Abstract

A series of novel trienone curcumin analogues 1, based on Claisen–Schmidt condensations of cinnamaldehyde, arylaldehyde, and acetone, is prepared and the crystal structure of 1a is determined by single crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P2₁/c with a = 18.120(5) Å, b = 14.624(4) Å, c = 5.8926(16) Å, β = 97.686(3)°, Z = 4, V = 1547.3(7) Å³, D_c = 1.265 mg/m³, μ = 0.243 mm^–1, F(000) = 616, final R = 0.0449 and wR = 0.1109 for 2156 observed reflections (I > 2σ(I)). In addition, molecular docking of compounds 1a, 1d and IKKβ protein are performed in CDOCKER of Discovery Studio 4.5 and the three-dimensional crystal structures of the cancer factor-human kinase-β enzyme IKKβ (PDB: 4KIK) are obtained. Furthermore, the antitumor activities of 1a and 1d are evaluated by the CCK-8 assay against human cancer cell line A549 in vitro, indicating that the small molecules have a moderate antitumor activity.

中文翻译：

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来自肉桂醛的新型姜黄素类似物的合成、晶体结构和生物活性

摘要

制备了一系列基于肉桂醛、芳醛和丙酮的 Claisen-Schmidt 缩合的新型三烯酮姜黄素类似物 1，并通过单晶 X 射线衍射确定了1a的晶体结构。该晶体属于单斜晶系，空间群P 2 ₁ / c，a  = 18.120(5) Å, b  = 14.624(4) Å, c  = 5.8926(16) Å, β = 97.686(3)°, Z  = 4, V  = 1547.3(7) Å ³ , D _c  = 1.265 mg/m ³ , μ = 0.243 mm ^–1 , F (000) = 616, 最终R = 0.0449 和wR  = 0.1109 对于 2156 个观察到的反射 ( I  > 2σ( I ))。此外，在Discovery Studio 4.5的CDOCKER中进行化合物1a、1d和IKKβ蛋白的分子对接，得到癌因子-人激酶-β酶IKKβ（PDB：4KIK）的三维晶体结构。此外，通过体外抗人癌细胞系 A549 的 CCK-8 试验评估了1a和1d的抗肿瘤活性，表明小分子具有中等抗肿瘤活性。