Synthesis, characterization, anti-proliferative evaluation, and molecular docking study of some new N-(1, 3-dioxoisoindolin-4-yl)acetamide derivatives,Journal of Heterocyclic Chemistry

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Synthesis, characterization, anti-proliferative evaluation, and molecular docking study of some new N-(1, 3-dioxoisoindolin-4-yl)acetamide derivatives
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2023-07-23 , DOI: 10.1002/jhet.4714
Hanuman Narode ₁ , Manoj Gayke ₁ , Rajesh S. Bhosale ₁ , Kiran R. Kharat _{2,

3} , Rajendra Pawar ₄ , Jhillu Singh Yadav ₁

Affiliation

A series of new N-(1,3-dioxoisoindolin-4-yl)acetamide derivatives were designed and synthesized via a condensation reaction between N-(1,3-dioxo-1,3-dihydro isobenzofuran-4-yl)acetamide and various aliphatic and aromatic amines in water as an environmentally friendly solvent. All synthesized compounds (NPD 1–14) molecular structure was confirmed by their FTIR, ¹H NMR, ¹³C NMR, and mass spectroscopy. The final target compounds were screened for their in vitro antiproliferative activity by taking 5-Fluorouracil (5-FU) as a reference drug. Among 14 newly synthesized compounds, five compounds were shown to be effectively cytotoxic against the MCF7 cells. In comparison to the standard medication drug 5-FU (CC₅₀ = 11.219 ± 0.847), the synthesized compounds NPD-8 (CC₅₀ = 16.14 ± 2.08 μM) and NPD-12 (CC₅₀ = 11.26 ± 1.158 μM) demonstrated the most active against the MCF7 cells. Furthermore, in silico study was performed to find molecular level interaction of active compounds with anticancer drug target enzyme NUDT5 inhibitors block hormone signaling in breast cancer cells. The compound NPD-12 showed the highest molecular binding energy −8.3 kcal/mol which interacted more effectively than the reference drug 5-FU binding energy −4.6 kcal/mol. These synthesized N-(1,3-dioxoisoindolin-4-yl) acetamide derivatives have been identified as a potential class of chemicals for further research as plausible new anticancer entities.

中文翻译：

一些新型N-(1, 3-二氧异吲哚啉-4-基)乙酰胺衍生物的合成、表征、抗增殖评价及分子对接研究

通过N-(1,3-二氧代-1,3-二氢异苯并呋喃-4-基)乙酰胺和各种脂肪族和芳香族胺在水中作为环保溶剂。^{所有合成的化合物 (NPD 1–14) 分子结构均通过 FTIR、 1} H NMR、¹³ C NMR 和质谱法确认。以5-氟尿嘧啶（5-FU）为参比药，筛选最终目标化合物的体外抗增殖活性。在 14 种新合成的化合物中，有 5 种化合物被证明对 MCF7 细胞具有有效的细胞毒性。与标准药物 5-FU (CC ₅₀ = 11.219 ± 0.847)，合成的化合物 NPD-8 (CC ₅₀ = 16.14 ± 2.08 μM) 和 NPD-12 (CC ₅₀ = 11.26 ± 1.158 μM) 对 MCF7 细胞最具活性。此外，还进行了计算机模拟研究，以发现活性化合物与抗癌药物靶酶 NUDT5 抑制剂在分子水平上的相互作用，阻断乳腺癌细胞中的激素信号传导。化合物NPD-12显示出最高的分子结合能-8.3 kcal/mol，其相互作用比参考药物5-FU结合能-4.6 kcal/mol更有效。这些合成的 N-(1,3-二氧异吲哚啉-4-基) 乙酰胺衍生物已被确定为一类潜在的化学品，可作为可能的新抗癌实体进行进一步研究。

更新日期：2023-07-23

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