indole-2-carboxaldehyde oxime | 881853-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: indole-2-carboxaldehyde oxime
• 英文别名: indol-2-carbaldoxime；1H-indole-2-carbaldehyde oxime；N-Hydroxy-1-(2H-indol-2-ylidene)methanamine；N-(1H-indol-2-ylmethylidene)hydroxylamine
• CAS: 881853-73-2
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: HUCZEGXARCIQHC-UHFFFAOYSA-N

物化性质

• 熔点：
  143-145 °C(Solv: ethanol (64-17-5))
• 沸点：
  359.5±15.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  indole-2-carboxaldehyde oxime 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 1-(1H-吲哚-2-基)甲胺
  参考文献：
  名称：

  前所未有的化学结构和仿生合成的芥蓝素，一种来自野生十字花科植物金缕梅的植物抗毒素。

  摘要：

  描述了芥蓝素的分离，结构测定，总合成和抗真菌活性。芥蓝素是野生十字花科狗芥菜产生的一种新型植物抗毒素。芥蓝素是一种结构独特的植物生物碱，代表螺[2H-吲哚-2,5'（4'H）-噻唑] -3-one的第一个实例，可能源自C-3-C-2碳迁移在3-取代的吲哚基核中。

  DOI：

  10.1039/b515331j
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以99%的产率得到indole-2-carboxaldehyde oxime
  参考文献：
  名称：

  前所未有的化学结构和仿生合成的芥蓝素，一种来自野生十字花科植物金缕梅的植物抗毒素。

  摘要：

  描述了芥蓝素的分离，结构测定，总合成和抗真菌活性。芥蓝素是野生十字花科狗芥菜产生的一种新型植物抗毒素。芥蓝素是一种结构独特的植物生物碱，代表螺[2H-吲哚-2,5'（4'H）-噻唑] -3-one的第一个实例，可能源自C-3-C-2碳迁移在3-取代的吲哚基核中。

  DOI：

  10.1039/b515331j

文献信息

• [EN] SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] COMPOSÉS SPIRO-OXADIAZOLINE EN TANT QU'AGONISTES DES RÉCEPTEURS DE L'ACÉTYLCHOLINE Α-7 NICOTINIQUE
  申请人：FORUM PHARMACEUTICALS INC

  公开号：WO2015066371A1

  公开（公告）日：2015-05-07

  The present invention relates to novel spiro-oxadiazoline compounds that are suitable as agonists or partial agonists of a7-nAChR, and pharmaceutical compositions of the same, methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering a spiro-oxadiazoline cx7-nAChR agonist or partial agonist, to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

  本发明涉及新型螺环-噁二唑啉化合物，适用作a7-nAChR的激动剂或部分激动剂，以及这些化合物和组合物的制备方法、药物组合物，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物。具体而言，涉及向需要的患者（例如患有认知缺陷和/或希望增强认知功能的患者）施用螺环-噁二唑啉cx7-nAChR激动剂或部分激动剂的方法，以使其获益。
• Design, Synthesis and Molecular Docking Studies of Novel Indole–Isoxazole–Triazole Conjugates as Potent Antibacterial Agents
  作者：M. Prashanthi、H. Ramesh Babu、Janapatla Uma Rani

  DOI：10.1134/s1068162021020217

  日期：2021.3

  vitroantibacterial activity. 5-((3-Chlorophenoxy)methyl)-3-(1-((1-(3-(trifluoromethyl)phenyl)-1 H -1,2,3-triazol-4-yl)methyl)-1 H -indol-2-yl)isoxazole ( VId ) showed more potent activity against B. subtilis and S. aureus , whereas, the compound 5-((3-chlorophenoxy)methyl)-3-(1-((1-(3,5-dichlorophenyl)-1 H -1,2,3-triazol-4-yl) methyl)-1 H -indol-2-yl)isoxazole ( VIb )showed potent activity against S. aureus when compared

  摘要 为寻找更好的抗菌剂，一系列新型5-((芳基)甲基)-3-(1 H-吲哚-2-基)异恶唑(IIIa-e)和5-((3-氯苯氧基)甲基) -3-(1-((1-(芳基)-1 H -1,2,3-triazol-4-yl)methyl)-1 H-indol-2-yl)isoxazole (VIa – e) 合成于一锅法使用吲哚-2-甲醛（I）、取代（prop-2-yn-1-yloxy）苯和不同的取代1-叠氮苯（V），进一步评估了它们的体外抗菌活性。5-((3-氯苯氧基)甲基)-3-(1-((1-(3-(三氟甲基)苯基)-1 H -1,2,3-三唑-4-基)甲基)-1 H - indol-2-yl)isoxazole (VId) 对枯草芽孢杆菌和金黄色葡萄球菌表现出更强的活性，而化合物 5-((3-氯苯氧基)甲基)-3-(1-((1-(3, 5-二氯苯基)-1 H -1,2,3-三唑-4-基)甲基)-1
• Synthesis of heterocyclic N-(β-d-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase
  作者：Bálint Kónya、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2012.01.020

  日期：2012.4

  In a DCC-mediated coupling 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine and propiolic acid gave N-propynoyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine which was transformed by 1,3-dipolar cycloadditions with aromatic azides and nitrile-oxides to the corresponding O-peracetylated N-(beta-D-glucopyranosyl)-1-substituted-1,2,3-triazole-4-carboxamides and N-(beta-D-glucopyranosyl)-3-substitutedisoxazole-5-carboxamides, respectively. These compounds were O-deacetylated by Zemplen's protocol to be tested as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitors of the two series were N-(beta-D-glucopyranosyl)-1-(3,5-dimethyl-phenyl)-1,2,3-triazole-4-carboxamide (K-i = 34 mu M) and N-(beta-D-glucopyranosyl)-3-(indol-2-yl)-isoxazole-5-carboxamide (K-i = 164 mu M). (C) 2012 Elsevier Ltd. All rights reserved.
• Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition
  作者：David Goyard、Bálint Kónya、Aikaterini S. Chajistamatiou、Evangelia D. Chrysina、Jérémy Leroy、Sophie Balzarin、Michel Tournier、Didier Tousch、Pierre Petit、Cédric Duret、Patrick Maurel、László Somsák、Tibor Docsa、Pál Gergely、Jean-Pierre Praly、Jacqueline Azay-Milhau、Sébastien Vidal

  DOI：10.1016/j.ejmech.2015.12.004

  日期：2016.1

  Glycogen phosphorylase (GP) is a target for the treatment of hyperglycaemia in the context of type 2 diabetes. This enzyme is responsible for the depolymerization of glycogen into glucose thereby affecting the levels of glucose in the blood stream. Twelve new D-glucopyranosylidene-spiro-isoxazolines have been prepared from O-peracylated exo-D-glucals by regio- and stereoselective 1,3-dipolar cycloaddition of nitrile oxides generated in situ by treatment of the corresponding oximes with bleach. This mild and direct procedure appeared to be applicable to a broad range of substrates. The corresponding 0-unprotected spiro-isoxazolines were evaluated as glycogen phosphorylase (GP) inhibitors and exhibited IC50 values ranging from 1 to 800 mu M. Selected inhibitors were further evaluated in vitro using rat and human hepatocytes and exhibited significant inhibitory properties in the primary cell culture. Interestingly, when tested with human hepatocytes, the tetra-O-acetylated spiro-isoxazoline bearing a 2-naphthyl residue showed a much lower IC50 value (2.5 mu M), compared to that of the 0-unprotected analog (19.95 mu M). The most promising compounds were investigated in Zucker fa/fa rat model in acute and sub-chronic assays and decreased hepatic glucose production, which is known to be elevated in type 2 diabetes. This indicates that glucose-based spiro-isoxazolines can be considered as anti-hyperglycemic agents in the context of type 2 diabetes. (C) 2015 Elsevier Masson SAS. All rights reserved.