2-oximino-2-cyano-N-pyrrolidine acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-oximino-2-cyano-N-pyrrolidine acetamide
• 英文别名: 2-Hydroxyimino-3-oxo-3-pyrrolidin-1-ylpropanenitrile；2-hydroxyimino-3-oxo-3-pyrrolidin-1-ylpropanenitrile
• 化学式: C₇H₉N₃O₂
• 分子量: 167.167
• InChiKey: KIAPCJYRDMTWQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium tetrachloropalladate(II) 、 2-oximino-2-cyano-N-pyrrolidine acetamide 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  New in vitro highly cytotoxic platinum and palladium cyanoximates with minimal side effects in vivo

  摘要：

  Several biologically active bivalent Pd and Pt complexes with two structurally similar cyanoxime ligands abbreviated as H(DECO): 2-oximino-2-cyano-N,N'-diethylacetamide, and H(PyrCO): 2-oximino-2-cyan-N-pyrrolidine acetamide were synthesized and characterized using spectroscopic methods, thermal analysis and X-ray crystallography. Structures revealed planar cis-geometry of studied complexes. Freshly obtained Pt(DECO)(2) , Pd (DECO)(2), Pt(PyrCO)(2) and Pd(PyrCO)(2) complexes were used in for in vitro cytotoxicity assays using two different etiology human cancer cell lines HeLa and WiDr cells. Investigated compounds showed cytotoxicity levels at or above cisplatin. Pt(DECO)(2) was also tested in vivo in healthy C57BL/6 mice. The complex was administered at three different dosage (0, 7.5, 15 mg/kg, i.p. once/week), over a total period of 8 weeks. No changes were observed in the animal weight in the treated mice compared to the control dextrose-treated group. The levels of erythrocytes, leukocytes, and hemoglobin were within the normal level suggesting low myelotoxicity. Negligible cardiotoxicity was observed from the histological evaluation of the hearts from the treated animals. Results from the tail nerve conduction velocity (NCV) and nerve histomorphometry suggested no impact of Pt(DECO)(2) on peripheral nerves. The complex, however, induced certain hepatotoxicity and lead to the elevation of IL-6, a pro-inflammatory cytokine. Overall, Pt(DECO)(2) showed minimal in vivo toxicity, thus presenting a promising candidate for future testing in animal models of cancer.

  DOI：

  10.1016/j.jinorgbio.2020.111082
• 作为产物：
  描述：

  1-(氰基乙酰基)吡咯烷 在 硝基甲烷 、 sodium n-propoxide 作用下， 以 丙醇 为溶剂， 生成 2-oximino-2-cyano-N-pyrrolidine acetamide
  参考文献：
  名称：

  New in vitro highly cytotoxic platinum and palladium cyanoximates with minimal side effects in vivo

  摘要：

  Several biologically active bivalent Pd and Pt complexes with two structurally similar cyanoxime ligands abbreviated as H(DECO): 2-oximino-2-cyano-N,N'-diethylacetamide, and H(PyrCO): 2-oximino-2-cyan-N-pyrrolidine acetamide were synthesized and characterized using spectroscopic methods, thermal analysis and X-ray crystallography. Structures revealed planar cis-geometry of studied complexes. Freshly obtained Pt(DECO)(2) , Pd (DECO)(2), Pt(PyrCO)(2) and Pd(PyrCO)(2) complexes were used in for in vitro cytotoxicity assays using two different etiology human cancer cell lines HeLa and WiDr cells. Investigated compounds showed cytotoxicity levels at or above cisplatin. Pt(DECO)(2) was also tested in vivo in healthy C57BL/6 mice. The complex was administered at three different dosage (0, 7.5, 15 mg/kg, i.p. once/week), over a total period of 8 weeks. No changes were observed in the animal weight in the treated mice compared to the control dextrose-treated group. The levels of erythrocytes, leukocytes, and hemoglobin were within the normal level suggesting low myelotoxicity. Negligible cardiotoxicity was observed from the histological evaluation of the hearts from the treated animals. Results from the tail nerve conduction velocity (NCV) and nerve histomorphometry suggested no impact of Pt(DECO)(2) on peripheral nerves. The complex, however, induced certain hepatotoxicity and lead to the elevation of IL-6, a pro-inflammatory cytokine. Overall, Pt(DECO)(2) showed minimal in vivo toxicity, thus presenting a promising candidate for future testing in animal models of cancer.

  DOI：

  10.1016/j.jinorgbio.2020.111082

文献信息

• Nickel(II) Aqua Complexes with Chelating Ligands: What Happens When Water Is Gone?
  作者：Adedamola A. Opalade、Imre Labadi、Carlos Gomez-Garcia、Oleksandr Hietsoi、Nikolay Gerasimchuk

  DOI：10.1021/acs.cgd.2c00717

  日期：2022.10.5

  have [NiL2(H2O)2] composition with an axial position of coordinated water molecules and trans-geometry of the Ni(II) center, surrounded by two deprotonated cyanoxime anions forming five-membered chelate rings. Based on thermal analysis profiles, the hydrated complexes were dehydrated, and structural changes were investigated by spectroscopic magnetochemistry methods and X-ray analysis. The measurements

  与 2-氰基-2-羟基亚氨基-乙酰胺 ( HACO )、羟基亚氨基-吡啶-2-基-乙腈 ( H2PCO )、2-氰基-2-羟基亚氨基乙酸乙酯 ( HECO )形成的一系列水合 Ni(II) 离子络合物, 2-羟基亚氨基-3-氧代-3-哌啶-1-基丙腈 ( HPiPCO ) 和 2-氰基-2-羟基亚氨基-N-吡咯烷-乙酰胺 ( HPyrCO ) 配体被合成并表征为无水 Ni( II) 配位聚合物。所有这些配合物都有 [NiL 2 (H 2 O) 2] 组成具有配位水分子的轴向位置和 Ni(II) 中心的反几何形状，被两个去质子化氰肟阴离子包围，形成五元螯合环。基于热分析曲线，水合配合物被脱水，并通过光谱磁化学方法和 X 射线分析研究结构变化。测量结果表明复合物在脱水后发生重排，从而形成肟基-μ 2的聚合物链-桥接的镍 (II) 配合物。在此过程中观察到显着的颜色变化。因此，在所有情况下，都观察到具有反铁磁耦合
• Remarkable Structural Diversity of N-Pyrrolidine-cyanoxime and its Ni(II) Complexes
  作者：Adedamola Abraham Opalade、Nikolay Gerasimchuk、Oleksandr Hietsoi、Olga Gerasimchuk

  DOI：10.1021/acs.cgd.4c00496

  日期：2024.7.3

  the same system after filtration of the main product and subsequent crystallization of new products from the mother liquor. These were RED, the main product [Ni(PyrCO)2(H2O)2](H2O), and two differently colored polymorphs GREEN [Ni(PyrCO)2(H2O)2] and VIOLET [Ni(PyrCO)2(H2O)2], with only minor amounts of the fac-Na[Ni(PyrCO)3] tris-cyanoximate. Two other complexes, dimeric [Ni2(PyrCO)4(H2O)2]·2C3H7OH

  合成了一种新型氰肟，2-肟基-2-氰基-N-吡咯烷-乙酰胺（又称为HPyrCO），并通过光谱方法、热分析和X射线晶体学对其进行了表征。该结构揭示了八个独立的分子，在不对称单元中具有复杂的分子间氢键，并采用了氰肟的反式构型。此后，从水溶液中获得了一系列Ni(II)配位化合物、结晶水合物，以及这种新型氰肟，在过滤主产物并随后从母液中结晶出新产物后，从同一系统中分离出四种配合物。这些是红色，主要产物[Ni(PyrCO) 2 (H 2 O) 2 ](H 2 O)，以及两种不同颜色的多晶型物绿色 [Ni(PyrCO) 2 (H 2 O) 2 ] 和紫色 [Ni(PyrCO) 2 (H 2 O) 2 ]，仅含有少量的 fac-Na[Ni(PyrCO) 3 ] 三氰肟酯。另外两个配合物，二聚体 [Ni 2 (PyrCO) 4 (H 2 O) 2 ]·2C 3 OH和三氰肟酯[NiHPyrCO}(PyrCO)