡啶的C7位置上的胺取代基的详细检查。抗病毒数据表明非极性胺是最佳活性的首选。另外，已显示2'位需要一个NH基团以保持与金标准阿昔洛韦相似的活性水平。
• C–H Activation at a Bidentate Ligand Coordinated to Palladium(II) – an Electrophilic Attack Supported by an External Base
  作者：Merve Cayir、Leila Taghizadeh Ghoochany、Adam Walli、Mark Busch、Yu Sun、Franc Meyer、Stefan Bräse、Werner R. Thiel

  DOI：10.1002/ejic.201402149

  日期：2014.6

  n-4-yl)pyridines undergo C–H activation at the phenyl ring in the ortho position to the amine nitrogen atom when reacted with (PhCN)2PdCl2 and finally form N,N,C-coordinated palladium(II) complexes in high yields. Five differently substituted complexes were synthesized and characterized by spectroscopy and X-ray structure analysis. The reaction mechanism for the formation of these complexes was elucidated

  2-(2-Phenylaminopyrimidin-4-yl) 吡啶与 (PhCN)2PdCl2 反应时，在苯环胺氮原子邻位发生 C-H 活化，最终形成 N,N,C 配位钯 (II) ) 高产率的配合物。合成了五种不同取代的配合物，并通过光谱学和 X 射线结构分析对其进行了表征。通过动力学实验阐明了形成这些配合物的反应机理，从而可以计算出配合物形成的活化参数。
• Identification of 2-Anilino-9-methoxy-5,7-dihydro-6<i>H</i>-pyrimido[5,4-<i>d</i>][1]benzazepin-6-ones as Dual PLK1/VEGF-R2 Kinase Inhibitor Chemotypes by Structure-Based Lead Generation
  作者：Anne-Marie Egert-Schmidt、Jan Dreher、Ute Dunkel、Simone Kohfeld、Lutz Preu、Holger Weber、Jan E. Ehlert、Bettina Mutschler、Frank Totzke、Christoph Schächtele、Michael H. G. Kubbutat、Knut Baumann、Conrad Kunick

  DOI：10.1021/jm901388c

  日期：2010.3.25

  To develop multikinase inhibitors with dual PLK1/VEGF-R2 inhibitory activity, the d-annulated 1-benzazepin-2-one scaffold present in the paullone family of kinase inhibitors was investigated as a general structure template suitable for anchoring annulated heterocycles at the hinge region of the ATP binding site. For this purpose, the indole substructure of the paullones was replaced by other nitrogen containing heteroaromatics. The designed scaffolds were synthesized and tested on the indicated kinases. The 2-anilino-5.7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-ones were found to be VEGF-R2 inhibitors with selectivity against the insulin receptor kinase. The attachment of a methoxy group to the 9-position of the scaffold led to additional PLK1 inhibitory activity, which was explained by an alternative binding mode of the 9-methoxy derivatives. Selected members of the compound class inhibited the VEGF-R2 autophosphorylation in human umbilical vein endothelial cells, the sprouting of human umbilical vein endothelial cell speroids, and the proliferation of diverse cancer cell lines.
• 7-(2-Anilinopyrimidin-4-yl)-1-benzazepin-2-ones Designed by a “Cut and Glue” Strategy Are Dual Aurora A/VEGF-R Kinase Inhibitors
  作者：Mehmet Karatas、Apirat Chaikuad、Bianca Berger、Michael H. G. Kubbutat、Frank Totzke、Stefan Knapp、Conrad Kunick

  DOI：10.3390/molecules26061611

  日期：——

  inhibitors of Aurora A kinase and VEGF receptor kinases. Crystal structures of two representatives of the new chemotype in complex with Aurora A showed the ligand orientation in the ATP binding pocket and provided the basis for rational structural modifications. Congeners with attached sulfamide substituents retained Aurora A inhibitory activity. In vitro screening of two members of the new kinase inhibitor

  尽管蛋白激酶的过表达和过度活跃是导致多种人类癌症的原因，但目前被批准用作抗癌药物的蛋白激酶抑制剂仅能解决其中几种酶的问题。为了确定解决替代蛋白激酶的新化学型，将已知的PLK1 / VEGF-R2抑制剂类别的基本结构进行了正式解剖并重新组装。合成了所得的7-（2-苯胺基嘧啶丁-4-基）-1-苯并ze庚因-2-酮，并证明是Aurora A激酶和VEGF受体激酶的双重抑制剂。与Aurora A配合的新化学型的两个代表的晶体结构显示了ATP结合口袋中的配体取向，并为合理的结构修饰提供了基础。具有连接的磺酰胺取代基的同类物保留了Aurora A的抑制活性。
• A novel series of potent and selective IKK2 inhibitors
  作者：Alistair H. Bingham、Richard J. Davenport、Lewis Gowers、Roland L. Knight、Christopher Lowe、David A. Owen、David M. Parry、Will R. Pitt

  DOI：10.1016/j.bmcl.2003.10.047

  日期：2004.1

  A novel series of ammopyrimidine IKK2 inhibitors have been developed which show excellent in vitro inhibition of this enzyme and good selectivity over the IKK1 isoform. The relative potency and selectivity of these compounds has been rationalized using QSAR and structure-based modelling. (C) 2003 Elsevier Ltd. All rights reserved.