1-benzylidene-4-phenylthiosemicarbazide | 913329-62-1

• 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-benzylidene-4-phenylthiosemicarbazide
• 英文别名: (E)-2-benzylidene-N-phenylhydrazinecarbothioamide；1-[(E)-benzylideneamino]-3-phenyl-thiourea；1-[(E)-benzylideneamino]-3-phenylthiourea
• CAS: 913329-62-1
• 化学式: C₁₄H₁₃N₃S
• 分子量: 255.343
• InChiKey: AXBWEHNBWRHZBB-RVDMUPIBSA-N

物化性质

• 熔点：
  188 °C
• 沸点：
  390.914±25.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.141±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzylidene-4-phenylthiosemicarbazide 在 重水 、 copper(ll) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  通过氧化杂环合成1,2,4-三唑：在C–S键上形成选择性的C–N键

  摘要：

  通过在由Cu（II）催化的芳基亚芳基硫代半氨基叠氮化物构建4,5-二取代的1,2,4-三唑-3-硫酮的过程中，通过正式的CH官能团化处理，证明了CN比C–S键形成能力更高的倾向。 ）。然而，由邻二取代底物赋予的空间因素倾向于改变反应路径，从而给出以硫代二唑为主要产物或排他性产物。在延长反应时间后，原位生成的硫酮通过脱硫过程转化为4,5-二取代的1,2,4-三唑。两类杂环，即。可以通过简单地调节反应时间，由亚芳基芳基硫代半氨基叠氮化物合成4，5-二取代的1,2,4-三唑-3-硫酮和4,5-二取代的1,2,4-三唑。1,2,4-三唑-3-硫酮的脱硫是通过亲电子铜协助的，从而提供1,2,4-三唑并伴有CuS和多核硫阴离子的形成，这已通过扫描电子显微镜和能量色散X射线光谱法测量得到证实。按照这种策略，已经成功地完成了一锅法合成的抗菌化合物。

  DOI：

  10.1021/acs.joc.5b00956
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 一水合肼 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 5.0h， 生成 1-benzylidene-4-phenylthiosemicarbazide
  参考文献：
  名称：

  Antimicrobial Activity and Structural Study of Disubstituted Thiourea Derivatives

  摘要：

  The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included.

  DOI：

  10.1007/s00706-007-0600-y

文献信息

• Optimization of Antitrypanosomatid Agents: Identification of Nonmutagenic Drug Candidates with in Vivo Activity
  作者：Guzmán Álvarez、Javier Varela、Pablo Márquez、Martín Gabay、Carmen Elena Arias Rivas、Karina Cuchilla、Gustavo A. Echeverría、Oscar E. Piro、Marlus Chorilli、Sandra M. Leal、Patricia Escobar、Elva Serna、Susana Torres、Gloria Yaluff、Ninfa I. Vera de Bilbao、Mercedes González、Hugo Cerecetto

  DOI：10.1021/jm500018m

  日期：2014.5.22

  selectivity and also performed mutagenicity studies. Proof of concept, in vivo studies, was conducted with two of the most promising derivatives (77 and 80). They were identified as candidates because they have (i) very simple and cost-effective syntheses; (ii) activity against different stages and strains of the parasite showing excellent in vivo behavior during the acute phase of Chagas disease; and

  由克鲁斯锥虫寄生虫引起的恰加斯病已在数千年前被描述过。目前，它影响到数以百万计的人，其中大多数在拉丁美洲，并且没有合适的药物来治疗它。为了找到合适的药物来解决这个问题，我们在这里报告了82种新化合物的设计，合成和表征。体外锥虫杀灭行为显示出超过20种具有抗克氏锥虫活性的杰出衍生物。此外，我们研究了对哺乳动物细胞的非特异性毒性，从而确定了它们的选择性，并进行了致突变性研究。使用两种最有希望的衍生物（77和80进行了体内研究的概念验证））。之所以将它们确定为候选者，是因为它们具有（i）非常简单且具有成本效益的综合方法；（ii）在恰加斯病急性期期间，针对不同阶段和种类的寄生虫的活性表现出优异的体内行为；（iii）非特异性毒性或诱变活性。
• (Benzylideneamino)thioureas – Chromogenic Interactions with Anions and N–H Deprotonation
  作者：Marco Bonizzoni、Luigi Fabbrizzi、Angelo Taglietti、Federico Tiengo

  DOI：10.1002/ejoc.200600388

  日期：2006.8

  no)-N′-(R2-substituted-phenyl)thioureas (LH) were designed as anion receptors, and their interactions with anions in MeCN solution were investigated through spectrophotometric and 1H NMR titration experiments. While oxo anions (e.g., CH3COO–, H2PO4–) form genuine H-bond complexes based on complementary N–H···O interactions with LH receptors, the fluoride ion undergoes a two-step interaction, involving

  设计了一系列中性 N-(R1-取代-亚苄基氨基)-N'-(R2-取代-苯基)硫脲 (LH) 作为阴离子受体，并通过分光光度法和 1H NMR 滴定研究了它们与 MeCN 溶液中阴离子的相互作用实验。虽然含氧阴离子（例如 CH3COO–、H2PO4–）基于与 LH 受体互补的 N–H···O 相互作用形成真正的 H 键复合物，但氟离子经历两步相互作用，包括（i）形成[LH…F]– 复合物，以及 (ii) 释放 HF 分子以得到 [HF2]– 和受体的去质子化形式 (L–)。去质子化发生在靠近 R2 取代的苯环的 N-H 片段处，如 1H NMR 光谱所示。[LH…CH3COO]– 氢键复合物形成的log K 值在3.1-3 之间变化。8 范围内，几乎不受 R1 和 R2 取代基的性质影响。所研究的系统可能对分子器件的设计感兴趣，其中不同和远距离取代基的光学特性通过硫脲位点上所选阴离子的相互作用进行调节。
• Chemistry of cyclopropenones: synthesis of new pyrrolo[2,1-b]-1,3,4-oxadiazoles
  作者：Ashraf A. Aly、Alaa A. Hassan、Mohamed A. Ameen、Alan B. Brown

  DOI：10.1016/j.tetlet.2008.04.066

  日期：2008.6

  2,3-Diphenylcyclopropenone (1) reacts with ylidene-N-phenylhydrazine-carbothioamides 2a–e to form the pyrrolo[2,1-b]-1,3,4-oxadiazoles 5a–e.

  2,3-二苯基环丙烯酮（1）与亚烷基-N-苯基肼-碳硫酰胺2a - e反应形成吡咯并[2,1- b ] -1,3,4-恶二唑5a - e。
• Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones
  作者：Qing-Hu Teng、Feng-Lai Lu、Kai Wang、Li-Ya Zhou、Dian-Peng Li

  DOI：10.1021/acs.joc.3c00320

  日期：2023.6.2

  A photocatalytic chemodivergent reaction for the selectivity formation of C–S and C–N bonds in a controlled manner was proposed. The reaction medium, either neutral or acidic, is critical to dictate the formation of 2-amino-1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones from isothiocyanates and hydrazones. This is a practical protocol to achieve the chemoselectivity under mild and metal-free conditions

  提出了一种以受控方式选择性形成 C-S 和 C-N 键的光催化化学发散反应。中性或酸性反应介质对于决定从异硫氰酸酯和腙形成 2-氨基-1,3,4-噻二唑和 1,2,4-三唑-3-硫酮至关重要。这是在温和和无金属条件下实现化学选择性的实用方案。
• Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids
  作者：Thiago M. de Aquino、André P. Liesen、Rosa E.A. da Silva、Vânia T. Lima、Cristiane S. Carvalho、Antônio R. de Faria、Janete M. de Araújo、José G. de Lima、Antonio J. Alves、Edésio J.T. de Melo、Alexandre J.S. Góes

  DOI：10.1016/j.bmc.2007.09.025

  日期：2008.1

  In the present communication, a new series of 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids (2a-p) have been synthesized. Benzaldehyde 4-phenyl-3-thiosemicarbazones substituted (la-p) were also obtained and used as intermediate to give the title compounds. All synthesized compounds were characterized by IR, H-1 and (13) C NMR. The in vitro anti-Toxoplasma gondii activity of la-p and 2a-p was evaluated. The 4-thiazolidinones (2a-p) were screened for their ill vitro antimicrobial activity. For anti-Toxoplasma gondii activity, in general, all compounds promoted decreases in the percentage of infected cells leading to parasite elimination. These effects on intracellular parasites also caused a decrease in the mean number of tachyzoites. In addition, most of the 4-thiazolidinones showed more effective toxicity against intracellular parasites, with IC50 values ranging from 0.05 to 1 mM. According to results of antimicrobial activity, compounds 2f, 21, and 2p showed best activity against Mycobacterium luteus, 2c was more active against Mycobacterium tuberculosis, and 2g, 21, and 2n showed same activity as nistatin (standard drug) against Candida sp. (4249). (c) 2007 Elsevier Ltd. All rights reserved.