isonicotinic acid N2-(β-phenylcinnamylidene)hydrazide | 433719-26-7

• 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: isonicotinic acid N2-(β-phenylcinnamylidene)hydrazide
• 英文别名: N-(3,3-diphenylprop-2-enylideneamino)pyridine-4-carboxamide
• CAS: 433719-26-7
• 化学式: C₂₁H₁₇N₃O
• 分子量: 327.385
• InChiKey: UDGMUISAVHFNFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异烟肼 、 β-苯基肉桂醛 以 甲醇 、 水 为溶剂， 生成 isonicotinic acid N2-(β-phenylcinnamylidene)hydrazide
  参考文献：
  名称：

  Reagent Precoated Targets for Rapid In-Tissue Derivatization of the Anti-Tuberculosis Drug Isoniazid Followed by MALDI Imaging Mass Spectrometry

  摘要：

  异烟肼（INH）是治疗肺结核的一线药物的重要组成部分，具有良好的血清药代动力学特性，但其穿透结核病变的能力尚不清楚。然而，内源性背景干扰阻碍了我们直接分析组织中的INH。化学衍生化已成功用于通过基质辅助激光解吸电离（MALDI）成像质谱法（IMS）直接从组织样本中测量异烟肼。在组织切片装载之前，MALDI靶点预先处理了反肉桂醛（CA）。组织中存在的异烟肼被有效地衍生化，并通过MS/MS测量INH-CA产物。MALDI靶点的预涂层允许组织直接解冻装载和衍生化，从而简化了制备过程。一系列来自感染结核病/接受INH治疗的动物的组织进行了时间过程系列检测，MALDI MS/MS的响应与通过高效液相色谱（HPLC）-MS/MS确定的组织中INH含量有很好的相关性。

  DOI：

  10.1007/s13361-011-0150-8

文献信息

• Preparation and antitubercular activities in vitro and in vivo of novel Schiff bases of isoniazid
  作者：Michael J. Hearn、Michael H. Cynamon、Michaeline F. Chen、Rebecca Coppins、Jessica Davis、Helen Joo-On Kang、Abigail Noble、Becky Tu-Sekine、Marianne S. Terrot、Daniella Trombino

  DOI：10.1016/j.ejmech.2009.05.009

  日期：2009.10

  Structural modification of the frontline antitubercular isonicotinic acid hydrazide (INH) provides lipophilic adaptations (3-46) of the drug in which the hydrazine moiety of the parent compound has been chemically blocked from the deactivating process of N-2-acetylation by N-arylaminoacetyl transferases. As a class, these compounds show high levels of activity against Mycobacterium tuberculosis in vitro and in tuberculosis-infected macrophages. They provide strong protection in tuberculosis-infected mice and have low toxicity. With some representatives of this class achieving early peak plasma concentrations approximately three orders of magnitude above minimum inhibitory concentration, they may serve as tools for improving our understanding of INH-based treatment modalities, particularly for those patients chronically underdosed in conventional INH therapy. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Reagent Precoated Targets for Rapid In-Tissue Derivatization of the Anti-Tuberculosis Drug Isoniazid Followed by MALDI Imaging Mass Spectrometry
  作者：M. Lisa Manier、Michelle L. Reyzer、Anne Goh、Veronique Dartois、Laura E. Via、Clifton E. Barry、Richard M. Caprioli

  DOI：10.1007/s13361-011-0150-8

  日期：2011.8.1

  Isoniazid (INH) is an important component of front-line anti-tuberculosis therapy with good serum pharmacokinetics but unknown ability to penetrate tuberculous lesions. However, endogenous background interferences hinder our ability to directly analyze INH in tissues. Chemical derivatization has been successfully used to measure isoniazid directly from tissue samples using matrix-assisted laser desorption/ionization (MALDI) imaging mass spectrometry (IMS). MALDI targets were pretreated with trans-cinnamaldehyde (CA) prior to mounting tissue slices. Isoniazid present in the tissues was efficiently derivatized and the INH-CA product measured by MS/MS. Precoating of MALDI targets allows the tissues to be directly thaw-mounted and derivatized, thus simplifying the preparation. A time-course series of tissues from tuberculosis infected/INH dosed animals were assayed and the MALDI MS/MS response correlates well with the amount of INH determined to be in the tissues by high-performance liquid chromatography (HPLC)-MS/MS.

  异烟肼（INH）是治疗肺结核的一线药物的重要组成部分，具有良好的血清药代动力学特性，但其穿透结核病变的能力尚不清楚。然而，内源性背景干扰阻碍了我们直接分析组织中的INH。化学衍生化已成功用于通过基质辅助激光解吸电离（MALDI）成像质谱法（IMS）直接从组织样本中测量异烟肼。在组织切片装载之前，MALDI靶点预先处理了反肉桂醛（CA）。组织中存在的异烟肼被有效地衍生化，并通过MS/MS测量INH-CA产物。MALDI靶点的预涂层允许组织直接解冻装载和衍生化，从而简化了制备过程。一系列来自感染结核病/接受INH治疗的动物的组织进行了时间过程系列检测，MALDI MS/MS的响应与通过高效液相色谱（HPLC）-MS/MS确定的组织中INH含量有很好的相关性。