4-Nitro-benzylcyanamid | 98555-07-8

• 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: 4-Nitro-benzylcyanamid
• 英文别名: (4-Nitrophenyl)methylcyanamide
• CAS: 98555-07-8
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: ZJFYGGYPVFSEFU-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  343.5±44.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 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：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Nitro-benzylcyanamid 在 羟胺 作用下， 以 甲醇 为溶剂， 生成 N-(4-nitro)benzyl-N'-hydroxyguanidine
  参考文献：
  名称：

  Electrochemical and peroxidase oxidation study of N′-Hydroxyguanidine derivatives as NO donors

  摘要：

  The electrochemical properties of a series of N-substituted-N-hydroxyguanidines were studied. Two oxidation potentials of each compound were obtained by cyclic voltammetry. The E-ox1 values were from 0.51 to 0.62V, while the E-ox2 Values were from 1.14 to 1.81V in acetonitrile solution. Next, their enzymatic controlled NO release abilities were evaluated. All N'-hydroxyguanidines exhibited efficient NO release abilities under the oxidation by horseradish peroxidase in the presence Of H2O2. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00185-3
• 作为产物：
  描述：

  在 水 作用下， 生成 4-Nitro-benzylcyanamid
  参考文献：
  名称：

  N-Nitrosated N-hydroxyguanidines are nitric oxide-releasing diazeniumdiolates

  摘要：

  N-Hydroxyguanidines 可被亚硝基转化为具有晶体学确认结构 H2N+C[NHR][N(O)NO]- 的齐聚二氮杂环戊酸酯，其在生理 pH 值下的水解解离可产生 NO 和 N2O；这些结果似乎解释了将 NG-羟基-L-精氨酸（哺乳动物 NO 生物合成过程中的代谢中间产物）暴露于有氧 NO 时产生的 "潜在细胞间一氧化氮载体 "的形成原因。

  DOI：

  10.1039/a801543k

文献信息

• Copper-Catalyzed Domino Three-Component Approach for the Assembly of 2-Aminated Benzimidazoles and Quinazolines
  作者：Lam Quang Tran、Jihui Li、Luc Neuville

  DOI：10.1021/acs.joc.5b00614

  日期：2015.6.19

  A copper-promoted three-component synthesis of 2-aminobenzimidazoles (1) or of 2-aminoquinazolines (2) involving cyanamides, arylboronic acids, and amines has been developed. The operationally simple oxidative process, performed in the presence of K2CO3, a catalytic amount of CuCl2·2H2O, 2,2′-bipyridine, and an O2 atmosphere (1 atm), allows the rapid assembly of either benzimidazoles or quinazolines

  已经开发了一种铜促进的三组分合成2-氨基苯并咪唑（1）或2-氨基喹唑啉（2）的方法，该方法涉及氰胺，芳基硼酸和胺。在K 2 CO 3，催化量的CuCl 2 ·2H 2 O，2,2'-联吡啶和O 2气氛（1个大气压）的存在下进行的操作简单的氧化过程可以使任何一种的快速组装分别从芳基或苄基取代的氰胺开始的苯并咪唑或喹唑啉。在这个过程中，铜促进了三个键，两个C–N键以及一个由CH–H功能化事件产生的额外键的形成。
• Novel substrates for nitric oxide synthases
  作者：Ming Xian、Noriko Fujiwara、Zhong Wen、Tingwei Cai、Satoshi Kazuma、Adam J Janczuk、Xiaoping Tang、Vladislav V Telyatnikov、Yingxin Zhang、Xinchao Chen、Yasuhide Miyamoto、Naoyuki Taniguchi、Peng George Wang

  DOI：10.1016/s0968-0896(02)00155-4

  日期：2002.9

  Enzymatic generation of nitric oxide (NO) by nitric oxide synthase (NOS) consists of two oxidation steps. The first step converts L-arginine to N-G-hydroxy-L-arginine (NOHA), a key intermediate, and the second step converts NOHA to NO and L-citrulline. To fully probe the substrate specificity of the second enzymatic step, an extensive structural screening was carried out using a series of N-alkyl (and N-aryl) substituted-N'-hydrosyguanidines (1-14). Among the eleven N-alkyl-N'-hydroxyguanidines evaluated, N-n-propyl (2). N-iso-propyl (3). N-n-butyl (4). N-s-butyl (5). N-iso-butyl (6), N-pentyl (8) and N-iso-pentyl (9) derivatives were efficiently oxidized by the three isoenzymes of NOS (nNOS, iNOS and eNOS) to generate NO. N-Butyl-N'-hydroxyguanidine (4) was the best substrate for iNOS (K-m = 33 muM) and N-iso-propyl-N'-hydroxyguanidine (3) was the best substrate for nNOS (K-m = 56 muM). When the alkyl substituents were too small (such as ethyl 1) or too large (such as hexyl 10 and cyclohexyl 11) the activity decreased significantly. This suggests that the van der Waals interaction between the alkyl group and the hydrophobic cavity in the NOS active site contributes significantly to the relative reactivity of compounds 3-11. Moreover, five N-aryl-N'-hydroxyguanidines were found to be good substrates for iNOS. but not substrates for eNOS and nNOS. N-phenyl-N'-hydroxy- guanidine was the best substrate among them (K-m = 243 muM). This work demonstrates that N-alkyl substituted hydroxyguanidine compounds are novel NOS substrates which 'short-circuit' the first oxidation step of NOS, and N-aryl substituted hydroxyguanidine compounds are isoform selective NOS substrate. (C) 2002 Published by Elsevier Science Ltd.