trans-cinnamaldehyde thiosemicarbazone | 62337-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-cinnamaldehyde thiosemicarbazone
• 英文别名: 2-((E)-3-phenyl-2-propenylidene)-1-hydrazinecarbothioamide；(E)-cinnamaldehyde thiosemicarbazone；Cinnamaldehyd-thiosemicarbazon；syn-Zimtaldehyd-thiosemicarbazon；dichloride trans-cinnamaldehyde thiosemicarbazone；trans-Zimtaldehyd-thiosemicarbazon；cinnamaldehyde thiosemicarbazone；[[(E)-3-phenylprop-2-enylidene]amino]thiourea
• CAS: 62337-05-7
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: SHUQFXIRXYXNOZ-MCOJTXNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-cinnamaldehyde thiosemicarbazone 在 盐酸 、 三氯化铁 作用下， 生成 5-(2-苯基乙烯基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  Maffii et al., Farmaco, Edizione Scientifica, 1958, vol. 13, p. 187,196

  摘要：

  DOI：
• 作为产物：
  描述：

  反式肉桂醛 、 氨基硫脲 以 乙醇 为溶剂， 反应 8.0h， 以96%的产率得到trans-cinnamaldehyde thiosemicarbazone
  参考文献：
  名称：

  基于肉桂醛硫半碳素类似物的金属配合物的抗菌活性。

  摘要：

  微生物抗生素抗性的发展已成为对全球健康的最大威胁之一，寻找对抗药性致病菌株具有活性的新分子是必须解决的挑战。在许多情况下，医院感染是由细菌引起的，这种细菌的特征是具有多种药物耐药性，并且具有产生生物膜的能力。这些特性导致病原体在医院环境中的持久性。本文报道了一种基于含有肉桂醛天然支架但具有不同logPow值的化合物的三种硫半脲衍生物的合成和表征。然后将这些分子用作配体以制备Cu（II）和Zn（II）离子的络合物。所有这些化合物，配体和络合物，在大肠杆菌和肺炎克雷伯菌的污渍上进行体外筛选，以了解它们的抗菌活性。尽管它们在分子上相似，但它们表现出各种各样的行为。它们中只有两个具有令人感兴趣的抗菌特性，并且也已进行研究以验证其在溶液中的稳定性。具有最低分配系数的化合物是最有前途的。这些物质在肺炎克雷伯菌和大肠杆菌上的最低杀菌浓度是非常有趣的，并证明了使用金属抗生素是对抗抗生素耐药性的一种有前途的

  DOI：

  10.1016/j.jinorgbio.2019.110888

文献信息

• Regioselective N(2)-H-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile
  作者：Anastasiya G. Mal’kina、Valentina V. Nosyreva、Alexander I. Albanov、Andrei V. Afonin、Alexander V. Vashchenko、Svetlana V. Amosova、Boris A. Trofimov

  DOI：10.1080/00397911.2016.1257723

  日期：2017.1.17

  ABSTRACT Regioselective N(2)-H-cyanoethylation of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile proceeds under mild conditions (14% KOH, acetone/H2O, 35 °C, 6–21 h) to afford 1-(2-сyanoethyl)-2-[(E)-aryl(heteroaryl)methylidene]-1-hydrazinecarbothioamides in up to 74% yields. The synthesized thioamides are promising precursors of novel families of functionalized thiosemicarbazones

  摘要 在温和条件（14% KOH、丙酮/H2O、35°C、6-21 小时）下，芳族和杂芳族醛的缩氨基硫脲与丙烯腈的区域选择性 N(2)-H-氰乙基化反应得到 1-(2-氰乙基) -2-[(E)-芳基(杂芳基)亚甲基]-1-肼碳硫酰胺，产率高达 74%。合成的硫代酰胺是功能化缩氨基硫脲新家族的有前途的前体，例如将其氰基水解为相应的酰胺基官能团（产率 46.5-60%）。图形概要
• Synthesis, spectral characterization and DNA interactions of 5-(4-substituted phenyl)-1,3,4-thiadiazol-2-amine scaffolds
  作者：N. Shivakumara、P. Murali Krishna

  DOI：10.1016/j.molstruc.2019.126999

  日期：2020.1

  Five 5-(4-Substituted phenyl)-1, 3, 4-thiadiazole-2-amines have been prepared and structure of the compounds confirmed by spectroscopy studies. On the basis of spectroscopic studies, confirmed the formation of compounds. The DNA binding affinity of the prepared compounds was undertaken by absorption titration method and increasing the amount of CT-DNA observed hyperchromism or hypsochromism. The binding affinity compounds (except 5) are in the order of 4[13.341 x 10(4) M-1]>3 [8.505 x 10(4) M-1]>2 [3.567 x 10(4) M-1]>1[3.525 x 10(4) M-1]. The ethidiumbromide quenching results indicates CT-DNA was quenched by thiadiazoles via a static quenching mechanism. The DNA cleavage studies of the compounds were carried out in the presence and absence of H2O2 using gel electrophoresis experiment. (C) 2019 Elsevier B.V. All rights reserved.
• Synthesis of 1,2,4-triazoles employing isocyanides
  作者：Pakornwit Sarnpitak、Mikhail Krasavin

  DOI：10.1016/j.tet.2013.01.039

  日期：2013.3

  A conceptually new, two-step synthesis of medicinally important 1,2,4-triazoles from isocyanides and thiosemicarbazones was developed. The method is based on the recently discovered TMSCI-promoted reaction of isocyanides that yields rare N-1,N-3-disubstututed formamidrazones. (C) 2013 Elsevier Ltd. All rights reserved.
• In vitro evaluation of the activity of thiosemicarbazone derivatives against mycotoxigenic fungi affecting cereals
  作者：Francesca Degola、Caterina Morcia、Franco Bisceglie、Francesca Mussi、Giorgio Tumino、Roberta Ghizzoni、Giorgio Pelosi、Valeria Terzi、Annamaria Buschini、Francesco Maria Restivo、Tiziana Lodi

  DOI：10.1016/j.ijfoodmicro.2015.02.009

  日期：2015.5

  With a steadily increasing world population, a more efficient system of food production is of paramount importance. One of the major causes of food spoilage is the presence of fungal pathogens and the production and accumulation of mycotoxins. In the present work we report a study on the activity of a series of functionalized thiosemicarbazones (namely cuminaldehyde, trans-cinnamaldehyde, quinoline-2-carboxyaldehyde, 5-fluoroisatin thiosemicarbazone and 5-fluoroisatin N4-methylthiosemicarbazone), as antifungal and anti-mycotoxin agents, against the two major genera of cereal mycotoxigenic fungi, i.e. Fusarium and Aspergillus. These thiosemicarbazones display different patterns of efficacy on fungal growth and on mycotoxin accumulation depending on the fungal species. Some of the molecules display a greater effect on mycotoxin synthesis than on fungal growth. (C) 2015 Elsevier B.V. All rights reserved.
• Chabrier; Cattelain, Bulletin de la Societe Chimique de France, 1950, p. 48,53
  作者：Chabrier、Cattelain

  DOI：——

  日期：——