N′-hydroxy-3-iodobenzenecarboximidamide | 453565-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N′-hydroxy-3-iodobenzenecarboximidamide
• 英文别名: Benzenecarboximidamide, N-hydroxy-3-iodo-；N'-hydroxy-3-iodobenzenecarboximidamide
• CAS: 453565-59-8
• 化学式: C₇H₇IN₂O
• 分子量: 262.05
• InChiKey: ZJZWHLKOOXUKIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  N′-hydroxy-3-iodobenzenecarboximidamide 在 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 12.33h， 生成 3-(3-iodophenyl)-5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazole methiodide
  参考文献：
  名称：

  Novel 5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazoles to investigate the activation of the α7 nicotinic acetylcholine receptor subtype: Synthesis and electrophysiological evaluation

  摘要：

  alpha 7 nicotinic acetylcholine receptors (nAChRs) are relevant therapeutic targets for a variety of disorders alpha including neurodegeneration, cognitive impairment, and inflammation. Although traditionally identified as an ionotropic receptor, the alpha 7 subtype showed metabotropic-like functions, mainly linked to the modulation of immune responses. In the present work, we investigated the structure-activity relationships in a set of novel alpha 7 ligands incorporating the 5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazole scaffold, i.e. derivatives 21a-34a and 21b-34b, aiming to identify the structural requirements able to preferentially trigger one of the two activation modes of this receptor subtype. The new compounds were characterized as partial and silent alpha 7 nAChR agonists in electrophysiological assays, which allowed to assess the contribution of the different groups towards the final pharmacological profile. Overall, modifications of the selected structural backbone mainly afforded partial agonists, among them tertiary bases 27a-33a, whereas additional hydrogen -bond acceptor groups in permanently charged ligands, such as 29b and 31b, favored a silent desensitizing profile at the alpha 7 nAChR. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.10.015
• 作为产物：
  描述：

  间碘苯腈 在 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 以95%的产率得到N′-hydroxy-3-iodobenzenecarboximidamide
  参考文献：
  名称：

  3-芳基-1,2,4-恶二唑酮及其类似物的多功能固相合成

  摘要：

  我们在这里报告了第一种装载酸性杂环化合物的方法（1,2,4-恶二唑-5-酮，1,2,4-恶二唑-5-硫酮和1,2,3,5-恶二唑-2-氧化物）在聚合物上。在Mitsunobu条件下，这些杂环被固定在4-羟甲基-3-甲氧基苯氧基丁酸苯甲基胺（HMPB-BHA）树脂上。多样化后，可以通过在稀释的TFA中进行简单处理来回收化合物。为了说明该方法的实用性，将碘代苯基衍生物固定在同一树脂上。HRMAS-NMR分析揭示了在Mitsunobu条件下这些杂环的反应性。随后使用Sonogashira偶联进行的多样化生产了新的（芳基乙炔基）-苯基-1,2,4-恶二唑-5-酮的小阵列。

  DOI：

  10.1016/j.tetlet.2006.12.050

文献信息

• Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
  申请人：——

  公开号：US20030055085A1

  公开（公告）日：2003-03-20

  The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.

  本发明提供了作为代谢型谷氨酸受体拮抗剂的化合物和药物组合物，用于治疗神经系统疾病和障碍。还公开了制备这些化合物的方法。
• [EN] 5-MEMBERED HETEROCYCLE-BASED P38 KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA KINASE P38 A BASE D'HETEROCYCLES A 5 CHAINONS
  申请人：TRIAD THERAPEUCTICS INC

  公开号：WO2005009973A1

  公开（公告）日：2005-02-03

  Provided are 5-membered heterocycle-based p38 kinase inhibitors. Further provided are pyrazole and imidazole-based p38 kinase, including p38α and p38β kinase, inhibitors. Pharmaceutical compositions containing the compounds are also provided. Methods of use of the compounds and compositions are also provided, including method of treatment, prevention, or amelioration of one or more symptoms of p38 kinase mediated diseases and disorders, including, but not limited to, inflammatory diseases and disorders.

  提供了基于5-成员杂环的p38激酶抑制剂。进一步提供了基于吡唑和咪唑的p38激酶抑制剂，包括p38α和p38β激酶。还提供了含有这些化合物的药物组合物。还提供了这些化合物和组合物的使用方法，包括治疗、预防或改善p38激酶介导的疾病和疾病的一个或多个症状的方法，包括但不限于炎症性疾病和疾病。
• [EN] BRIDGED BICYCLIC KALLIKREIN INHIBITORS<br/>[FR] INHIBITEURS BICYCLIQUES PONTÉS DE LA KALLIKRÉINE
  申请人：GLOBAL BLOOD THERAPEUTICS INC

  公开号：WO2016201052A1

  公开（公告）日：2016-12-15

  Provided herein are kallikrein modulating compounds, pharmaceutical compositions comprising the same, and uses thereof.

  本文提供了调节激肽酶的化合物、包含这些化合物的药物组合物，以及它们的用途。
• [EN] POLYHETEROCYCLIC COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES POLYHETEROCYCLIQUES ET UTILISATION DE CEUX-CI COMME ANTAGONISTES DU RECEPTEUR METABOTROPIQUE DU GLUTAMATE
  申请人：ASTRAZENECA AB

  公开号：WO2005080386A1

  公开（公告）日：2005-09-01

  The present invention relates to new compounds of formula (I), wherein P, Q, X1, X2, X3, X4, X5, X6, R1, R2, R3, m, n, and p are as defined as in formula (I), or salts, or hydrates thereof, processes for their preparation and new intermediates used in the preparation thereof, pharmaceutical compositions containing said compounds and to the use of said compounds in therapy.

  本发明涉及公式(I)的新化合物，其中P、Q、X1、X2、X3、X4、X5、X6、R1、R2、R3、m、n和p的定义如公式(I)中所述，或其盐或水合物，以及其制备方法和用于制备的新中间体，含有所述化合物的药物组合物以及所述化合物在治疗中的应用。
• A versatile solid-phase synthesis of 3-aryl-1,2,4-oxadiazolones and analogues
  作者：Julie Charton、Nicolas Cousaert、Christophe Bochu、Nicolas Willand、Benoît Déprez、Rébecca Déprez-Poulain

  DOI：10.1016/j.tetlet.2006.12.050

  日期：2007.2

  We report here the first method to load acidic heterocyclic compounds (1,2,4-oxadiazol-5-one, 1,2,4-oxadiazol-5-thione and 1,2,3,5-oxathiadazol-2-oxide) on a polymer. Using Mitsunobu conditions, these heterocycles were anchored on a 4-hydroxymethyl-3-methoxyphenoxybutyric acid benzhydrylamine (HMPB-BHA) resin. After diversification, compounds can be recovered by a simple treatment in diluted TFA. To

  我们在这里报告了第一种装载酸性杂环化合物的方法（1,2,4-恶二唑-5-酮，1,2,4-恶二唑-5-硫酮和1,2,3,5-恶二唑-2-氧化物）在聚合物上。在Mitsunobu条件下，这些杂环被固定在4-羟甲基-3-甲氧基苯氧基丁酸苯甲基胺（HMPB-BHA）树脂上。多样化后，可以通过在稀释的TFA中进行简单处理来回收化合物。为了说明该方法的实用性，将碘代苯基衍生物固定在同一树脂上。HRMAS-NMR分析揭示了在Mitsunobu条件下这些杂环的反应性。随后使用Sonogashira偶联进行的多样化生产了新的（芳基乙炔基）-苯基-1,2,4-恶二唑-5-酮的小阵列。