methyl 2-pyridyl ketone thiocarbonohydrazone | 96699-87-5

• 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: methyl 2-pyridyl ketone thiocarbonohydrazone
• 英文别名: 2-acetylpyridine thiocarbonohydrazone；3-Amino-1-{[1-(pyridin-2-yl)ethylidene]amino}thiourea；1-amino-3-(1-pyridin-2-ylethylideneamino)thiourea
• CAS: 96699-87-5
• 化学式: C₈H₁₁N₅S
• 分子量: 209.275
• InChiKey: XAHYPRWKUUNOHD-UHFFFAOYSA-N

物化性质

• 沸点：
  366.8±34.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-pyridyl ketone thiocarbonohydrazone 在 叔丁基过氧化氢 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 2-acetylpyridine <5-(2-chloroanilino)-1,3,4-thiadiazol-2-yl>hydrazone
  参考文献：
  名称：

  2-Acetylpyridine thiocarbonohydrazones. Potent inactivators of herpes simplex virus ribonucleotide reductase

  摘要：

  A series of 2-acetylpyridine thiocarbonohydrazones was synthesized for evaluation as potential antiherpetic agents. The compounds were prepared by the condensation of 2-acetylpyridine with thiocarbonohydrazide followed by treatment with isocyanates or isothiocyanates. Many were found that were potent inactivators of ribonucleotide reductase encoded by HSV-1 and weaker inactivators of human enzyme. Several thiocarbonohydrazones (e.g. 38 and 39) inactivated HSV-1 ribonucleotide reductase at rate constants as much as seven times that of lead compound 2. In general, those substituted with weak electron-attracting groups offered the best combination of potency and apparent selective activity against the HSV-1 enzyme. Seven new thiocarbonohydrazones (21, 25, 31, 36, 38, 39, and 40) were apparently greater than 50-fold more selective than 2 against HSV-1 ribonucleotide reductase versus human enzyme. The results indicated new compounds worthy of further study as potentiators of acyclovir in combination topical treatment of herpes virus infections.

  DOI：

  10.1021/jm00090a022
• 作为产物：
  描述：

  2-乙酰基吡啶 、 硫代卡巴肼 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到methyl 2-pyridyl ketone thiocarbonohydrazone
  参考文献：
  名称：

  甲基2-吡啶基酮碳和硫代碳hydr在铜（II）和锌（II）配合物中的螯合行为

  摘要：

  合成了双（甲基2-吡啶基酮）碳-（H 2 L 1）和硫代碳-（H 2 L 2），通过分光光度法研究获得了质子化常数，并通过X射线衍射法确定了其晶体结构。已经研究了它们对铜，氯化锌和乙酸盐的络合行为。结果表明，它们能够与所用的铜盐和乙酸锌形成双金属络合物。这是通过对[Cu 2（HL 1）Cl 3（OH 2）]·1.5H 2 O进行的X射线分析证实的。

  DOI：

  10.1039/dt9960002699

文献信息

• In vitro activity of novel cinnamic acids hydrazides against clinically important pathogens
  作者：Mohamed H. Assaleh、Sanja Jeremić、Ilija Cvijetić、Aleksandar Marinković、Nevena Prlainović

  DOI：10.1016/j.molstruc.2022.133016

  日期：2022.8

  worldwide, whereby derivatives of natural products are becoming more attractive. In the present paper, the microbiological assessment of a series of 12 cinnamide hydrazides, four of them completely novel, against clinically relevant pathogens has discovered several derivatives with promising in vitro activities against Acinetobacter baumannii, one of the most dreaded opportunistic pathogens in hospitals

  抗菌素耐药性（AMR）已成为治疗医院感染时最受关注和极具挑战性的问题。开发新的强效化合物的紧迫性在全球范围内持续增加，因此天然产物的衍生物变得越来越有吸引力。在本文中，对一系列 12 种肉桂酰胺酰肼（其中四种是全新的）针对临床相关病原体的微生物学评估发现了几种对鲍曼不动杆菌具有良好体外活性的衍生物，医院中最可怕的机会性病原体之一。这些化合物是通过将三种不同的天然酸（肉桂酸、4-氯或 4-甲氧基）中的一种与四种单硫代甲腙（MTCH）（一类重要的合成有机分子）结合而合成的。它们的结构通过元素微量分析以及 ATR-FTIR、1 H 和13 C NMR 光谱得到证实，并添加了新化合物的 2D NMR 光谱。肉桂酸和吡啶衍生物的杂化物是特别活跃的化合物，对氯肉桂酸和乙酰基吡啶衍生物的最低 MIC 50值为 10.4 µM 。一个与比对无关的 3D QSAR 模型确定了药效团热点，并提出了一些可能提高
• J. Med. Chem. 1992, 35, 2306-2314
  作者：

  DOI：——

  日期：——
• Chelating behaviour of methyl 2-pyridyl ketone carbono- and thiocarbonohydrazones in copper(II) and zinc(II) complexes
  作者：Alessia Bacchi、A. Bonini、Mauro Carcelli、Fabrizio Ferraro、Enrico Leporati、Corrado Pelizzi、Giancarlo Pelizzi

  DOI：10.1039/dt9960002699

  日期：——

  The compounds bis(methyl 2-pyridyl ketone) carbono-(H2L1) and thiocarbono-hydrazone (H2L2) have been synthesized, their protonation constants obtained through spectrophotometric studies and their crystal structures determined by X-ray diffractometry. Their complexation behaviour has been studied towards copper and zinc chloride and acetate. The results indicate that they are able to form bimetallic

  合成了双（甲基2-吡啶基酮）碳-（H 2 L 1）和硫代碳-（H 2 L 2），通过分光光度法研究获得了质子化常数，并通过X射线衍射法确定了其晶体结构。已经研究了它们对铜，氯化锌和乙酸盐的络合行为。结果表明，它们能够与所用的铜盐和乙酸锌形成双金属络合物。这是通过对[Cu 2（HL 1）Cl 3（OH 2）]·1.5H 2 O进行的X射线分析证实的。
• 2-Acetylpyridine thiocarbonohydrazones. Potent inactivators of herpes simplex virus ribonucleotide reductase
  作者：Todd A. Blumenkopf、Joan A. Harrington、Cecilia S. Koble、Donald D. Bankston、Robert W. Morrison、Eric C. Bigham、Virgil L. Styles、Thomas Spector

  DOI：10.1021/jm00090a022

  日期：1992.6

  A series of 2-acetylpyridine thiocarbonohydrazones was synthesized for evaluation as potential antiherpetic agents. The compounds were prepared by the condensation of 2-acetylpyridine with thiocarbonohydrazide followed by treatment with isocyanates or isothiocyanates. Many were found that were potent inactivators of ribonucleotide reductase encoded by HSV-1 and weaker inactivators of human enzyme. Several thiocarbonohydrazones (e.g. 38 and 39) inactivated HSV-1 ribonucleotide reductase at rate constants as much as seven times that of lead compound 2. In general, those substituted with weak electron-attracting groups offered the best combination of potency and apparent selective activity against the HSV-1 enzyme. Seven new thiocarbonohydrazones (21, 25, 31, 36, 38, 39, and 40) were apparently greater than 50-fold more selective than 2 against HSV-1 ribonucleotide reductase versus human enzyme. The results indicated new compounds worthy of further study as potentiators of acyclovir in combination topical treatment of herpes virus infections.