Chemistry Department, Faculty of Science, Ain Shams University, 11566, Cairo, Egypt.
Pesticide Chemistry Department, Chemical Industries Research Institute, National Research Centre, 12622, Cairo, Egypt.
Chem Biodivers. 2024 Oct;21(10):e202401023. doi: 10.1002/cbdv.202401023. Epub 2024 Sep 9.
A set of novel naphthalene derivatives was synthesized via investment of the electrophilic reaction center of the easily obtainable starting substance, 2-cyano-3-(naphthalen-1-yl)acryloyl chloride (1), with various nitrogen nucleophiles and assessed as potential antitumor agents. The chemical structures of these derivatives were completely specified using several spectral and elemental analyses. The antiproliferative efficacy of the discovered compounds against the human cancer cell lines HepG2 and MCF-7 was investigated. Compounds 12b and 9 have more potent anticancer activity versus MCF-7 breast cancer. DFT calculations for the synthesized compounds were studied to determine molecular geometry, frontier orbital analysis, and molecular electrostatic potential. Compound 2 has the lowest energy gap, the highest softness, and the lowest hardness molecule. Also, the electrophilicity values of the studied molecules provide evidence for their biological effectiveness, as compound 9 had significant antiproliferative activity and a high value of electrophilicity (ω) (0.190 eV).
一组新型萘衍生物是通过引入易得起始物质 2-氰基-3-(萘-1-基)丙烯酰氯（1）的亲电反应中心，与各种氮亲核试剂进行反应合成的，并被评估为潜在的抗肿瘤药物。这些衍生物的化学结构完全通过几种光谱和元素分析来确定。研究了发现的化合物对人肝癌细胞系 HepG2 和 MCF-7 的增殖抑制活性。化合物 12b 和 9 对 MCF-7 乳腺癌具有更强的抗癌活性。对合成化合物进行了 DFT 计算，以确定分子几何形状、前沿轨道分析和分子静电势。化合物 2 具有最低的能隙、最高的软度和最低的硬度分子。此外，研究分子的电负性值为它们的生物有效性提供了证据，因为化合物 9 具有显著的增殖抑制活性和高电负性值（ω）（0.190 eV）。
