Abstract In this report, 3-((4,6-dimethylpyrimidin-2-yl)amino)isobenzofuran-1(3H)-one have been synthesized via reaction between phthalaldehydic acid and 2-amino-4,6-dimethylpyrimidine in 90% yields and characterized by Infrared (IR), Nuclear Magnetic Resonance (NMR), Ultraviolet–visible (UV–Vis), X-ray single crystal diffraction techniques. The single-crystal X-ray analysis shows that the title compound crystallizes in the triclinic space group P-1 with unit-cell parameters a = 7.9351(4) A, b = 11.1687(6) A, c = 16.1281(9) A, α = 73.713(5)°, β = 80.362(5)°, γ = 72.882(4)° and Z = 4. A theoretical study with hybrid functional B3LYP 6-311G (d, p) basis set have been used in calculations. The structural and electronic properties have been detailed. The title compound was screened for its antioxidant activity by (1,1-diphenyl-2-picryl hydrazyl) free radical scavenging (DPPH), Ferric ion reducing antioxidant power (FRAP), total phenolic contents (TP) assays and its ferrous ions chelating property. Electronic absorption titration, thermal denaturation measurement and viscosity techniques were used to determine the interaction between double stranded DNA (dsDNA) and compound 1. In three techniques, the mode of binding of compound 1 to dsDNA is minor groove. The UV–Vis measurement results allowed the calculation of the binding constant showing the binding strength of compound 1 to dsDNA was calculated as 8.13 × 104 ± 0.07 L mol−1. Moreover, the molecular docking calculations have been performed to investigate the compound–DNA interactions, computationally. In molecular docking calculations, it was observed that for the title compound, the lowest energy docking pose takes place in the minor groove of DNA and in addition to minor groove binding, interactions between the compound and the consecutive base pairs of DNA which may cause a partial intercalation were also observed. Results showed that title compound – DNA complex is stabilized by several hydrogen bonds, and Pi-alkyl interactions also take part in the stabilization of the complex. Binding affinities of the lowest energy docking pose of the title compound was found to be −8.3 kcal/mol.

中文翻译：

---

新型3-((4,6-二甲基嘧啶-2-基)氨基)异苯并呋喃-1(3H)-one的晶体结构研究及相关理论研究

摘要 本报告通过邻苯二甲酸与 2-氨基-4,6-二甲基嘧啶 90% 反应合成了 3-((4,6-二甲基嘧啶-2-基)氨基)异苯并呋喃-1(3H)-酮。产率并通过红外 (IR)、核磁共振 (NMR)、紫外-可见 (UV-Vis)、X 射线单晶衍射技术表征。单晶 X 射线分析表明，标题化合物在三斜空间群 P-1 中结晶，晶胞参数 a = 7.9351(4) A, b = 11.1687(6) A, c = 16.1281(9) A , α = 73.713(5)°, β = 80.362(5)°, γ = 72.882(4)° and Z = 4. 混合泛函 B3LYP 6-311G (d, p) 基组的理论研究已用于计算。已经详细描述了结构和电子特性。通过以下方法筛选标题化合物的抗氧化活性 (1, 1-diphenyl-2-picryl hydrazyl) 自由基清除 (DPPH)、铁离子还原抗氧化能力 (FRAP)、总酚含量 (TP) 测定及其亚铁离子螯合特性。使用电子吸收滴定、热变性测量和粘度技术来确定双链 DNA (dsDNA) 与化合物 1 之间的相互作用。在三种技术中，化合物 1 与 dsDNA 的结合方式是小沟。UV-Vis 测量结果允许计算结合常数，显示化合物 1 与 dsDNA 的结合强度计算为 8.13 × 104 ± 0.07 L mol-1。此外，已经进行了分子对接计算以通过计算研究化合物-DNA 相互作用。在分子对接计算中，观察到对于标题化合物，最低能量对接姿势发生在 DNA 的小沟中，除了小沟结合之外，还观察到化合物与 DNA 的连续碱基对之间的相互作用，这可能导致部分嵌入。结果表明，标题化合物-DNA 复合物由几个氢键稳定，π-烷基相互作用也参与了复合物的稳定。发现标题化合物的最低能量对接姿势的结合亲和力为 -8.3 kcal/mol。和π-烷基相互作用也参与了配合物的稳定。发现标题化合物的最低能量对接姿势的结合亲和力为 -8.3 kcal/mol。和π-烷基相互作用也参与了配合物的稳定。发现标题化合物的最低能量对接姿势的结合亲和力为 -8.3 kcal/mol。