Ren Haitao, Qi Fan, Zhao Yuzhen, Labidi Abdelkader, Miao Zongcheng
Technological Institute of Materials & Energy Science (TIMES), Xijing University, Xi'an 710123, China.
State Key Laboratory of Medicinal Chemical, College of Pharmacy, Nankai University, Tianjin 300071, China.
Molecules. 2024 Oct 4;29(19):4702. doi: 10.3390/molecules29194702.
A novel ()-1-(4-methylbenzylidene)-4-(3-isopropylphenyl) thiosemicarbazone was synthesized in a one-pot four-step synthetic route. Fourier transform infrared spectroscopy (FTIR), H and C nuclear magnetic resonances (NMR), single-crystal X-ray diffraction, and UV-visible absorption spectroscopy were utilized to confirm the successful preparation of the title compound. Single-crystal data indicated that the intramolecular hydrogen bond N(3)-H(3)···N(1) and intermolecular hydrogen bond N(2)-H(2)···S(1) (1 - x, 1 - y, 1 - z) existed in the crystal structure and packing of the title compound. Besides the covalent interaction, the non-covalent weak intramolecular hydrogen bond N(3)-H(3)···N(1) discussed by atoms in molecules (AIM) theory also functioned in maintaining the title compound's crystal structure. The strong intermolecular hydrogen bond N(2)-H(2)···S(1) (1 - x, 1 - y, 1 - z) discussed by Hirshfeld surface analysis played a major role in maintaining the title compound's crystal packing. The local maximum and minimum electrostatic potential of the title compound was predicted by electrostatic potential (ESP) analysis. The UV-visible spectra and HOMO-LUMO analysis revealed that the title compound has a low Δ energy gap (3.86 eV), which implied its high chemical reactivity due to the easy occurrence of charge transfer interactions within the molecule. Molecular docking and in vitro antifungal assays evidenced that its antifungal activity is comparable to the reported , indicating its usage as a potential candidate for future antifungal drugs.
通过一锅四步合成路线合成了一种新型的()-1-(4-甲基亚苄基)-4-(3-异丙基苯基)硫代氨基脲。利用傅里叶变换红外光谱(FTIR)、氢和碳核磁共振(NMR)、单晶X射线衍射以及紫外可见吸收光谱来确认标题化合物的成功制备。单晶数据表明，在标题化合物的晶体结构和堆积中存在分子内氢键N(3)-H(3)···N(1)和分子间氢键N(2)-H(2)···S(1)(1 - x, 1 - y, 1 - z)。除了共价相互作用外，分子中的原子(AIM)理论所讨论的非共价弱分子内氢键N(3)-H(3)···N(1)也在维持标题化合物的晶体结构中发挥作用。Hirshfeld表面分析所讨论的强分子间氢键N(2)-H(2)···S(1)(1 - x, 1 - y, 1 - z)在维持标题化合物的晶体堆积中起主要作用。通过静电势(ESP)分析预测了标题化合物的局部最大和最小静电势。紫外可见光谱和HOMO-LUMO分析表明，标题化合物具有较低的Δ能隙(3.86 eV)，这意味着由于分子内电荷转移相互作用容易发生，其具有较高的化学反应活性。分子对接和体外抗真菌试验证明其抗真菌活性与报道的相当，表明其作为未来抗真菌药物的潜在候选物的用途。
