3,4-dihydroxybenzaldehyde isonicotinoylhydrazone | 13838-18-1

• 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: 3,4-dihydroxybenzaldehyde isonicotinoylhydrazone
• 英文别名: 3,4-DHBINH；3,4-Dihydroxybenzaldehyde isonicotinoyl hydrazone；N-[(3,4-dihydroxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 13838-18-1
• 化学式: C₁₃H₁₁N₃O₃
• mdl: MFCD00432605
• 分子量: 257.249
• InChiKey: FDFDWHTXHDGTDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 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：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异烟肼 、 3,4-二羟基苯甲醛 以 乙醇 、 水 为溶剂， 生成 3,4-dihydroxybenzaldehyde isonicotinoylhydrazone
  参考文献：
  名称：

  Spectral Characterization and Antibacterial Activities of Benzyloxybenzaldehydethiosemicarbazone, 3,4-Dihydroxybenzaldehydeisonicotinoylhydrazone and their Transitional Metal Complexes

  摘要：

  本研究合成并对苄氧基苯甲醛硫脲半胱氨酸酮（BBTSC）进行了光谱特性研究，同时研究了配体BBTSC、3,4-二羟基苯甲醛异尼卡酰肼（3,4-DHBINH）及其过渡金属配合物的抗菌活性。采用Job法、摩尔比法和Asmus法评估了金属配合物的组成。对BBTSC、3,4-DHBINH及其配合物（Cu（II）-BBTSC、Pd（II）-BBTSC、Cr（VI）-3,4-DHBINH、Ti（IV）-3,4-DHBINH和Pd（II）-3,4-DHBINH）在两种革兰氏阳性菌和两种革兰氏阴性菌中的抗菌活性进行了研究。抗菌活性通过琼脂杯孔法和Luria Bertoni平板测定。

  DOI：

  10.1155/2011/579892

文献信息

• Antimicrobial Activities of Synthetic Arylidine Nicotinic and Isonicotinic Hydrazones
  作者：Muhammad Hayat、Khalid Mohammed Khan、Sumayya Saeed、Uzma Salar、Momin Khan、Taimoor Baig、Aqeel Ahmad、Shahnaz Parveen、Muhammad Taha

  DOI：10.2174/1570180814666170914120337

  日期：2018.8.27

  showed significant to moderate antimicrobial activities against Gram positive and Gram negative bacterial cultures. Few compounds also showed antifungal activity against fungal cultures. Minimum Inhibitory Concentration (MIC) was calculated for the most active compounds 1, 7, 11, 19, 34, 46, 50, 51, and 55 against gram positive and gram negative cultures. Conclusion: Newly identified compounds may serve

  背景：尽管可以使用多种抗菌剂，但病原菌的再次出现仍然是严重的医学问题。鉴定新的，安全的和选择性的抗菌剂是药物化学研究的主要兴趣。 方法：研究了合成的亚芳基烟碱和异烟碱（1-63）库的抗菌活性。 结果：许多衍生物显示出对革兰氏阳性和革兰氏阴性细菌培养物具有显着至中等的抗菌活性。很少有化合物也显示出对真菌培养物的抗真菌活性。计算了对革兰氏阳性和革兰氏阴性培养物活性最高的化合物1、7、11、19、34、46、50、51和55的最低抑菌浓度（MIC）。 结论：新鉴定的化合物可作为未来研究的先导，以获得更强大的抗菌剂。
• Solvent-free mechanochemical route for green synthesis of pharmaceutically attractive phenol-hydrazones
  作者：P. F. M. Oliveira、M. Baron、A. Chamayou、C. André-Barrès、B. Guidetti、M. Baltas

  DOI：10.1039/c4ra10489g

  日期：——

  from various substituted organic hydrazines and phenol aldehydes. The degree of conversion was increased by high electronic density on the amino group of the hydrazine reactant, as well as low steric hindrance around both reactive sites. In this particular case, the flexibility of the chain bearing the amino reactive site of hydrazine was highlighted as a factor influencing the reaction rate. The results

  在振动球磨机中成功地由各种取代的有机肼和酚醛合成了一系列潜在的治疗剂azo。肼反应物氨基上的高电子密度以及两个反应位点附近的低位阻均提高了转化度。在这种特定情况下，带有肼的氨基反应位点的链的柔韧性被强调为影响反应速率的因素。结果表明，在不存在副产物的情况下，可以以超过99％的转化率获得。这高度适合于需要高纯度的活性药物成分的合成。
• Screening a small hydrazide-hydrazone combinatorial library for targeting the STAT3 in monocyte-macrophages with insulated reporter transposons
  作者：Valeri V. Mossine、Steven P. Kelley、James K. Waters、Thomas P. Mawhinney

  DOI：10.1007/s00044-023-03028-8

  日期：2023.4

  The Signal Transducer and Activator of Transcription 3 (STAT3) pharmacological targeting is regarded as a prospective approach to treat cancer, autoimmune disorders, or inflammatory diseases. We have developed a series of reporters of the STAT3, NF-κB, Nrf2, metal-responsive transcription factor-1 (MTF-1), and hypoxia-inducible factor 1α (HIF-1α) transcriptional activation in human monocyte-macrophage line THP-1. The reporter lines were employed to test a set of hydrazide-hydrazones as potential STAT3 inhibitors. A hydrazide-hydrazone library composed of 70 binary combinations of 7 carbonyl and 10 hydrazide components, including a STAT3 inhibitor clinical drug nifuroxazide, has been assembled and screened by the reporters. For the library as a whole, significant correlations between responses of the STAT3 and NF-κB or the STAT3 and HIF-1α reporters in THP-1 monocytes were found. For selected inhibitory combinations, respective hydrazide-hydrazones have been prepared and tested individually. The most potent 2-acetylpyridine 4-chlorobenzoylhydrazone exhibited the STAT3 inhibitory potential significantly exceeding that of nifuroxazide (ED₅₀ 2 vs 50 μM respectively) in THP-1 cells. We conclude that insulated reporter transposons could be a useful tool for drug discovery applications.

  Graphical Abstract

  摘要 信号转导和转录激活因子3（STAT3）药物靶向被认为是治疗癌症、自身免疫性疾病或炎症性疾病的一种前瞻性方法。我们开发了一系列STAT3、NF-κB、Nrf2、金属反应性转录因子-1（MTF-1）和缺氧诱导因子1α（HIF-1α）在人单核-巨噬细胞系THP-1中转录激活的报告基因。这些报告基因被用来测试一组作为潜在 STAT3 抑制剂的酰肼。由 7 个羰基成分和 10 个酰肼成分的 70 个二元组合组成的酰肼-酰腙库，包括 STAT3 抑制剂临床药物硝呋沙齐，已经组装完成并通过报告基因筛选。就整个库而言，在 THP-1 单核细胞中发现 STAT3 和 NF-κB 或 STAT3 和 HIF-1α 报告物的反应之间存在明显的相关性。针对选定的抑制组合，制备了相应的酰肼，并进行了单独测试。在 THP-1 细胞中，最有效的 2-乙酰基吡啶-4-氯苯甲酰腙对 STAT3 的抑制潜力明显超过硝呋沙齐（ED50 分别为 2 和 50 μM）。我们的结论是，绝缘报告转座子可能是药物发现应用的有用工具。 图表摘要
• Determination of Traces of Pd(II) in Spiked Samples by Using 3,4-Dihydroxybenzaldehydeisonicotinol-hydrazone as a Chelating Agent with UV Visible Spectrophotometer
  作者：S. Lakshmi Narayana、C. Ramachandraiah、A. Varada Reddy、Dongyeun Lee、Jaesool Shim

  DOI：10.1155/2011/612302

  日期：——

  A simple, rapid, sensitive and inexpensive method has been developed for the determination of trace amounts of palladium(II) using 3,4-dihydroxybenzaldehydeisonicotinoylhydrazone (3,4-DHBINH). The metal ion gives a yellow colored complex with 3,4-DHBINH in acetate buffer of pH 3.0 with 1:1 (metal: ligand) composition. The complex shows maximum absorption at 380 nm. Beer’s law is obeyed in the range 0.5-20.0 ppm of Pd(II). The molar absorptivity, Sandell’s sensitivity and detection limit were found to be 0.53×10⁴L mol^-1cm^-1, 0.02 μg cm^-2and 0.0948 μg mL^-1, respectively. The correlation coefficient and regression coefficient of the Pd(II)-3,4-DHBINH complex were 1.08 and 0.04 respectively. Major cations and anions did not show any interference. Anti-microbial activity of the Pd(II)-3,4-DHBINH has been studied. The developed method has been successfully applied to the analysis of Pd(II) in spiked samples. Comparing the results with those obtained using an atomic absorption spectrophotometer tested the validity of the method

  利用 3,4-二羟基苯甲醛异烟酰腙（3,4-DHBINH）建立了一种简单、快速、灵敏和廉价的痕量钯（II）测定方法。在 pH 值为 3.0 的醋酸盐缓冲液中，金属离子与 3,4-DHBINH 生成了一种黄色的络合物，络合物的成分为 1:1（金属：配体）。络合物在 380 纳米波长处显示出最大吸收。钯（II）在 0.5-20.0 ppm 的范围内遵循比尔定律。摩尔吸收率、桑德尔灵敏度和检测限分别为 0.53×104L moL-1 cm-1、0.02 μg cm-2 和 0.0948 μg mL-1。Pd(II)-3,4-DHBINH 复合物的相关系数和回归系数分别为 1.08 和 0.04。主要的阳离子和阴离子没有显示出任何干扰。研究了 Pd(II)-3,4-DHBINH 的抗微生物活性。所开发的方法已成功应用于分析加标样品中的钯(II)。将结果与使用原子吸收分光光度计获得的结果进行比较，检验了该方法的有效性。