(E)-N’-(4'-chlorobenzylidene)isonicotinohydrazide | 1042157-24-3

• 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: (E)-N’-(4'-chlorobenzylidene)isonicotinohydrazide
• 英文别名: N'-(4-chlorobenzylidene)isonicotinohydrazide；N-[(E)-(4-chlorophenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 1042157-24-3
• 化学式: C₁₃H₁₀ClN₃O
• 分子量: 259.695
• InChiKey: AMDRLZATAWMLKJ-CXUHLZMHSA-N

物化性质

• 熔点：
  189-191 °C(Solv: ethanol (64-17-5))
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：

  (E)-N’-(4'-chlorobenzylidene)isonicotinohydrazide 、 阿司匹林 以 乙醇 为溶剂， 反应 0.17h， 生成 (E)-4-(2-(4-chlorobenzylidene)hydrazine-1-carbonyl)pyridin-1-ium 2-acetoxybenzoate
  参考文献：
  名称：

  Synthesis, characterization, in silico studies and in vitro biological evaluation of isoniazid-hydrazone complexes

  摘要：

  Isoniazid-hydrazone complexes (IHCs) were synthesized and thoroughly characterized by FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques. The anti-in fl ammatory and antidiabetic activities were tested for the IHCs using protein denaturation methods and the a-amylase inhibitory method. The molecular modeling studies for IHCs were investigated and their molecular parameters were calculated using Density Functional Theory methods. The IHCs showed lower band gap and higher electrophilicity index values. Further, molecular docking studies were investigated against the a-amylase enzyme to compare the experimental results. The isoniazid hydrazone-salicylic acid complex (3c) showed fi ve hydrogen bonding interactions with amino acid residues of the alpha-amylase enzyme (1HNY). (c) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2020.128297
• 作为产物：
  描述：

  异烟肼 、 4-氯苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以92%的产率得到(E)-N’-(4'-chlorobenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  烟碱/异烟酸肼的黄嘌呤氧化酶抑制活性：从体外，计算机模拟到体内研究的系统方法。

  摘要：

  生活方式和饮食习惯的改变导致全球高尿酸血症的患病率增加。高尿酸血症的作用不再局限于痛风，而在CVD，高血压，代谢综合征和关节炎的进展中起着核心作用。在涉及调节血清尿酸的不同因素中，黄嘌呤氧化酶（XO）是控制血清尿酸水平的最佳药理学靶标，因为它催化了尿酸生产的最终步骤。在当前的研究中，从合成到体外筛选，再到体内研究，对黄嘌呤氧化酶抑制剂进行了系统的研究。通过用取代的芳族醛处理烟碱/异烟碱酰肼来合成苄叉烟碱/异烟碱酰肼（1-54），并通过EI-MS和1H NMR进行表征。还进行了元素分析。首先使用体外光谱XO抑制试验筛选所有合成化合物的黄嘌呤氧化酶抑制活性。与标准药物别嘌呤醇IC50 = 2.00±0.01μM相比，发现其中22种衍生物的IC50值为0.96至330.4μM。对五种活性最高的化合物（8、35、36、39和45）进行了动力学研究，其IC50值在0.96至54.8μM之间，具有抑制

  DOI：

  10.1016/j.bmc.2017.02.044

文献信息

• Thiazolidin-4-one, azetidin-2-one and 1,3,4-oxadiazole derivatives of isonicotinic acid hydrazide: Synthesis and their biological evaluation
  作者：Sadaf Gilani、Suroor Khan、Ozair Alam、Vijender Singh、Alka Arora

  DOI：10.2298/jsc101104092g

  日期：——

  A series of thiazolidin-4-one (2a-h, 3a-h), azetidin-2-one (4a- h) and 1,3,4-oxadiazole (5a-h) derivatives of isoninicotinic acid hydrazide (INH) were synthesized in order to obtain new compounds with potential anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities. The structures of the new compounds were supported by their IR, 1H-NMR and mass spectral data. All compounds were evaluated for their anti-inflammatory activity by the carrageenan-induced rat paw edema test method. Eleven of the new compounds, out of 32, showed very good anti-inflammatory activity in the carrageenan-induced rat paw edema test, with significant analgesic activity in the tail immersion method together with negligible ulcerogenic action. The compounds, which showed less ulcerogenic action, also showed reduced malondialdehyde content (MDA), which is one of the by-products of lipid peroxidation. The study showed that the compounds inhibited the induction of gastric mucosal lesions and it can be suggested from the results that their protective effects may be related to inhibition of lipid peroxidation in the gastric mucosa.

  一系列噻唑烷-4-酮（2a-h，3a-h）、氮杂环丁烷-2-酮（4a-h）和 异烟酸酰肼（INH）的一系列噻唑烷-4-酮（2a-h，3a-h）、氮杂环丁烷-2-酮（4a-h）和 1,3,4-噁二唑（5a-h）衍生物的 合成了异烟酸酰肼（INH）衍生物，以获得具有潜在 新化合物具有潜在的抗炎、镇痛、致溃疡和脂质过氧化活性。 新化合物的结构得到了红外光谱、1H-NMR 和 质谱数据支持了新化合物的结构。所有化合物的抗炎活性都通过角叉菜胶诱导的 抗炎活性。在 32 个新化合物中 在卡拉胶诱导的大鼠爪水肿试验中表现出很好的抗炎活性。 在角叉菜胶诱导的大鼠爪水肿试验中表现出很好的抗炎活性，在尾部浸泡法中表现出显著的镇痛活性，同时还表现出很强的抗菌活性。 在尾部浸泡法中具有显著的镇痛活性，而致溃疡作用则微乎其微。 致溃疡作用较弱的化合物还显示出较低的 丙二醛含量（MDA）。 过氧化物。研究表明，这些化合物抑制了诱导的 研究结果表明，这些化合物抑制了胃黏膜病变的诱导。 保护作用可能与抑制胃黏膜脂质过氧化有关。 胃黏膜的脂质过氧化作用有关。
• Anti-infective compounds
  申请人：Brodin Priscille

  公开号：US20110178077A1

  公开（公告）日：2011-07-21

  The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及小分子化合物及其在治疗细菌感染，特别是结核病方面的用途。
• Polarographic and Cyclic Voltammetric Reduction of<i>p</i>-Chlorobenzaldehyde Isonicotinoylhydrazone
  作者：Papammagari Raveendra Reddy、Sukuru Brahmaji Rao

  DOI：10.1246/bcsj.61.1397

  日期：1988.4

  p-Chlorobenzaldehyde isonicotinoylhydrazone (p-Cl-BAINH) exibits a single wave in acid buffered solutions (pH 2–6) and two waves in alkaline buffered solutions (pH 7–9). However, the compound exhibits three cathodic peaks in acid solution and two cathodic peaks in alkaline solutions. The electrode reactions are attributed to the reductive cleavage of =N–N– linkage and the reduction of the amide formed

  对氯苯甲醛异烟酰腙 (p-Cl-BAINH) 在酸性缓冲溶液 (pH 2-6) 中呈现单波，在碱性缓冲溶液 (pH 7-9) 中呈现两波。然而，该化合物在酸性溶液中表现出三个阴极峰，在碱性溶液中表现出两个阴极峰。电极反应归因于 =N-N- 键的还原断裂和断裂中形成的酰胺的还原。
• Isonicotinohydrazones as inhibitors of alkaline phosphatase and ecto-5′-nucleotidase
  作者：Pervaiz Ali Channar、Syed Jawad Ali Shah、Sidra Hassan、Zaib un Nisa、Joanna Lecka、Jean Sévigny、Jürgen Bajorath、Aamer Saeed、Jamshed Iqbal

  DOI：10.1111/cbdd.12861

  日期：2017.3

  ecto-5'-nucleotidases (h-e5'NT & r-e5'NT) and alkaline phosphatase isozymes including both bovine tissue-nonspecific alkaline phosphatase (b-TNAP) and tissue specific calf intestinal alkaline phosphatase (c-IAP). These enzymes are implicated in vascular calcifications, hypophosphatasia, solid tumors and cancers, such as colon, lung, breast, pancreas and ovary. All tested compounds were active against both enzymes

  合成了一系列异烟肼衍生物，并针对重组人和大鼠ecto-5'-核苷酸酶（h-e5'NT和r-e5'NT）和碱性磷酸酶同工酶（包括牛组织非特异性碱性磷酸酶（b-TNAP））进行了测试和组织特异性小牛肠碱性磷酸酶（c-IAP）。这些酶与血管钙化，磷酸化不足，实体瘤和癌症有关，例如结肠，肺，乳腺，胰腺和卵巢。所有测试的化合物对两种酶均具有活性。h-e5'NT最有效的抑制剂是衍生物（E）-N'-（1-（3-（4-氟苯基）-5-苯基-4,5-二氢-1H-吡唑-1-基）亚乙基）异烟酰胺（3j），而衍生物（E）-N'-（4-羟基-3-甲氧基亚苄基）异烟酰肼（3g）对r-e5'NT表现出显着的抑制活性。此外，衍生物（E）-N'-（4'-氯苄叉）异烟酰肼（3a）是最有效的牛小肠碱性磷酸酶抑制剂，衍生物（E）-N'-（4-羟基-3-甲氧基苄叉）发现异烟肼（3g）是最有效的牛组织非特异性碱性磷酸酶抑制剂。此外，在
• Eco-Friendly and Highly Efficient Synthesis, Including Multigram Synthesis, of Aldehyde Isonicotinoyl Hydrazones Using Sonochemistry
  作者：Ligia Pinto、Marcus de Souza、Emerson Silva、Carlos Kaiser、Solange Wardell、James Wardell

  DOI：10.2174/1570178613666160824123827

  日期：2016.11.29

  Background: The isoniazid has been a key compound in first-line tuberculosis (TB) treatment, usually in combination with other drugs. Following on from the use of isoniazid itself, various derivatives of isoniazid have also been investigated as anti-TB agents and other diseases. This work aims to synthesize, multigram scale, salicylaldehyde isonicotinoyl hydrazone from isoniazid and salicylaldehyde, using ultrasound. Additionally, we have been interested in establishing a general, smaller-scale, ultrasonic driven synthesis of arylaldehyde isoniazid N-acylhydrazones, particularly for use in our biological studies. Methods: A Multiwave Eco-Sonics QR750 ultrasonic generator (20 KHz, 750 W) equipped with a converter/ transducer, and titanium oscillator (horn, diameter = 4 mm) was used for the ultrasonic irradiantion. Compounds were characterized by melting points, infrared spectra, mass spectra (CG/MS), electron microscopy, X-ray powder diffraction, solid-state 13C and solution NMR spectra. Results: This work describes a green chemistry protocol, multigram scale (ca 4 mole) and highly efficient synthesis utilizing ultrasonic irradiation of salicylaldehyde isonicotinoyl hydrazone, a widely used compound in biological studies. With a short reaction time of 30 min, and a facile work up, involving washing with water, the important bioactive product was obtained in a high yield, 98.7%, and in a high purity 99.43%. Also prepared using ultrasonic irradiation with short reaction times, in high yields and high purities, but on smaller scales, were a series arylaldehyde isoniazid N-acylhydrazones, all of which exhibit promising activity against cancer and tuberculosis. Comparisons with the classical procedures indicate advantages in the ultrasonic irradiated methodology. Conclusion: We report the high yielding ultrasonic synthesis of pure salicylaldehyde isonicotinoyl hydrazone on a 4 mole scale. In addition, a series of ten isoniazid N-acylhydrazone derivatives has been obtained using ultrasonic irradiation. The ultrasonic procedures are simple, safe, with short reaction times, and produce high yields.

  背景：异烟肼一直是一线结核病（TB）治疗的关键化合物，通常与其他药物联合使用。继异烟肼本身的使用之后，异烟肼的各种衍生物也被研究用作抗结核药物和其他疾病的药物。这项工作旨在利用超声波从异烟肼和水杨醛中合成多克级的水杨醛异烟酰腙。此外，我们还有兴趣建立一种通用的、较小规模的、超声波驱动的异烟肼 N-酰肼芳基醛合成方法，特别是用于我们的生物研究。 方法：化合物的表征包括熔点、红外光谱、质谱（CG/MS）、电子显微镜、X 射线粉末衍射、固态 13C 和溶液 NMR 光谱。 结果：本研究介绍了利用超声波辐照合成水杨醛异烟酰腙（一种广泛用于生物研究的化合物）的绿色化学方案、多克级（约 4 摩尔）高效合成方法。反应时间短，仅需 30 分钟，操作简便，只需用水冲洗，即可获得重要的生物活性产物，收率高达 98.7%，纯度高达 99.43%。使用超声波辐照法制备的一系列芳基醛类异烟肼 N-酰肼反应时间短、产率高、纯度高，但规模较小。与传统方法相比，超声辐照法更具优势。 结论：我们报告了以 4 摩尔规模高产超声合成纯水杨醛异烟酰腙的方法。此外，我们还利用超声辐照法获得了一系列 10 种异烟肼 N-酰腙衍生物。超声波程序简单、安全、反应时间短、产率高。