(E)-N’-(2',4'-dihydroxybenzylidene)isonicotinohydrazide | 3477-69-8

• 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’-(2',4'-dihydroxybenzylidene)isonicotinohydrazide
• 英文别名: isonicotinic acid-(2,4-dihydroxy-benzylidenehydrazide)；Isonicotinsaeure-(2,4-dihydroxy-benzylidenhydrazid)；N'-(2,4-dihydroxybenzylidene)isonicotinohydrazide；N-[(E)-(2,4-dihydroxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 3477-69-8
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: CKBWTRSIUARPEC-OVCLIPMQSA-N

物化性质

• 溶解度：
  3.6 [ug/mL]

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

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (E)-N’-(2',4'-dihydroxybenzylidene)isonicotinohydrazide 、 7beta-[(Z)-2-(2-氨基噻唑-4-基)-2-(1-羧基-1-甲基乙氧基亚氨基)乙酰氨基]-3-乙酰氧基甲基-3-头孢烯-4-羧酸 在 N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 碘代三甲硅烷 、 四氢呋喃 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 以1%的产率得到
  参考文献：
  名称：

  Antimicrobial effects of novel siderophores linked to β-lactam antibiotics

  摘要：

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00261-8
• 作为产物：
  描述：

  异烟肼 、 2,4-二羟基苯甲醛 反应 1.0h， 以99%的产率得到(E)-N’-(2',4'-dihydroxybenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  合成腙、喹唑啉和希夫碱的有效方法：使用化学计量学方法监测反应

  摘要：

  通过结合合适的醛（2,3- 或 2,4-）可合成腙（ 1a–4a和1b–4b ）、喹唑啉（ 3c·MeOH和3d·MeOH ）和腙-席夫碱（ 4c和4d ）二羟基苯甲醛）与四种酰肼（异烟碱、烟碱和2-或4-氨基苯甲酸酰肼）。描述了一系列制备方法：基于溶液的合成、机械合成和固态熔融反应。对于喹唑啉来说，机械化学方法通常是更好的选择，而对于（异）烟碱基腙的衍生物，固态熔融反应则更有效。结晶胺官能化腙4a和4b在与 3- 或 4-吡啶甲醛蒸气反应中进行合成后修饰，形成腙-席夫碱4a-3py 、 4b-3py 、 4a-4py和4b-4py 。机械化学和蒸汽介导反应之后分别采用异位粉末 X 射线衍射和 IR-ATR 方法。使用主成分分析对这些数据进行化学计量分析，可以深入了解反应曲线和反应时间。由醛和肼获得的吖嗪（ 5a和5b ）会随着温度变化而可逆地改变颜色。所有产品的结构均通过光谱和X射线衍射

  DOI：

  10.1039/d0ra06845d

文献信息

• 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。
• Xanthine oxidase inhibitory activity of nicotino/isonicotinohydrazides: A systematic approach from in vitro , in silico to in vivo studies
  作者：Humaira Zafar、Muhammad Hayat、Sumayya Saied、Momin Khan、Uzma Salar、Rizwana Malik、M. Iqbal Choudhary、Khalid Mohammed Khan

  DOI：10.1016/j.bmc.2017.02.044

  日期：2017.4

  involved in regulation of serum uric acid, xanthine oxidase (XO) is the best pharmacological target to control the levels of serum uric acid as it catalyzes the final steps in uric acid production. In the current study, a systemic search for the inhibitors of xanthine oxidase, starting from synthesis to in vitro screening and leading to in vivo studies is presented. Benzylidene nicotino/isonicotinohydrazides

  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
• Sah; Peoples, Journal of the American Pharmaceutical Association (1912), 1954, vol. 43, p. 513,514
  作者：Sah、Peoples

  DOI：——

  日期：——
• Design, synthesis and in vitro antimalarial activity of an acylhydrazone library
  作者：Patricia Melnyk、Virginie Leroux、Christian Sergheraert、Philippe Grellier

  DOI：10.1016/j.bmcl.2005.09.058

  日期：2006.1

  A library of acylhydrazone iron chelators was synthesized and tested for its ability to inhibit the growth of a chloroquine-resistant strain of Plasmodium falciparum. Some of these new compounds are significantly more active than desferrioxamine DFO, the iron chelator in widespread clinical use and also than the most effective chelators. (c) 2005 Elsevier Ltd. All rights reserved.
• Compounds for Targeting Cancer Stem Cells
  申请人：The General Hospital Corporation

  公开号：US20210238140A1

  公开（公告）日：2021-08-05

  This invention relates to antagonists of G3BP2, G3BP1, and ZEB1. Pharmaceutical compositions comprising G3BP2 inhibitors, methods of inhibiting G3BP2, G3BP1, and ZEB1, methods of treating cancer and inflammation, and methods of identifying an inhibitor of cancer stems cells are also provided.