N-亚硝基-1,2,3,6-四氢吡啶 | 55556-92-8

• 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: N-亚硝基-1,2,3,6-四氢吡啶
• 英文名称: N-nitroso-1,2,3,6-tetrahydropyridine
• 英文别名: 1-nitroso-1,2,3,6-tetrahydro-pyridine；1-Nitroso-1,2,3,6-tetrahydropyridine；N-Nitroso-1,2,3,6-tetrahydropyridin；3,4-Dehydro-1-nitrosopiperidin；1-nitroso-3,6-dihydro-2H-pyridine
• CAS: 55556-92-8
• 化学式: C₅H₈N₂O
• mdl: MFCD01691504
• 分子量: 112.131
• InChiKey: KIUHZRUPPGAVPY-UHFFFAOYSA-N

物化性质

• 沸点：
  210.05°C (rough estimate)
• 密度：
  1.1524 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-亚硝基-1,2,3,6-四氢吡啶 以67%的产率得到
  参考文献：
  名称：

  SAAVEDRA J. E., J. ORG. CHEM., 1979, 44, NO 25, 4516-4518

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 sodium chloride 、 碳酸氢钠 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 N-亚硝基-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Pyrazole-3-carboxamide derivatives, process for their preparation and

  摘要：

  本发明涉及一种新型的吡唑-3-羧酰胺衍生物，其化学式为##STR1##其中取代基如规范中定义。本发明还涉及一种制备这些新型衍生物的方法，以及它们存在的药物组合物。

  公开号：

  US05462960A1

文献信息

• Pyrazole-3-carboxamide derivatives, process for their preparation and
  申请人：Sanofi

  公开号：US05462960A1

  公开（公告）日：1995-10-31

  The present invention relates to novel pyrazole-3-carboxamide derivatives of the formula ##STR1## in which the substituents are as defined in the specification. The present invention further relates to a process for the preparation of these novel derivatives and to the pharmaceutical compositions in which they are present.

  本发明涉及一种新型的吡唑-3-羧酰胺衍生物，其化学式为##STR1##其中取代基如规范中定义。本发明还涉及一种制备这些新型衍生物的方法，以及它们存在的药物组合物。
• KUPPER R.; MICHEJDA C. J., J. ORG. CHEM, 1979, 44, NO 13, 2326-2328
  作者：KUPPER R.、 MICHEJDA C. J.

  DOI：——

  日期：——
• LYLE, R. E.;KRUEGER, W. E.;GUNN, V. E., J. ORG. CHEM., 1983, 48, N 20, 3574-3575
  作者：LYLE, R. E.、KRUEGER, W. E.、GUNN, V. E.

  DOI：——

  日期：——
• Oxidation of nitrosamines. 2. Conversion of N-nitroso-1,2,3,6-tetrahydropyridine, via the epoxide, to N-nitroso-4-hydroxy-1,2,3,4-tetrahydropyridine
  作者：Jose E. Saavedra

  DOI：10.1021/jo00393a012

  日期：1979.12
• Synthesis of new 4-[2-(4-methyl(amino)sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines: A search for novel nitric oxide donor anti-inflammatory agents
  作者：Morshed Alam Chowdhury、Khaled R.A. Abdellatif、Ying Dong、Edward E. Knaus

  DOI：10.1016/j.bmc.2008.08.059

  日期：2008.10

  A group of 4-[2-(4-methyl(amino) sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (11-14) possessing a variety of substituents (Me, CO2Et, H, N = O) attached to the 1,2,3,6-tetrahydropyridyl N-1-nitrogen atom were synthesized and evaluated as anti-inflammatory agents. Structure-activity relationship data showed that the N-methyl-1,2,3,6-tetrahydropyridylmoiety is a suitable bioisosteric replacement for the tolyl moiety in celecoxib. The most potent compound 4-[5-(1-methyl- 1,2,3,6-tetrahydropyridin-4-yl)-3-trifluoromethylpyrazol-1-yl]benzenesulfonamide (11b; ED50 = 61.2 mg/kg po) exhibited an anti-inflammatory activity between that of the reference drugs celecoxib (ED50 = 10.8 mg/kg po) and aspirin (ED50 = 128.7 mg/kg po). The synthesis of model hybrid nitric oxide donor N-diazen-1-ium-1,2-diolate derivatives of 4-[2-(4-methyl(amino) sulfonylphenyl)-5-trifluoromethyl-2H- pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (5) requires further investigation since the reaction of 1,2,3,6-tetrahydropyridines with nitric oxide furnished the undesired N-nitroso-1,2,3,6-tetrahydrohydropyridyl product rather than the desired N-diazen-1-ium-1,2-diolate-1,2,3,6-tetrahydropyridyl product. (C) 2008 Elsevier Ltd. All rights reserved.