4-[(carbamothioylhydrazono) methyl] phenyl 4-methylbenzenesulfonate

• 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: 4-[(carbamothioylhydrazono) methyl] phenyl 4-methylbenzenesulfonate
• 英文别名: [4-[(Carbamothioylhydrazinylidene)methyl]phenyl] 4-methylbenzenesulfonate
• 化学式: C₁₅H₁₅N₃O₃S₂
• 分子量: 349.434
• InChiKey: LDVMAZRRSFJVEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(carbamothioylhydrazono) methyl] phenyl 4-methylbenzenesulfonate 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 [Co(4-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)hydrazono]methylphenyl 4-methylbenzenesulfonate)₂(Cl)₂]
  参考文献：
  名称：

  Synthesis, physicochemical properties, biological, molecular docking and DFT investigation of Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes of the 4-[(5-oxo-4,5-dihydro-1,3-thiazol-2-yl)hydrazono]methyl}phenyl 4-methylbenzenesulfonate Schiff-base ligand

  摘要：

  4-methylbenzenesulfonate (L), and its Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes were synthesized and characterized. Elemental analysis, NMR spectroscopy, mass spectra, FT-IR analysis, molar conductivity, magnetic susceptibility tests and electronic spectra (UV-vis.) were all used to describe the ligand and its metal complexes. The complexes of Ni(II) and Zn(II) were found to have a tetrahedral

  DOI：

  10.1016/j.poly.2022.116219
• 作为产物：
  描述：

  对甲苯磺酰氯 在 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 4-[(carbamothioylhydrazono) methyl] phenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  含噻唑烷-4-一环的新型羧酸盐和磺酸盐的合成及对某些代谢酶的抑制性能评价

  摘要：

  以优异的收率（94-97%）合成了一系列噻唑烷-4-酮衍生物（3a-o），并通过傅里叶变换红外（FTIR）、核磁共振（1 H NMR—）对化合物的结构进行了表征。 13 C NMR）和高分辨率质谱（HRMS）。新型化合物针对一些代谢酶进行了测试，包括乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶 (BChE) 和人碳酸酐酶 I-II (hCA I-II)。与标准乙酰唑酰胺 K i相比，所有合成类似物均具有有效的抑制强度，对 hCA-I 的 K i值在 161.28 ± 16.91–943.13 ± 57.23 nM 范围内，对 hCA-II 的 K i 值在 151.77 ± 21.42–879.89 ± 57.70 nM 范围内。 = 847.18 ± 75.41nM（对于 hCA-I），K i  = 776.12 ± 70.62nM（对于 hCA-II）。大多数化合物对AChE和BChE酶表

  DOI：

  10.1007/s13738-023-02861-3

文献信息

• Synthesis, characterization, biological activity and molecular docking studies of novel schiff bases derived from thiosemicarbazide: Biochemical and computational approach
  作者：Feyzi Sinan Tokalı、Parham Taslimi、Hande Usanmaz、Muhammet Karaman、Kıvılcım Şendil

  DOI：10.1016/j.molstruc.2020.129666

  日期：2021.5

  mass spectrometry (HRMS) spectroscopic methods. AChE was inhibited by these novel Schiff bases (2a-h) in low nanomolar levels, the Ki of which differed between 592.66 ± 57.04 and 810.78 ± 84.06 nM. Against BChE, the novel compounds demonstrated Kis varying from 358.31 ± 37.88 to 577.24 ± 59.91 nM. Also, these novel Schiff bases effectively inhibited α-glucosidase, with Ki values in the range of 1.56 ±

  摘要 本研究合成了八种新的席夫碱衍生物（2a-h），并研究了它们对乙酰胆碱酯酶（AChE）、丁酰胆碱酯酶（BChE）、α-葡萄糖苷酶和乳过氧化物酶（LPO）的抑制活性。使用 1 H 和 13 C 核磁共振 (NMR)、红外光谱 (IR) 和高分辨率质谱 (HRMS) 光谱方法表征合成化合物的结构。AChE 以低纳摩尔水平被这些新型希夫碱 (2a-h) 抑制，其 Ki 在 592.66 ± 57.04 和 810.78 ± 84.06 nM 之间不同。针对 BChE，新化合物的 Kis 从 358.31 ± 37.88 到 577.24 ± 59.91 nM 不等。此外，这些新型席夫碱有效抑制 α-葡萄糖苷酶，Ki 值范围为 1.56 ± 0.32 至 14.78 ± 2.57 nM。对于 LPO，Ki 值在 3.96 ± 0.37 至 12.75 ± 0.06 nM 的范围内。对于 α-葡萄糖苷酶，最有效的分子是
• Design, synthesis, biological evaluations and in silico studies of sulfonate ester derivatives of 2-(2-benzylidenehydrazono)thiazolidin-4-one as potential α-glucosidase inhibitors
  作者：Ramandeep Kaur、Rajnish Kumar、Nilambra Dogra、Ashok Kumar Yadav

  DOI：10.1016/j.molstruc.2021.131266

  日期：2022.1

  A novel series of hydrazolyl linked sulfonate ester analogues of 4-thiazolidinone nucleus has been rationally designed, synthesized and characterized by various spectroscopic techniques including 1H NMR, 13C NMR and mass spectrometry. All of the synthesized derivatives were tested for in vitro α-glucosidase inhibitory activities and antioxidant potential. The investigated compounds displayed appreciable

  合理设计、合成了一系列新型的4-噻唑烷酮核的肼基连接磺酸酯类似物，并通过1 H NMR、13 C NMR和质谱等多种光谱技术对其进行了表征。测试了所有合成衍生物的体外α-葡萄糖苷酶抑制活性和抗氧化潜力。与阿卡波糖 (478.07 ± 1.53 μM) 相比，所研究的化合物显示出明显的α-葡萄糖苷酶抑制作用，IC 50值范围为 42.80 ± 0.48 至 599.04 ± 1.26 μM，并建立了构效关系。此外，最有效的衍生物（7d) 在正常 HEK 细胞中通过 MTT 测定进行评估。体内双糖负荷试验证实（7d）比阿卡波糖（剂量为 20 mg/kg 体重）在降低蔗糖给药后餐后高血糖方面具有更高的功效。计算机程序，即同源建模、分子对接、分子动力学模拟、结合自由能计算和 ADME 预测研究进一步证明了体外和体内生物学研究的结果。
• Design and Synthesis of Pyridine and Thiazole Derivatives as Eco‐friendly Insecticidal to Control Olive Pests
  作者：Nadia A. A. Elkanzi、Aryam Khaled Ghayad Al‐Hazmi、Rania B. Bakr、Mohamed A. Gad、Hany M. Abd El‐Lateef、Ali M. Ali

  DOI：10.1002/cbdv.202300559

  日期：2023.7

  Treatment of p-tosyloxybenzaldehyde (1) with ethyl cyanoacetate afforded ethyl 2-cyano-3-(4-[(4-methylphenyl)sulfonyl]oxy}phenyl)acrylate (2) which reacted with some active methylene derivatives under microwave irradiation in presence of ammonium acetate yielded pyridine derivatives 3–7. On the other hand, when treatment of compound 1 with thiosemicarbazide gave 4-tosyloxybenzylidenethiosemicarbazone

  用氰基乙酸乙酯处理对甲苯磺酰氧基苯甲醛( 1 )，得到2-氰基-3-(4-[(4-甲基苯基)磺酰基]氧基}苯基)丙烯酸乙酯( 2 )，其在微波辐射下与一些活性亚甲基衍生物反应。乙酸铵存在下产生吡啶衍生物3 – 7。另一方面，当用氨基硫脲处理化合物1时，得到4-甲苯磺酰氧基苯亚甲基氨基硫脲( 8 ) ，它可以与一些活性亚甲基化合物反应，例如：溴乙酸乙酯、氯乙腈或苯甲酰溴衍生物，得到噻唑衍生物9-13。所有产物的结构均通过IR、 1 H-NMR、13 CNMR和质谱等元素和光谱分析证实。该方法的优点是反应时间短（3~7 min）、收率优异、产物纯净、加工成本低。在最后一类中，所有化合物的毒理学特征均针对Saissetia oleae（Olivier，1791）（半翅目：球虫科）进行了测试。关于 LC 50值。结果发现，与其他产品相比，化合物3具有最高的杀虫生物功效，对若虫和成虫的杀虫生物功效分别为0
• New iron(III), cobalt(II), nickel(II), copper(II), zinc(II) mixed-ligand complexes: Synthesis, structural, DFT, molecular docking and antimicrobial analysis
  作者：Hany M. Abd El-Lateef、Ali M. Ali、Mai M. Khalaf、Aly Abdou

  DOI：10.4314/bcse.v38i1.12

  日期：——

  The present framework has as its goal the design and synthesis and characterization of new mononuclear 1:1:1 (M:L:Q) mixed-ligand complexes, including FeLQ, CoLQ, NiLQ, CuLQ, and ZnLQ. The "L," is the 4-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)hydrazono]methylphenyl 4-methylbenzenesulfonate, while the "Q," is the 8-hydroxy quinoline. According to the findings, L and Q ligands each play the role of a neutral bi-dentate NN and a monobasic bi-dentate ON ligand, respectively. The findings demonstrated an octahedral shape. The density functional theory (DFT) technique was employed, and the quantum chemical descriptors were assessed, to optimize the molecular structure of the compounds. An in vitro investigation was carried out to investigate the antibacterial and antifungal activities of the compounds. According to the findings, the activity of metal complexes as potential candidates for use as antibiotics and antifungals is much greater than that of their free ligands. The in-silico inhibition of the 1fj4 protein was investigated using molecular docking. ZnLQ complex was the one that inhibited the 1fj4 protein with the greatest degree of success. The fact that this is the case lends credence to the notion that these compounds have the potential to function as launchpads for the development of new classes of antibiotics. KEY WORDS: Metal complexes, Schiff-base, Antimicrobial, DFT, Molecular docking Bull. Chem. Soc. Ethiop. 2024, 38(1), 147-166. DOI: https://dx.doi.org/10.4314/bcse.v38i1.12

  本框架的目标是设计、合成和表征新的单核 1:1:1 (M:L:Q) 混合配体复合物，包括 FeLQ、CoLQ、NiLQ、CuLQ 和 ZnLQ。其中 "L "是 4-[（4-氧代-4,5-二氢-1,3-噻唑-2-基）肼基]甲基苯基 4-甲基苯磺酸盐，而 "Q "是 8-羟基喹啉。根据研究结果，L 和 Q 配体分别扮演中性双齿 NN 和单碱性双齿 ON 配体的角色。研究结果显示了八面体形状。研究人员采用密度泛函理论（DFT）技术并评估了量子化学描述因子，以优化化合物的分子结构。对化合物的抗菌和抗真菌活性进行了体外研究。研究结果表明，作为抗生素和抗真菌剂的潜在候选化合物，金属复合物的活性远远高于其游离配体。研究人员使用分子对接法研究了 1fj4 蛋白的体内抑制作用。ZnLQ 复合物最成功地抑制了 1fj4 蛋白。事实证明，这些化合物具有开发新型抗生素的潜力； 关键词： 金属配合物 席夫碱 抗菌 DFT 分子对接 ； Bull.Chem.Soc.2024, 38(1), 147-166.DOI: https://dx.doi.org/10.4314/bcse.v38i1.12
• New Fe(III), Co(II), Ni(II), Cu(II), and Zn(II) mixed-ligand complexes: stractural, DFT, biological, and molecular docking studies
  作者：Hany M. Abd El-Lateef、Ali M. Ali、Mai M. Khalaf、Aly Abdou

  DOI：10.4314/bcse.v38i2.9

  日期：——

  The primary objective of the current framework was to synthesize novel mononuclear 1:1:1 complexes involving FeLG, CoLG, NiLG, CuLG, and ZnLG, where the ligand (L) is identified as 4-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)hydrazono]methylphenyl-4-methylbenzenesulfonate, and glycine (G) serves as the co-ligand. Comprehensive characterization of the investigated complexes was achieved through various analytical techniques, including FTIR, UV-Vis spectroscopy, elemental analysis, mass spectra, magnetic susceptibility measurements, molar conductivity assessments, and thermogravimetric analysis (TGA). The determination of stoichiometry was performed employing the molar ratio technique, revealing the octahedral geometry inherent in the isolated metal complexes. Employing a density functional theory (DFT) approach, the molecular structures of the designated compounds were theoretically elevated, and quantum chemical descriptors were derived to provide a deeper insight into their electronic properties. Furthermore, the inhibitory potential of these compounds against fungal strains and pathogenic bacteria prevalent in the Arab environment was evaluated using the disc diffusion method, emphasizing their role in combating diseases affecting humans, animals, and plants. Notably, the metal complexes exhibited superior antibacterial activity, as evidenced by a higher activity index. Molecular docking investigations were conducted to ascertain the inhibitory effects of the compounds on the 1FJ4 protein, with ZnLG emerging as the compound with the highest binding affinity. These results suggest the promising candidacy of these compounds as antimicrobial agents, particularly in the context of combating bacterial and fungal infections. KEY WORDS: Complexes, Antimicrobial, DFT, Schiff base, Molecular docking Bull. Chem. Soc. Ethiop. 2024, 38(2), 397-416.                                                               DOI: https://dx.doi.org/10.4314/bcse.v38i2.9

  当前框架的主要目标是合成涉及 FeLG、CoLG、NiLG、CuLG 和 ZnLG 的新型单核 1:1:1 复合物，其中配体（L）被确定为 4-[(4-氧代-4,5-二氢-1,3-噻唑-2-基)肼基]甲基苯基-4-甲基苯磺酸盐，甘氨酸（G）作为辅助配体。通过各种分析技术，包括傅立叶变换红外光谱、紫外可见光谱、元素分析、质谱、磁感应强度测量、摩尔电导率评估和热重分析（TGA），对所研究的复合物进行了全面的表征。利用摩尔比率技术确定了化学计量，揭示了分离金属复合物固有的八面体几何结构。利用密度泛函理论（DFT）方法，对指定化合物的分子结构进行了理论升华，并得出了量子化学描述符，从而对其电子特性有了更深入的了解。此外，还利用圆盘扩散法评估了这些化合物对阿拉伯环境中流行的真菌菌株和致病细菌的抑制潜力，强调了它们在防治影响人类、动物和植物的疾病方面的作用。值得注意的是，金属复合物表现出了更高的抗菌活性，其活性指数也更高。分子对接研究确定了化合物对 1FJ4 蛋白的抑制作用，其中 ZnLG 成为结合亲和力最高的化合物。这些结果表明，这些化合物有望成为抗菌剂，尤其是在抗击细菌和真菌感染方面； 关键词：配合物，抗菌，DFT，席夫碱，分子对接 ； Bull.Chem.Soc.2024, 38(2), 397-416. ； DOI: https://dx.doi.org/10.4314/bcse.v38i2.9