1-benzoyl-4-cyclohexylthiosemicarbazide | 26131-20-4

• 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: 1-benzoyl-4-cyclohexylthiosemicarbazide
• 英文别名: 2-benzoyl-N-cyclohexylhydrazinecarbothioamide；1-benzamido-3-cyclohexylthiourea
• CAS: 26131-20-4
• 化学式: C₁₄H₁₉N₃OS
• mdl: MFCD00708380
• 分子量: 277.39
• InChiKey: IMPPXPOJRHFOJR-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzoyl-4-cyclohexylthiosemicarbazide 在 氢氧化钾 、 sodium hydroxide 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 1-[4-[(4-Cyclohexyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]but-2-ynyl]azepane
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 3-(4-tert-amino-2-butynyl)thio and alkyl/alkenylthio-4,5-disubstituted-4H-1,2,4-triazoles

  摘要：

  DOI：

  10.1016/0223-5234(91)90035-l
• 作为产物：
  描述：

  异氰环已烷 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 氘代二甲亚砜 、 乙醇 为溶剂， 反应 5.0h， 生成 1-benzoyl-4-cyclohexylthiosemicarbazide
  参考文献：
  名称：

  通过元素硫促进的肼与异氰酸酯环化反应合成2-氨基-1,3,4-恶二唑

  摘要：

  已开发出一种新的硫促进的酰肼和异腈环化反应以生产1,3,4-恶二唑。该方法操作简单，可与多种底物兼容，可以高效获得各种2-氨基-1,3,4-恶二唑。

  DOI：

  10.1002/cjoc.201700188

文献信息

• Desulfurization Strategy in the Construction of Azoles Possessing Additional Nitrogen, Oxygen or Sulfur using a Copper(I) Catalyst
  作者：Srimanta Guin、Saroj Kumar Rout、Anupal Gogoi、Shyamapada Nandi、Krishna Kanta Ghara、Bhisma K. Patel

  DOI：10.1002/adsc.201200408

  日期：2012.10.8

  A tandem and convergent approach to various N-, O-, or S-containing azoles has been developed by exploiting the thiophilic property of copper(I) iodide used in a catalytic quantity. The present protocol gives access to amino-substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter- or intramolecular attack of suitable

  通过利用催化量使用的碘化亚铜（I）的亲硫特性，已经开发出一种串联和收敛的方法，用于处理各种含N，O或S的唑。本方案通过其各自前体的氧化脱硫，然后通过分子间或分子内攻击合适的亲核试剂，来获得氨基取代的四唑，三唑，恶二唑和噻二唑。对于氨基四唑和三唑，可通过适当调节pK a获得出色的区域选择性与不对称硫脲连接的母体胺的分子量 该方法代表了一种自动催化过程，其中碘化铜（I）被转化为硫化铜（II），硫化铜又转化为活性的氧化铜（II），有效地推进了催化循环。还使用扫描电子显微镜（SEM）和能量色散X射线光谱（EDS）分析研究了铜催化剂的命运，从而深入了解了该催化过程的机理。
• Synthesis, Anti-inflammatory, Antimicrobial Potential and Molecular Docking Studies of 4,5-Disubstituted-1,2,4-Triazole Thioacetate Derivatives
  作者：Muhammad Nouman Arif、Humaira Nadeem、Rehan Zafar Paracha、Arif-ullah Khan、Muhammad Imran、Fawad Ali

  DOI：10.2174/1570180815666180810122226

  日期：2019.6.27

  Background: In the present study synthesis and biological assessment of nine new ethyl [(4,5-disubstituted- 4H-1,2,4-triazol-3-yl)sulfanyl]acetate derivatives 2(a-i) is performed. Methods: The title compounds were characterized by their analytical and spectral data. All the synthesized compounds were screened for their in vivo anti-inflammatory activity using carrageenaninduced rat paw oedema method

  背景：在本研究中，进行了九种新的[（4,5-二取代-4H-1,2,4-三唑-3-基）硫烷基]乙酸乙基酯衍生物2（ai）的合成和生物学评估。 方法：通过分析和光谱数据表征标题化合物。使用角叉菜胶诱导的大鼠爪水肿方法筛选所有合成的化合物的体内抗炎活性和体外抗菌活性。所有化合物均表现出良好的抗炎活性。尤其是化合物2h产生了最大的效果，即与标准双氯芬酸相当，为62.5％。抗菌筛选结果表明，一些新合成的化合物表现出良好的抗菌活性，尤其是对大肠杆菌。 结果：通过对接分析，还研究了所有合成的三唑的硫代乙酸酯衍生物与炎症途径的两个重要靶标酶COX-I和COX-II的相互作用。所有化合物对两种酶均显示出良好的结合亲和力，对COX-1的2e kcal / mol的最大值为-8.1。 结论：对接分析预测我们的化合物与其他非活性NSAIDS一样，通过抑制炎症途径的COX-I和COX-II来非选择性地减轻炎症。
• Hypervalent iodine(V) mediated mild and convenient synthesis of substituted 2-amino-1,3,4-oxadiazoles
  作者：Girish Prabhu、V.V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.05.154

  日期：2012.8

  A simple protocol for the synthesis of 2-amino-1,3,4-oxadiazoles starting from the corresponding acylhydrazides by cyclodesulfurization of intermediate acylthiosemicarbazides mediated by o-iodoxybenzoic acid in good yields has been described. The protocol is mild with wide substrate scope, and thus a range of 2-amino-1,3,4-oxadiazoles have been prepared.

  已经描述了一种简单的方案，该方案通过由邻碘代碘苯甲酸介导的中间体酰基硫代氨基脲在高产率下进行环脱硫，从相应的酰肼开始合成2-氨基-1,3,4-恶二唑。该方案温和，底物范围广，因此已制备了一系列的2-氨基-1,3,4-恶二唑。
• Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-<scp>d</scp>-ribofuranose 2′-Oxidase
  作者：Galina Karabanovich、Jan Dušek、Karin Savková、Oto Pavliš、Ivona Pávková、Jan Korábečný、Tomáš Kučera、Hana Kočová Vlčková、Stanislav Huszár、Zuzana Konyariková、Klára Konečná、Ondřej Jand’ourek、Jiřina Stolaříková、Jana Korduláková、Kateřina Vávrová、Petr Pávek、Věra Klimešová、Alexandr Hrabálek、Katarína Mikušová、Jaroslav Roh

  DOI：10.1021/acs.jmedchem.9b00912

  日期：2019.9.12

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.
• Prabhu, Girish; Madhu, Chilakapathi; Sureshbabu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 865 - 870
  作者：Prabhu, Girish、Madhu, Chilakapathi、Sureshbabu, Vommina V.

  DOI：——

  日期：——