N-(4-羟基苯基)-N-甲基-亚硝酸酰胺 | 2976-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-羟基苯基)-N-甲基-亚硝酸酰胺
• 英文名称: N-methyl-N-nitroso-4-hydroxyaniline
• 英文别名: N-methyl-N-nitroso-4-aminophenol；N-nitroso-N-methyl-p-hydroxyaniline；4-(Methyl-nitroso-amino)-phenol；Phenol, p-(methylnitrosamino)-；N-(4-hydroxyphenyl)-N-methylnitrous amide
• CAS: 2976-94-5
• 化学式: C₇H₈N₂O₂
• 分子量: 152.153
• InChiKey: OZUFCRAEDISSPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-羟基苯基)-N-甲基-亚硝酸酰胺 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 25.0~40.0 ℃ 、324.05 kPa 条件下， 反应 16.25h， 生成 1-[N-methyl-N-(4-hydroxyphenyl)amino]pyrrole
  参考文献：
  名称：

  Synthesis and antibacterial activity of 1-(arylamino)-1H-pyrroles and 4-(1H-pyrrol-1-ylimino)-2,5-cyclohexadienes

  摘要：

  The syntheses of 1-(arylamino)-1H-pyrroles and 4-(1H-pyrrol-1-ylimino)-2-5-cyclohexadienes are described. Several of these compounds express in vitro antibacterial activity or can be metabolized to show in vitro antibacterial activity, and a few examples have shown efficacy against tuberculosis in mice. One compound, N,N'-(2,5-cyclohexadiene-1,4-diylidene)bis-1H-pyrrol-1-amine, is completely effective at 6.25 mg/kg against Mycobacterium tuberculosis H37Rv.

  DOI：

  10.1021/jm00143a011
• 作为产物：
  描述：

  对甲氨基酚 在 溶剂黄146 、 sodium nitrite 作用下， 反应 1.0h， 以76%的产率得到N-(4-羟基苯基)-N-甲基-亚硝酸酰胺
  参考文献：
  名称：

  PeptidylN-亚硝基苯胺：一类新型半胱氨酸蛋白酶灭活剂†,‡

  摘要：

  一系列肽基 N-亚硝基苯胺被设计、合成并评估为半胱氨酸蛋白酶木瓜蛋白酶和丝氨酸蛋白酶糜蛋白酶的灭活剂。这些新化合物以时间和浓度依赖性方式对半胱氨酸蛋白酶木瓜蛋白酶表现出不同的抑制活性，二级速率常数 (kinact/KI) 范围从 0.604 M-1 s-1 (1) 到 2 个数量级。 100.36 M-1 s-1 (7)。没有观察到丝氨酸蛋白酶糜蛋白酶失活。木瓜蛋白酶中 S-NO 键的形成得到了光谱研究和化学分析的几条证据的支持。在 3.2-9.2 的 pH 范围内进行化合物 1 灭活木瓜蛋白酶的 pH 曲线研究，以提供对灭活过程机制的更多了解。

  DOI：

  10.1021/ja974187e

文献信息

• A hypoxia-activated NO donor for the treatment of myocardial hypoxia injury
  作者：Wen Zhou、Wanxiang Yang、Keyu Fan、Wuyang Hua、Shaohua Gou

  DOI：10.1039/d2sc00048b

  日期：——

  A novel HAP-type NO donor was found to release NO under hypoxia locally. It dilates blood vessels in smooth muscle cells and attenuates myocardial hypoxia injury in cardiomyocytes.

  发现一种新型的HAP型NO供体，可以在缺氧状态下局部释放NO。它可以扩张平滑肌细胞中的血管，并减轻心肌细胞中的心肌缺氧损伤。
• Photoinduced NO-release from polymer dots doped with an Ir(<scp>iii</scp>) complex and <i>N</i>-methyl-<i>N</i>-nitroso-4-aminophenol
  作者：Daisuke Saitoh、Ayumi Suzuki、Naoya Ieda、Zuoyue Liu、Yasuko Osakada、Mamoru Fujitsuka、Mitsuyasu Kawaguchi、Hidehiko Nakagawa

  DOI：10.1039/d3ob00047h

  日期：——

  New NO-generating nanoparticles employing an intermolecular photoredox reaction successfully released NO upon blue light irradiation in vitro.

  采用分子间光氧化反应的新型 NO 生成纳米粒子在体外蓝光照射下成功释放 NO。
• Photocontrollable Peroxynitrite Generator Based on <i>N</i>-Methyl-<i>N</i>-nitrosoaminophenol for Cellular Application
  作者：Naoya Ieda、Hidehiko Nakagawa、Tao Peng、Dan Yang、Takayoshi Suzuki、Naoki Miyata

  DOI：10.1021/ja206744z

  日期：2012.2.8

  We designed and synthesized a photocontrollable peroxynitrite (ONOO-) generator, P-NAP, which has N-methyl-N-nitrosoaminophenol structure with four methyl groups photodecomposition product with ONOO- and to lower the introduced onto the benzene ring to block reaction of the semiquinoneimine's redox potential. The semiquinoneimine intermediate generated by photoinduced release of nitric oxide (NO) reduces dissolved molecular oxygen to generate superoxide radical anion (O-2(center dot-)), which reacts with NO to afford ONOO- under diffusion control (k = 6.7 X 10(9) M-1 s(-1)). NO release from P-NAP under UV-A (330-380 nm) irradiation was confirmed by ESR spin trapping. Tyrosine nitration, characteristic of ONOO-, was demonstrated by HPLC analysis of a photoirradiated aqueous solution of P-NAP and N-acetyl-L-tyrosine ethyl ester. ONOO- formation was confirmed with a ONOO--specific fluorogenic probe, HKGreen-3, and compared with that from 3-(4-morpholinyl)sydnonimine hydrochloride (SIN-1), which is the most widely used ONOO- generator at present. The photoreaction of P-NAP was influenced by superoxide dismutase, indicating that generation of O-2(center dot-) occurs before ONOO- formation. The quantum yield for formation of duroquinone, the main P-NAP photodecomposition product, was measured as 0.86 +/- 0.07 at 334 nm with a potassium ferrioxalate actinometer. Generation of ONOO- from P-NAP in HCT-116 cells upon photoirradiation was successfully imaged with HKGreen-3A. This is the first example of a photocontrollable ONOO- donor applicable to cultured cells.
• 259. New methods in stereochemistry. Part III. Some new optically active reagents for ketones and aldehydes
  作者：Alfred S. Galloway、John Read

  DOI：10.1039/jr9360001222

  日期：——
• The Reduction of p-Hydroxyformanilide by Lithium Aluminum Hydride to N-Methyl-p-aminophenol
  作者：Jacob Ehrlich

  DOI：10.1021/ja01186a506

  日期：1948.6