1-(2-fluorobenzoyl)-4-phenylthiosemicarbazide | 443296-88-6

• 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-(2-fluorobenzoyl)-4-phenylthiosemicarbazide
• 英文别名: N-(2-fluorobenzamido)-N'-phenylthiourea；1-[(2-Fluorobenzoyl)amino]-3-phenylthiourea
• CAS: 443296-88-6
• 化学式: C₁₄H₁₂FN₃OS
• 分子量: 289.333
• InChiKey: MMIYDVIPJNCPMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-fluorobenzoyl)-4-phenylthiosemicarbazide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3-(2-fluorophenyl)-1-((4-(4-methylpyrimidin-2-yl)piperazin-1-yl)methyl)-4-phenyl-1H-1,2,4-triazole-5(4H)-thione
  参考文献：
  名称：

  Synthesis and biological activities of some fluorine- and piperazine-containing 1,2,4-triazole thione derivatives

  摘要：

  A series of fluorine- and piperazine-containing 1,2,4-triazole thione derivatives were synthesized by the Mannich reaction of triazole intermediates with various substituted piperazines and formaldehyde in high yields. Structures of title compounds were confirmed by melting points, IR, H-1 NMR, C-13 NMR and elemental analysis. The preliminary bioassays for 17 novel title compounds showed that several compounds have significant fungicidal activity against Cercospora arachidicola, Physalospora piricola and Rhizoctonia cerealis at 50 mu g/mL. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.09.015
• 作为产物：
  描述：

  邻氟苯甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 1-(2-fluorobenzoyl)-4-phenylthiosemicarbazide
  参考文献：
  名称：

  Synthesis and biological activities of some fluorine- and piperazine-containing 1,2,4-triazole thione derivatives

  摘要：

  A series of fluorine- and piperazine-containing 1,2,4-triazole thione derivatives were synthesized by the Mannich reaction of triazole intermediates with various substituted piperazines and formaldehyde in high yields. Structures of title compounds were confirmed by melting points, IR, H-1 NMR, C-13 NMR and elemental analysis. The preliminary bioassays for 17 novel title compounds showed that several compounds have significant fungicidal activity against Cercospora arachidicola, Physalospora piricola and Rhizoctonia cerealis at 50 mu g/mL. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.09.015

文献信息

• Synthesis, characterization and biological activities evaluation of novel sulfanyl derivatives
  作者：Kamuran Saraç、Cahit Orek、Metin Koparir

  DOI：10.1080/10426507.2019.1672692

  日期：2020.3.3

  Abstract A novel series of 1-(3-Methyl-3-mesityl)-cyclobutyl-2-[5-(2-fluorophenyl)-4-(aryl-alkyl)-4H-[1,2,4]triazol-3-yl]sulfanyl}-ethanone compounds were synthesized by a condensation reaction. The new compounds were characterized by elemental analyses, FT-IR and 1H, 13C NMR techniques. The antioxidant and antibacterial properties of the synthesized compounds were also investigated. The in vitro

  摘要 1-(3-甲基-3-甲基)-环丁基-2-[5-(2-氟苯基)-4-(芳基-烷基)-4H-[1,2,4]三唑- 3-基]硫基}-乙酮化合物通过缩合反应合成。通过元素分析、FT-IR 和 1H、13C NMR 技术对新化合物进行了表征。还研究了合成化合物的抗氧化和抗菌性能。测量了新合成化合物的体外抗氧化和抗菌活性，发现它们表现出显着的高抗氧化活性。图形概要
• Antibacterial Activity of Fluorobenzoylthiosemicarbazides and Their Cyclic Analogues with 1,2,4-Triazole Scaffold
  作者：Urszula Kosikowska、Monika Wujec、Nazar Trotsko、Wojciech Płonka、Piotr Paneth、Agata Paneth

  DOI：10.3390/molecules26010170

  日期：——

  The development of drug-resistant bacteria is currently one of the major challenges in medicine. Therefore, the discovery of novel lead structures for the design of antibacterial drugs is urgently needed. In this structure–activity relationship study, a library of ortho-, meta-, and para-fluorobenzoylthiosemicarbazides, and their cyclic analogues with 1,2,4-triazole scaffold, was created and tested for antibacterial activity against Gram-positive bacteria strains. While all tested 1,2,4-triazoles were devoid of potent activity, the antibacterial response of the thiosemicarbazides was highly dependent on substitution pattern at the N4 aryl position. The optimum activity for these compounds was found for trifluoromethyl derivatives such as 15a, 15b, and 16b, which were active against both the reference strains panel, and pathogenic methicillin-sensitive and methicillin-resistant Staphylococcus aureus clinical isolates at minimal inhibitory concentrations (MICs) ranging from 7.82 to 31.25 μg/mL. Based on the binding affinities obtained from docking, the conclusion can be reached that fluorobenzoylthiosemicarbazides can be considered as potential allosteric d-alanyl-d-alanine ligase inhibitors.

  耐药性细菌的产生是目前医学界面临的主要挑战之一。因此，迫切需要发现新的先导结构来设计抗菌药物。在这项结构-活性关系研究中，我们建立了一个由正氟、偏氟和对氟苯甲酰基硫代氨基脲及其 1,2,4-三唑支架环状类似物组成的化合物库，并测试了它们对革兰氏阳性菌株的抗菌活性。虽然所有测试的 1,2,4-三唑类化合物都不具有强效活性，但硫代氨基甲酸盐的抗菌反应与 N4 芳基位置的取代模式有很大关系。15a、15b 和 16b 等三氟甲基衍生物的活性最佳，它们对参考菌株、对甲氧西林敏感的致病性金黄色葡萄球菌和对甲氧西林耐药的金黄色葡萄球菌临床分离株都有活性，最小抑菌浓度 (MIC) 为 7.82 至 31.25 μg/mL。根据对接得到的结合亲和力，可以得出结论，氟苯甲酰基硫代氨基甲酸盐可被视为潜在的异位d-丙氨酰-d-丙氨酸连接酶抑制剂。
• Anion Binding of<i>N</i>-(<i>o</i>-Methoxybenzamido)thioureas: Contribution of the Intramolecular Hydrogen Bond in the<i>N</i>-Benzamide Moiety
  作者：Qian-Qian Jiang、Burenkhangai Darhkijav、Hao Liu、Fang Wang、Zhao Li、Yun-Bao Jiang

  DOI：10.1002/asia.200900519

  日期：2010.3.1

  hydrogen bond identified in 2 X/2 Y. Such an intramolecular hydrogen bond is suggested to be responsible for the enhanced anion binding affinity. In the presence of this intramolecular hydrogen bond, the anion binding constant of 2 X was found to be independent of substituent X at the N‐phenyl ring, as in the case of 1, whereas that of 2 Y showed an amplified dependence on substituent Y at the N′‐phenyl

  ñ - （邻-甲氧基苯甲酰氨基）硫脲（2 X / 2 Y）被发现显示出增强的阴离子与结合常数结合亲和力超过10 7个 摩尔-1 为ACO大小L的订单-和阴离子的红移吸收结合复合体在乙腈（MeCN）相对于N-苯甲酰胺硫脲（1）的乙腈（N-苯甲酰胺部分不具有o- OMe），尽管有o - OMe的供电子特性。的阴离子的吸收2 X / 2 Y复合物显示出的相同的电荷转移性质，该阴离子的1化合物，但它对取代基X的依赖性有趣地受到2 X / 2 Y中鉴定的o -MeO·⋅·HNCO六元环分子内氢键的影响。提示这种分子内氢键负责增强的阴离子结合亲和力。在存在此分子内氢键的情况下，发现2 X的阴离子结合常数与在N-苯环上的取代基X无关，就像在1的情况下一样，而2 Y的阴离子结合常数则显示出对取代基Y的放大依赖性。在N'-苯环上，但程度低于1。据称在2 Za，2 Zd和2 Ze中存在类似的环状分子内氢键，
• Tribromoisocyanuric acid as an alternative oxidant in the synthesis of 2-amino-1,3,4-oxadiazoles from 1-acylthiosemicarbazides
  作者：Jaime Crispim-Neto、Marcio C.S. de Mattos

  DOI：10.1016/j.tetlet.2023.154494

  日期：2023.5

  conversion of 1-acylthiosemicarbazides into 2-amino-1,3,4-oxadiazoles by the reaction with tribromoisocyanuric acid. 1-Acylthiosemicarbazides with diverse substituents such as alkyl, benzyl, and (hetero)aryl were prepared from acylhydrazides and isothiocyanates in up to 97% yield and converted into respective 2-amino-1,3,4-oxadiazoles in 19–93% yield This protocol presents simple reaction conditions,

  已开发出一种简单、有效且环境友好的方法，通过与三溴异氰尿酸反应将 1-酰基氨基硫脲转化为 2-氨基-1,3,4-恶二唑。由酰肼和异硫氰酸酯制备具有不同取代基（如烷基、苄基和（杂）芳基）的 1-酰基氨基硫脲，收率高达 97%，并以 19–93% 的收率转化为相应的 2-氨基-1,3,4-恶二唑该协议提供了简单的反应条件、易于获取的试剂，无需任何特殊设备。
• Synthesis and biological activities of some fluorine- and piperazine-containing 1,2,4-triazole thione derivatives
  作者：Li-Yuan Zhang、Bao-Lei Wang、Yi-Zhou Zhan、Yan Zhang、Xiao Zhang、Zheng-Ming Li

  DOI：10.1016/j.cclet.2015.09.015

  日期：2016.1

  A series of fluorine- and piperazine-containing 1,2,4-triazole thione derivatives were synthesized by the Mannich reaction of triazole intermediates with various substituted piperazines and formaldehyde in high yields. Structures of title compounds were confirmed by melting points, IR, H-1 NMR, C-13 NMR and elemental analysis. The preliminary bioassays for 17 novel title compounds showed that several compounds have significant fungicidal activity against Cercospora arachidicola, Physalospora piricola and Rhizoctonia cerealis at 50 mu g/mL. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.