4-bromobenzaldehyde isonicotinoylhydrazone | 62984-48-9

• 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
• 英文名称: 4-bromobenzaldehyde isonicotinoylhydrazone
• 英文别名: N'-(4-bromobenzylidene)isonicotinohydrazide；isonicotinic acid N2-(4-bromobenzylidene)hydrazide；N-[(4-bromophenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 62984-48-9
• 化学式: C₁₃H₁₀BrN₃O
• mdl: MFCD00450505
• 分子量: 304.146
• InChiKey: WJDGJNGJDIMLRB-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  4-bromobenzaldehyde isonicotinoylhydrazone 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 4.17h， 生成 1-(5-(4-bromophenyl)-3-(pyridin-4-yl)-4,5-dihydro-1,2,4-triazol-1-yl)ethanone
  参考文献：
  名称：

  SYNTHESIS OF SOME 2,3-DIHYDRO-1,3,4-OXADIAZOLES AND 4,5-DIHYDRO-1,2,4-TRIAZOLES AS ANTICANCER AGENTS

  摘要：

  目的：本研究的主要目的是合成和评价新型的2,3-二氢-1,3,4-噁二唑和4,5-二氢-1,2,4-三唑衍生物的细胞毒活性。 方法：通过在回流乙酸酐中环化N'-(取代苯基亚甲基)异烟肼酰肼3a-e，合成了2,3-二氢-1,3,4-噁二唑衍生物4a-h。将2,3-二氢-1,3,4-噁二唑衍生物4a-h转化为相应的4,5-二氢-1,2,4-三唑5a-h，使用氨水。根据物理和光谱数据鉴定了所有合成的化合物。使用Sulforhodamine B（SRB）比色法，评估了标题化合物对人类癌细胞系（MCF-7）的细胞毒活性。 结果：所有合成的化合物在FTIR，1HNMR和质谱分析中显示出特征峰。体外细胞毒活性的结果表明，化合物4c与标准药物多柔比星（IC50 = 8.02 µM）相比，表现出等效的细胞毒活性，其IC50值为8.04 µM。其他化合物与参考标准相比，显示出良好至中等的细胞毒活性。 结论：我们以定量收率合成了一系列标题化合物。大多数衍生物表现出中等至良好的细胞毒活性。

  DOI：

  10.22159/ijpps.2020v12i8.36508
• 作为产物：
  描述：

  异烟酸 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 4-bromobenzaldehyde isonicotinoylhydrazone
  参考文献：
  名称：

  Synthesis and testing of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives for antifungal activity against selected Candida Species

  摘要：

  A series of 21 1,3,4-oxadiazoline derivatives was synthesized by cyclization of N-acylhydrazones with acetic anhydride and evaluated for their in vitro antifungal activity against six Candida strains: Candida albicans (ATCC 90028 and LM V-42), C. krusei (ATCC 6258 and LM 12 C) and C. tropicalis (ATCC 13803 and LM 14). The Candida strains were found to be sensitive to some of the compounds, which inhibited the growth by 50-90%, with minimum inhibitory concentration (MIC) in the range of 64-512 mu g mL(-1). The compounds' structures were fully confirmed and characterized by Fourier transform infrared spectroscopy (FTIR), H-1 and C-13 nuclear magnetic resonance (NMR) and mass spectrometry (MS).

  DOI：

  10.1590/s0103-50532013000100016

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.
• Abou Sekkina, Morsy M.; Abou El-Azm, M. G., Thermochimica Acta, 1984, vol. 79, p. 47 - 54
  作者：Abou Sekkina, Morsy M.、Abou El-Azm, M. G.

  DOI：——

  日期：——
• New isoniazid derivatives with improved pharmaco-toxicological profile: Obtaining, characterization and biological evaluation
  作者：Ionut Dragostin、Oana M. Dragostin、Sangram Keshari Samal、Saumya Dash、Rodica Tatia、Maria Dragan、Luminița Confederat、Cristina M. Ghiciuc、Daniela Diculencu、Cătălina E. Lupușoru、Carmen L. Zamfir

  DOI：10.1016/j.ejps.2019.104974

  日期：2019.9

  Tuberculostatic drugs are the most common drug groups with global hepatotoxicity. Awareness of potentially severe hepatotoxic reactions is vital, as hepatic impairment can be a devastating and often fatal condition. The treatment problems that may arise, within this class of medicines, are mainly of two types: adverse reactions (collateral, toxic or hypersensitive reactions) and the initial or acquired resistance of Mycobacterium tuberculosis to one or more antituberculosis drugs. Prevention of adverse reactions, increase treatment adherence and success rates, providing better control of tuberculosis (TB). In this regard, obtaining new drugs with low toxicity and high tuberculostatic potential is essential. Thus, in this work, we have designed or synthesized new derivatives of isoniazid (INH), such as new Isonicotinoylhydrazone (INH-a, INH-b and INH-c). These derivatives demonstrated good biocompatibility, antimicrobial property similar to that of parent isoniazid and last but not least, a significantly improved Pharmacotoxicological profile compared to that of isoniazid.
• SYNTHESIS OF SOME 2,3-DIHYDRO-1,3,4-OXADIAZOLES AND 4,5-DIHYDRO-1,2,4-TRIAZOLES AS ANTICANCER AGENTS
  作者：TAWFEEK A. YAHYA、JALAL H. ABDULLAH

  DOI：10.22159/ijpps.2020v12i8.36508

  日期：——

  Objective: The main objective of this work was to synthesize and evaluate the novel 2,3-dihydro-1,3,4-oxadiazole and 4,5-dihydro-1,2,4-triazole derivatives for cytotoxic activities. Methods: The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were synthesized by cyclization of N'-(substituted-benzylidene) isonicotinohydrazide 3a-e in refluxing acetic anhydride. The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were converted into the corresponding 4,5-dihydro-1,2,4-triazoles 5a-h using ammonia. All the synthesized compounds were identified, depending on the physical and spectral data. Title compounds were assessed for their cytotoxic activity against human cancer cell line (MCF-7) by using Sulforhodamine B (SRB) colorimetric assay. Results: All the synthesized compounds showed characteristic peaks in FTIR, 1HNMR and Mass spectral analysis. The results of the in vitro cytotoxic activity revealed that the compound 4c exhibited equipotent cytotoxic activity with an IC50 value of 8.04 µM when compared with that of standard drug doxorubicin (IC50= 8.02 µM). The reminder compounds have shown good to moderate cytotoxic activities when compared with that of a reference standard. Conclusion: We synthesized a series of title compounds in quantitative yields. Most derivatives showed moderate to good cytotoxic activity.  

  目的：本研究的主要目的是合成和评价新型的2,3-二氢-1,3,4-噁二唑和4,5-二氢-1,2,4-三唑衍生物的细胞毒活性。 方法：通过在回流乙酸酐中环化N'-(取代苯基亚甲基)异烟肼酰肼3a-e，合成了2,3-二氢-1,3,4-噁二唑衍生物4a-h。将2,3-二氢-1,3,4-噁二唑衍生物4a-h转化为相应的4,5-二氢-1,2,4-三唑5a-h，使用氨水。根据物理和光谱数据鉴定了所有合成的化合物。使用Sulforhodamine B（SRB）比色法，评估了标题化合物对人类癌细胞系（MCF-7）的细胞毒活性。 结果：所有合成的化合物在FTIR，1HNMR和质谱分析中显示出特征峰。体外细胞毒活性的结果表明，化合物4c与标准药物多柔比星（IC50 = 8.02 µM）相比，表现出等效的细胞毒活性，其IC50值为8.04 µM。其他化合物与参考标准相比，显示出良好至中等的细胞毒活性。 结论：我们以定量收率合成了一系列标题化合物。大多数衍生物表现出中等至良好的细胞毒活性。
• Synthesis and testing of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives for antifungal activity against selected Candida Species
  作者：Cledualdo S. de Oliveira、Bruno F. Lira、José M. Barbosa-Filho、Jorge G. F. Lorenzo、Camilla P. de Menezes、Jessyca M. C. G. dos Santos、Edeltrudes de O. Lima、Petrônio F. de Athayde-Filho

  DOI：10.1590/s0103-50532013000100016

  日期：——

  A series of 21 1,3,4-oxadiazoline derivatives was synthesized by cyclization of N-acylhydrazones with acetic anhydride and evaluated for their in vitro antifungal activity against six Candida strains: Candida albicans (ATCC 90028 and LM V-42), C. krusei (ATCC 6258 and LM 12 C) and C. tropicalis (ATCC 13803 and LM 14). The Candida strains were found to be sensitive to some of the compounds, which inhibited the growth by 50-90%, with minimum inhibitory concentration (MIC) in the range of 64-512 mu g mL(-1). The compounds' structures were fully confirmed and characterized by Fourier transform infrared spectroscopy (FTIR), H-1 and C-13 nuclear magnetic resonance (NMR) and mass spectrometry (MS).