p-尼可地尔 | 65141-47-1

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: p-尼可地尔
• 中文别名: P-尼可地尔
• 英文名称: N-(2-nitroxyethyl)isonicotinamide
• 英文别名: 2-(isonicotinamido)ethyl nitrate；para-nicorandil；p-nicorandil；4-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]-；2-(pyridine-4-carbonylamino)ethyl nitrate
• CAS: 65141-47-1
• 化学式: C₈H₉N₃O₄
• 分子量: 211.177
• InChiKey: VZCYAIHIDPPQHC-UHFFFAOYSA-N

物化性质

• 熔点：
  109-111°C
• 沸点：
  456.7±25.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• WGK Germany：
  1
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  p-尼可地尔 生成 Nitric acid;2-(pyridine-4-carbonylamino)ethyl nitrate
  参考文献：
  名称：

  NAGANO, HIROYUKI;MORI, TAKASHI;TAKAKU, SAKAE;MATSUNAGA, ISAO;KUJIRAI, TAT+

  摘要：

  DOI：
• 作为产物：
  描述：

  异烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 p-尼可地尔
  参考文献：
  名称：

  摘要：

  Previously unknown N-(2-nitroxyethyl)isonicotinamide was synthesized by the reaction of isonicotinoyl chloride with 2-nitroxyethylamine and was used as a ligand in the reactions with PdCl2 and PtCl2 to prepare new complexes, viz., trans-bis[(2-nitroxyethyl)isonicotinamide-N]dichloropalladium(ii) and cis-bis[(2-nitroxyethyl)isonicotinamide-N]dichloroplatinum(II), respectively. The structures of the ligand and the resulting complexes were established by X-ray diffraction analysis.

  DOI：

  10.1023/a:1011385913110

文献信息

• Highly efficient synthesis of β-nitrate ester carboxamides through the ring-opening of 2-oxazolines
  作者：Kai Qiao、Xin Yuan、Li Wan、Ming-Wei Zheng、Dong Zhang、Bing-Bing Fan、Zhe-Chen Di、Zheng Fang、Kai Guo

  DOI：10.1039/c7gc02682j

  日期：——

  A novel method for the synthesis of β-nitrate ester carboxamides using non-corrosive tert-butyl nitrite (TBN) as the nitro source and easily available oxygen as the oxidant has been developed. Variously substituted 2-oxazolines were efficiently ring-opened to deliver the corresponding products in excellent yields. Notably, this reaction provides fast access to pharmaceuticals such as nicorandil.

  已经开发出一种新的合成方法，该方法使用非腐蚀性的亚硝酸叔丁酯（TBN）作为硝基源，并利用易获得的氧气作为氧化剂来合成β-硝酸酯羧酰胺。有效地开环了各种取代的2-恶唑啉，以优异的产率递送相应的产物。值得注意的是，该反应提供了对药物如尼可地尔的快速访问。
• Synthesis, antinociceptive activity and pharmacokinetic profiles of nicorandil and its isomers
  作者：Isabela C. César、Adriana M. Godin、Débora P. Araujo、Francinely C. Oliveira、Raquel R. Menezes、Julliana R.A. Santos、Mariana O. Almeida、Marcela M.G.B. Dutra、Daniel A. Santos、Renes R. Machado、Gerson A. Pianetti、Márcio M. Coelho、Ângelo de Fátima

  DOI：10.1016/j.bmc.2014.03.011

  日期：2014.5

  suggested to mediate its vasodilator activity. We synthesized nicorandil and its two isomers, which vary in the positions of the side chain containing the nitric oxide (NO) donor, and also their corresponding denitrated metabolites. The activities of these compounds were evaluated in an experimental model of pain in mice. Pharmacokinetic parameters of nicorandil and its isomers, as well as the plasma

  尼古拉地尔（N-（2-羟乙基）烟酰胺硝酸盐）是一种抗心绞痛药物，可激活鸟苷酸环化酶并打开ATP依赖的K +通道，这些作用被认为可介导其血管舒张活性。我们合成了尼可地尔及其两个异构体，它们在含有一氧化氮（NO）供体的侧链位置以及相应的脱硝代谢产物上也有所不同。在小鼠的疼痛实验模型中评估了这些化合物的活性。测定了尼可地尔及其异构体的药代动力学参数，以及相应的脱硝代谢产物以及烟酰胺和亚硝酸盐的血浆浓度。尼古兰地表现出最高的抗伤害感受活性，而邻位-异构体活性最低。诱导较高血浆亚硝酸盐浓度的尼古拉地和对尼古拉地尼具有较高的抗伤害感受活性，这表明NO的释放可能介导了该活性。
• New method for the synthesis of metal complexes based on PtIV and substituted nicotinamides and isonicotinamides and investigation of their antimetastatic activity
  作者：B. S. Fedorov、M. A. Fadeev、G. I. Kozub、A. N. Chekhlov、N. P. Konovalova、T. E. Sashenkova、E. N. Berseneva、O. V. Dobrokhotova、L. V. Tatyanenko

  DOI：10.1007/s11172-011-0186-8

  日期：2011.6

  Complexes of platinum tetrachloride with substituted nicotinamides and isonicotinamides were synthesized by the reactions of the corresponding amides with hexachloroplatinic acid. All these complexes are low-toxic. The strong antimetastatic activity of these complexes against Lewis lung carcinoma and B16 melanoma experimental tumors was found in an enzyme system and was then shown in experiments on animals.

  通过相应的酰胺与六氯铂酸的反应合成了四氯化铂与取代烟酰胺和异烟酰胺的配合物。所有这些复合物都是低毒的。在酶系统中发现了这些复合物对 Lewis 肺癌和 B16 黑色素瘤实验性肿瘤的强抗转移活性，并在动物实验中得到了证明。
• ——
  作者：B. S. Fedorov、N. I. Golovina、M. A. Fadeev、G. V. Strukov、V. V. Kedrov、G. V. Shilov、G. N. Boiko、L. O. Atovmyan

  DOI：10.1023/a:1011385913110

  日期：——

  Previously unknown N-(2-nitroxyethyl)isonicotinamide was synthesized by the reaction of isonicotinoyl chloride with 2-nitroxyethylamine and was used as a ligand in the reactions with PdCl2 and PtCl2 to prepare new complexes, viz., trans-bis[(2-nitroxyethyl)isonicotinamide-N]dichloropalladium(ii) and cis-bis[(2-nitroxyethyl)isonicotinamide-N]dichloroplatinum(II), respectively. The structures of the ligand and the resulting complexes were established by X-ray diffraction analysis.
• NAGANO, HIROYUKI;MORI, TAKASHI;TAKAKU, SAKAE;MATSUNAGA, ISAO;KUJIRAI, TAT+
  作者：NAGANO, HIROYUKI、MORI, TAKASHI、TAKAKU, SAKAE、MATSUNAGA, ISAO、KUJIRAI, TAT+

  DOI：——

  日期：——