Crystal structure of 3-methyl-2,6-diphenyl-1-(2-thiocyanatoacetyl)piperidin-4-one: A combined experimental and theoretical study

IF 2.218 Q2 Chemistry

Chemical Data Collections Pub Date : 2025-01-28 DOI:10.1016/j.cdc.2025.101183

Karthiga A． R , Divyabharathi S , Reshwen Shalo R , Rajeswari K , Vidhyasagar T

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Abstract

The structure of 3-methyl-2,6-diphenyl-1-(2-thiocyanatoacetyl)piperidin-4-one (3) was elucidated through single-crystal X-ray diffraction, revealing a distorted boat conformation of the piperidine ring. Phenyl and methyl groups occupy equatorial positions, with another phenyl group positioned axially. Molecular packing is stabilized by C–H⋯N, C–H⋯O and C–H⋯π interactions. DFT optimization at the B3LYP/6–311++G(d, p) level showed excellent agreement with experimental geometry, validating the model. HOMO-LUMO analysis revealed the electronic properties, while Mulliken charge and MEP identified reactivity and binding sites. Hirshfeld surface analysis quantified intermolecular interactions, highlighting H⋯H contacts (41.8 %), with energy framework analysis emphasizing dispersion forces. Docking studies with 3ERT protein demonstrated favorable interactions, supporting its anticancer potential. ADME predictions confirmed a suitable pharmacokinetic profile, underscoring its drug development potential. This study integrates crystallographic, computational, and biological evaluations showcasing the structural and therapeutic significance of the compound.

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3-甲基-2,6-二苯基-1-（2-硫氰酸乙酰基）胡椒碱-4- 1晶体结构的实验与理论结合研究

通过单晶x射线衍射对3-甲基-2,6-二苯基-1-（2-硫氰酸乙酰基）哌啶-4- 1(3)的结构进行了解析，发现哌啶环呈扭曲的船形构象。苯基和甲基占据赤道位置，另一个苯基在轴向位置。分子堆积由C-H⋯N、C-H⋯O和C-H⋯π相互作用稳定。B3LYP/ 6-311 ++G（d, p）水平的DFT优化结果与实验几何形状吻合良好，验证了模型的正确性。HOMO-LUMO分析揭示了电子性质，Mulliken电荷和MEP分析确定了反应性和结合位点。Hirshfeld表面分析量化了分子间的相互作用，突出了H⋯H接触（41.8%），能量框架分析强调了色散力。与3ERT蛋白的对接研究显示了良好的相互作用，支持其抗癌潜力。ADME预测证实了合适的药代动力学特征，强调了其药物开发潜力。本研究综合了晶体学、计算学和生物学评价，展示了该化合物的结构和治疗意义。

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来源期刊

Chemical Data Collections Chemistry-Chemistry (all)

CiteScore

6.10

自引率

0.00%

发文量

169

审稿时长

24 days

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