2-cyano-2-isonitroso-N-morpholylacetamide | 76104-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-cyano-2-isonitroso-N-morpholylacetamide
• 英文别名: N-hydroxy-2-morpholino-2-oxoacetimidoyl cyanide；2-isonitroso-2-cyano-N-morpholylacetamide；2-oximino-2-cyano-N-morpholylacetamide；N-morpholyl-2-cyano-2-oximinoacetamide；2-hydroxyimino-3-morpholin-4-yl-3-oxopropanenitrile
• CAS: 76104-20-6
• 化学式: C₇H₉N₃O₃
• 分子量: 183.167
• InChiKey: FHGCOOQCCSYHCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.92
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-cyano-2-isonitroso-N-morpholylacetamide 在 potassium carbonate 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 Pt(2-oximino-2-cyano-N-morpholylacetamide)₂
  参考文献：
  名称：

  短波红外发光铂纳米线：溶液和固态发射的机理研究

  摘要：

  已获得并表征了几种含有两个氰基肟阴离子的“PtL2”复合物 - 2-肟基-2-氰基-N-哌啶乙酰胺（PiPCO-）和2-肟基-2-氰基-N-吗啉基乙酰胺（MCO-）无论是在溶液中还是在固态中。配合物以两种不同的多晶型存在：单体黄色配合物和深绿色[PtL2]n 1D 聚合物，而对于MCO-阴离子，还分离出含有二聚[Pt(MCO)2xDMSO]2 配合物的红色溶剂。研究了多晶型物的相互转化。单体 PtL2 单元借助 Pt---Pt 亲金属相互作用排列成各向异性扩展固体 [PtL2]n 聚合物。测定了单体 PtL2 (L= PiP-CO-, MCO-) 和红色二聚体 [Pt(MCO)2xDMSO]2 配合物的晶体结构，并揭示了氰肟阴离子的顺式排列。发现“头尾”红色二聚体中的 Pt-Pt 距离为 3.133 Å。使用 EXAFS 方法阐明了聚合 [Pt(PiPCO)2]n 化合物的结构，并证明了具有约

  DOI：

  10.1039/c7dt02317k
• 作为产物：
  描述：

  N-氰乙酰基吗啡啉 在 亚硝酸甲酯 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 2-cyano-2-isonitroso-N-morpholylacetamide
  参考文献：
  名称：

  氰基乙酰胺基肟碳酸盐：一种有效的，简单的替代方法，可将Fmoc引入而使二肽的形成最少

  摘要：

  如今，大多数肽由于其完全正交的特性，温和的临时基团去除和树脂裂解步骤而通过使用Fmoc / t Bu保护策略化学合成。但是，它被引入到N中-未保护的氨基酸不能免除合成上的不便，例如二肽的形成。最近，在用于Fmoc引入的试剂库中引入了新型的肟肟碳酸盐，其副产物的百分含量几乎可以忽略不计。在此，提出了该家族的Fmoc-碳酸酯的强制形式，其包含稳定和高酸性的基于氰基乙酰胺的肟作为离去基团。从简单易得的起始原料仅需两个步骤即可负担得起的此类反应物种，显示出以高产率获得相应的Fmoc保护的残基的异常能力，而有害副产物（主要是Fmoc-二肽）的影响最小。

  DOI：

  10.1016/j.tet.2012.02.020

文献信息

• Synthesis, Characterization and Anti-proliferation Activities of Novel Cyano Oximino Sulfonate Esters
  作者：Ayman El-Faham、Yasser Abbas Elnakdy、Sarah Abdou Mohamed El Gazzar、Mohamed Mokbel Abd El-Rahman、Sherine Nabil Khattab

  DOI：10.1248/cpb.c13-01005

  日期：——

  A series of novel cyano oximino sulfonate derivatives were prepared from the reaction of arylsulfonyl chloride with different cyanoacetamide-based oximes ranging from the simplest unsubstituted amide to analogues containing N-ethyl (mimicking the Oxyma template), N-piperidinyl and N-morpholinyl chains. In addition, the cyano oximes, N-hydroxybenzimidoyl cyanide and N-hydroxypicolinimidoyl cyanide were also used in the synthesis of the novel cyano oximino sulfonate derivatives. The structures of the prepared compounds were confirmed by 1H-NMR, 13C-NMR, and elemental analysis. The preliminary bioassays showed that some of the title compounds, such as 2-oxo-2-(piperidin-1-yl)-N-(tosyloxy)acetimidoyl cyanide (TsPipOx), N-(tosyloxy)benzimidoyl cyanide (TsPhOX), N-(naphthalen-2-ylsulfonyloxy)-2-oxo-2-(piperidin-1-yl)acetimidoyl cyanide (NpsPipOx), 2-amino-N-(naphthalen-2-ylsulfonyloxy)-2-oxoacetimidoyl cyanide (NpsAmOx), N-(naphthalen-2-ylsulfonyloxy)benzimidoyl cyanide (NpsPhCN), and N-(naphthalen-2-ylsulfonyloxy)picolinimidoyl cyanide (NpsPyCN), showed anti-proliferation effect on the mouse fibroblast L929. The calculated IC50-values were ranging between 36.5 µg/mL and 0.235 mg/mL. However the anti-proliferation effects seem to be cytostatic rather than cytotoxic. The compounds only minimize the growth activity without completely killing the cells.

  通过芳基磺酰氯与不同的氰基乙酰胺基肟的反应制备了一系列新型氰基肟基磺酸盐衍生物，范围从最简单的未取代酰胺到含有 N-乙基（模仿 Oxyma 模板）、N-哌啶基和 N-吗啉基链的类似物。此外，氰基肟、N-羟基苯甲亚胺基氰化物和N-羟基吡啶亚胺基氰化物也被用于合成新型氰基肟基磺酸盐衍生物。所制备的化合物的结构通过1H-NMR、13C-NMR和元素分析进行​​了确认。初步生物测定表明，一些标题化合物，如 2-oxo-2-(piperidin-1-yl)-N-(tosyloxy)acetimidoyl colonide (TsPipOx)、N-(tosyloxy)benzimidoyl colonide (TsPhOX)、N -(萘-2-基磺酰氧基)-2-氧代-2-(哌啶-1-基)乙酰亚氨基氰化物(NpsPipOx)、2-氨基-N-(萘-2-基磺酰氧基)-2-氧代乙酰亚氨基氰化物(NpsAmOx)、 N-(萘-2-基磺酰氧基)苯并亚胺酰氰化物 (NpsPhCN) 和 N-(萘-2-基磺酰氧基)吡啶亚胺酰氰化物 (NpsPyCN) 对小鼠成纤维细胞 L929 显示出抗增殖作用。计算出的 IC50 值范围在 36.5μg/mL 至 0.235mg/mL 之间。然而，抗增殖作用似乎是细胞抑制作用而不是细胞毒性作用。这些化合物只会最大限度地减少生长活性，而不会完全杀死细胞。
• Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates
  作者：Courtney N. Riddles、Mark Whited、Shalaka R. Lotlikar、Korey Still、Marianna Patrauchan、Svitlana Silchenko、Nikolay Gerasimchuk

  DOI：10.1016/j.ica.2013.12.006

  日期：2014.3

  High-yield syntheses of N-piperidine-cyanacetamide (1), N-morpholyl-cyanacetamide (4) and their oxime derivatives N-piperidine-2-cyano-2-oximino-acetamide (HPiPCO, 2) and N-morpholyc-2-cyano-2-oximino-acetamide (HMCO, 5) were developed using two-step preparations. At first, the reactions of neat cyanoacetic acid esters and the respective cyclic secondary amines such as piperideine and morpholine afforded

  N-哌啶-氰乙酰胺（1），N-吗啉基-氰乙酰胺（4）及其肟衍生物N-哌啶-2-氰基-2-肟基乙酰胺（HPiPCO，2）和N-吗啉-2的高产率合成-氰基-2-肟基乙酰胺（HMCO，5）使用两步制备方法开发。首先，纯净的氰基乙酸酯与相应的环状仲胺（例如哌啶和吗啉）进行反应，得到纯的氰基乙酰胺，然后在室温下使用气态CH3ONO进行亚硝化反应，将其转化为氰基肟。通过IR，1H，13C和UV-可见光谱对合成的化合物进行了研究。确定了两个起始取代的氰基乙酰胺和两个目标氰基肟的晶体结构。高产AgL组成的银（I）配合物（L = PiPCO，3； MCO，6）。两种金属络合物在100oC以上的温度下均具有热稳定性，并且对高强度可见光具有显着的稳定性。使用扩散反射光谱法检查了干燥的AgL化合物对短波长紫外线辐射（一种常用的杀菌光）的稳定性。两种络合物均在约3小时内显示出缓慢的光还原，可观察到由于金属银细颗粒（
• Non-Antibiotic Antimony-Based Antimicrobials
  作者：Nikolay Gerasimchuk、Kevin Pinks、Tarosha Salpadoru、Kaitlyn Cotton、Olga Michka、Marianna A. Patrauchan、Karen L. Wozniak

  DOI：10.3390/molecules27217171

  日期：——

  A series of the eight novel organoantimony(V) cyanoximates of Sb(C6H5)4L composition was synthesized using the high-yield heterogeneous metathesis reaction between solid AgL (or TlL) and Sb(C6H5)4Br in CH3CN at room temperature. Cyanoximes L were specially selected from a large group of 48 known compounds of this subclass of oximes on the basis of their water solubility and history of prior biological activity. The synthesized compounds are well soluble in organic solvents and were studied using a variety of conventional spectroscopic and physical methods. The crystal structures of all reported organometallic compounds were determined and revealed the formation of the distorted trigonal bipyramidal environment of the Sb atom and monodentate axial binding of acido-ligands via the O atom of the oxime group. The compounds are thermally stable in the solid state and in solution molecular compounds. For the first time, this specially designed series of organoantimony(V) compounds is investigated as potential non-antibiotic antimicrobial agents against three bacterial and two fungal human pathogens known for their increasing antimicrobial resistance. Bacterial pathogens included Gram-negative Escherichia coli and Pseudomonas aeruginosa, and Gram-positive Staphylococcus aureus. Fungal pathogens included Cryptococcus neoformans and Candida albicans. The cyanoximates alone showed no antimicrobial impact, and the incorporation of the SbPh4 group enabled the antimicrobial effect. Overall, the new antimony compounds showed a strong potential as both broad- and narrow-spectrum antimicrobials against selected bacterial and fundal pathogens and provide insights for further synthetic modifications of the compounds to increase their activities.

  在室温下，利用固体 AgL（或 TlL）和 Sb(C6H5)4Br 在 CH3CN 中发生的高产异质偏合成反应，合成了一系列由 Sb( )4L 组成的八种新型有机锑(V)氰肟酸盐。氰肟酸 L 是根据其水溶性和以往的生物活性，从一大批 48 种已知肟类化合物中特别挑选出来的。合成的化合物在有机溶剂中的溶解性很好，并采用了多种常规光谱和物理方法对其进行了研究。测定了所有报告的有机金属化合物的晶体结构，发现锑原子形成了扭曲的三叉双锥环境，酸配体通过肟基团的 O 原子形成了单齿轴结合。这些化合物在固态和溶液分子化合物中都具有热稳定性。研究人员首次将这一系列专门设计的有机锑（V）化合物作为潜在的非抗生素抗菌剂，用于对抗三种细菌性和两种真菌性人类病原体。细菌病原体包括革兰氏阴性大肠杆菌和绿脓杆菌，以及革兰氏阳性金黄色葡萄球菌。真菌病原体包括新生隐球菌和白色念珠菌。单独的氰基亚胺没有抗菌效果，加入 SbPh4 基团后才有抗菌效果。总之，这些新的锑化合物显示出作为广谱和窄谱抗菌剂对付某些细菌和基底病原体的强大潜力，并为进一步合成修饰这些化合物以提高其活性提供了启示。
• Part 1: Experimental and theoretical studies of 2-cyano-2-isonitroso-N-piperidynylacetamide (HPiPCO), 2-cyano-2-isonitroso-N-morpholylacetamide (HMCO) and their Pt- and Pd-complexes
  作者：Jessica Ratcliff、Janina Kuduk-Jaworska、Henryk Chojnacki、Victor Nemykin、Nikolay Gerasimchuk

  DOI：10.1016/j.ica.2011.12.005

  日期：2012.4

  The reaction between substituted cyan-acetamides NC-CH2-C(O) X (X = N-piperidyne or N-morpholyl residues) and gaseous methylnitrite CH3ONO in isopropanol at room temperature in the presence of a base within minutes leads to colorless cyanoximes 2-cyano-2-isonitroso-N-piperidynylacetamide (further as HPiPCO), and 2-cyano-2-isonitroso-N-morpholylacetamide (HMCO) in 70-90% yield. The deprotonation of HPiPCO and HMCO with a base such as NaOEt affords anionic Na-salts, bright-yellow in color originated from n -> pi* transitions in the nitroso-chromophore. Anionic cyanoximates react with aqueous solutions of K2MCl4 (M = Pd, Pt) to form yellow-orange PdL2 and dark blue-green polymeric [PtL2](n) (L = PiPCO, MCO), which upon treatment with DMSO or DMF breaks down to pale-yellow monomeric PtL2. Synthesized metal complexes were characterized by spectroscopic methods (IR, UV-Vis), measurement of the electric conductivity and the X-ray analysis. Both PdL2 and PtL2 exhibit non-electrolyte behavior in DMSO and DMF. Crystal structures of Pd(PiPCO)(2) and Pt(PiPCO)(2) were determined and revealed the formation of the cis-complexes with nearly planar geometry around the metal core and an adoption of the cis-anti configuration by anions, in contrast to the trans-anti geometry in structures of uncomplexed HPiPCO and HMCO. Ab initio calculations were performed for all six compounds: two cyanoxime ligands and four Pd and Pt metal complexes. A very satisfactory agreement between the calculated and experimental values of geometrical parameters of all evaluated compounds was attained. The electron densities, energies of HOMO and LUMO orbitals and molecular electrostatic potentials were calculated as well. (C) 2011 Elsevier B. V. All rights reserved.