(Z)-2-cyclopropyl-N-hydroxyacetimidamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-2-cyclopropyl-N-hydroxyacetimidamide
• 英文别名: 2-cyclopropylacetamide oxime；cyclopropylacetamide oxime；2-cyclopropyl-N'-hydroxyethanimidamide
• 化学式: C₅H₁₀N₂O
• mdl: MFCD12138806
• 分子量: 114.147
• InChiKey: DXMRZDCNKSWOHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氢溴酸槟榔碱 、 (Z)-2-cyclopropyl-N-hydroxyacetimidamide 在 4 A molecular sieve 、 sodium 作用下， 生成 3-(cyclopropylmethyl)-5-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Muscarinic cholinergic agonists and antagonists of the 3-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydropyridine type. Synthesis and structure-activity relationships

  摘要：

  A series of 3-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydro-1-methylpyridines (2a-q) were synthesized and tested for central muscarinic cholinergic receptor binding affinity by using [H-3]oxotremorine-M and [H-3]QNB as ligands and in a functional assay using guinea pig ileum. The analogues with unbranched C1-8-alkyl substituents (2a-g) were agonist, whereas the compounds with branched or cyclic substituents (2h-m) were antagonists. The alkyl ether analogues (2o-q) were also agonists but had lower receptor binding affinity than the corresponding alkyl analogues. The 3-(5-alkyl-1,2,4-oxadiazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine analogues had only very low affinity for the central muscarinic receptors and were weak antagonists in the ileum assay. A few 3-(3-butyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydro-1-methylpyridines substituted with methyl or hydrogen in the 1-, 5-, or 6-position were synthesized and tested. N-Desmethyl analogue 7 was a potent muscarinic agonist, whereas N-desmethyl-5-methyl analogue 11 and N-methyl-6-methyl analogue 13 both were antagonists with lower muscarinic receptor affinity. The 3-(3-butyl-1,2,4-oxadiazol-5-yl)quinuclidine (17) and tropane (15) analogues were both very potent antagonists with high affinity for central muscarinic receptors. The ratio [IC50(QNB)/IC50(Oxo-M)] x 0.162 proved to be a good indicator of the efficacy of the compounds in the guinea pig ileum assay.

  DOI：

  10.1021/jm00106a033
• 作为产物：
  描述：

  环丙乙腈 在 羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 (Z)-2-cyclopropyl-N-hydroxyacetimidamide
  参考文献：
  名称：

  氯化铁 (III) 催化高效合成 2-取代的喹唑啉-4(3H)-酮

  摘要：

  开发了一种简单高效的 2-取代喹唑啉-4(3 H)-酮的合成方法，通过氯化铁 (III) 催化的靛红酸酐与各种胺肟衍生物的反应。筛选了几种芳基和烷基酰胺肟以证明该方法的范围。

  DOI：

  10.1055/s-0033-1340786

文献信息

• [EN] IMIDAZOPYRROLOPYRIDINE AS INHIBITORS OF THE JAK FAMILY OF KINASES<br/>[FR] IMIDAZOPYRROLOPYRIDINE EN TANT QU'INHIBITEURS DE LA FAMILLE JAK DE KINASES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2018112382A1

  公开（公告）日：2018-06-21

  2-((1r,4r)-4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexyl)acetonitrile compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions mediated by JAK, such as inflammatory bowel disease.

  2-((1r,4r)-4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexyl)acetonitrile化合物，含有它们的药物组合物，制备它们的方法，以及使用它们的方法，包括用于治疗由JAK介导的疾病状态、紊乱和疾病，如炎症性肠病的方法。
• [EN] OXADIAZOLE COMPOUNDS<br/>[FR] COMPOSÉS D'OXADIAZOLE
  申请人：REMYND NV

  公开号：WO2015140130A1

  公开（公告）日：2015-09-24

  The present invention relates to a compound of formula (I) or (II) or a stereoisomer, enantiomer, racemic, or tautomer thereof, (I) (II) wherein R1,R2,R3,L1,L2,L3,L4,L5 and n, have the same meaning as that defined in the claims and the description. The present invention also relates to compositions, in particular pharmaceuticals, comprising such compounds, and to uses of such compounds and compositions for the prevention and/or treatment of metabolic disorders and/or neurodegenerative diseases, and/or protein misfolding disorders.

  本发明涉及式(I)或(II)的化合物或其立体异构体、对映体、消旋体或互变异构体，其中R1、R2、R3、L1、L2、L3、L4、L5和n的含义与权利要求和说明中定义的含义相同。本发明还涉及包含这些化合物的组合物，特别是药物，以及利用这些化合物和组合物预防和/或治疗代谢紊乱和/或神经退行性疾病和/或蛋白质错折性疾病的用途。
• Bioisosteric replacement of the pyrazole 3-carboxamide moiety of rimonabant. A novel series of oxadiazoles as CB1 cannabinoid receptor antagonists
  作者：Cheng-Ming Chu、Ming-Shiu Hung、Min-Tsang Hsieh、Chun-Wei Kuo、Suja T. D.、Jen-Shin Song、Hua-Hao Chiu、Yu-Sheng Chao、Kak-Shan Shia

  DOI：10.1039/b807648k

  日期：——

  Based on the bioisosteric replacement of the pyrazole C3-carboxamide of rimonabant with a 5-alkyl oxadiazole ring, a novel class of oxadiazole derivatives with promising biological activity towards CB1 receptors was discovered. Among them, compounds with an alkyl linker containing a strong electron-withdrawing group (e.g., CF3) and a sterically favorable bulky group (e.g., t-butyl) exhibited excellent CB1 antagonism and selectivity, and thus might serve as potential candidates for further development as anti-obesity agents.

  基于利莫那班的吡唑C3-酰胺的生物等排替换为五元氧二氮杂环，发现了一类新型氧二氮杂环衍生物，具有有希望的生物活性，对CB1受体具有活性。其中，含有强吸电子基团（例如，CF3）和立体有利的大体积基团（例如，叔丁基）的烷基链路的化合物表现出优异的CB1拮抗作用和选择性，因此可能作为进一步开发为抗肥胖药物的潜在候选。
• N-(aryl/heteroaryl) amino acid esters, pharmaceutical compositions
  申请人：Athena Neurosciences, Inc.

  公开号：US05965614A1

  公开（公告）日：1999-10-12

  Disclosed are compounds which inhibit .beta.-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits .beta.-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  揭示了一种抑制β-淀粉样肽释放和/或合成的化合物，因此，对治疗阿尔茨海默病具有实用价值。还揭示了包括抑制β-淀粉样肽释放和/或合成的化合物的药物组合物，以及使用这种药物组合物预防性和治疗性治疗阿尔茨海默病的方法。
• One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate
  作者：Kande K.D. Amarasinghe、Matthew B. Maier、Anil Srivastava、Jeffrey L. Gray

  DOI：10.1016/j.tetlet.2006.03.155

  日期：2006.5

  A convenient one-pot synthesis of 1,2,4-oxadiazoles is described. The condensation of carboxylic acid esters and amidoximes in the presence of potassium carbonate was employed to synthesize a variety of mono-, bis- and tris-oxadiazoles in moderate to excellent yields.

  描述了一种方便的一锅合成1,2,4-恶二唑。在碳酸钾存在下，羧酸酯和and胺肟的缩合反应以中等至极好的收率合成了各种单，双和三恶二唑。