Abozeid Mohamed Ahmed, El-Sawi Aya Atef, Elmorsy Mohamed Ramadan, Abdelmoteleb Mohamed, Hassan Abdel-Rahman Abdel-Rahman, Ibrahim El-Desoky El-Sayed
Department of Chemistry, Faculty of Science, Mansoura University Mansoura-35516 Egypt
Food Allergy Research & Resource Program (FARRP), Department of Food Science & Technology, University of Nebraska Lincoln NE USA.
RSC Adv. 2019 Sep 6;9(48):27996-28005. doi: 10.1039/c9ra05154f. eCollection 2019 Sep 3.
A new promising protocol has been developed for the synthesis of scarce oxocine derivatives 3a-e and 6 through addition of amine-based nucleophiles such as hydroxylamine hydrochloride, primary amine and hydrazide to chromonylidene benzothiazol-2-ylacetonitrile 2 in refluxing dioxane under metal free reaction conditions in moderate to good yields. Other nitrogen nucleophiles such as piperidine, hydrazine and thiosemicarbazide failed to afford the corresponding oxocinols, and instead pyridine derivatives 7, 8 and 10 were obtained exclusively. Predictive study for the biological activities using PASS (prediction of activity spectra for biologically active substances) online software showed optimistic activities for oxocinols 3a-e in the treatment of cancer, influenza A and microbial infections. Additionally, DFT studies of oxocine derivatives 3a-e and 6 indicated the presence of required thermodynamics parameters for the application in dye-sensitized solar cells (DSSCs).
通过在无金属反应条件下，于回流的二氧六环中，将基于胺的亲核试剂（如盐酸羟胺、伯胺和酰肼）添加到亚铬酰基苯并噻唑 -2- 基乙腈 2 中，已经开发出一种新的有前景的方案，用于合成稀有的氧杂环辛烷衍生物 3a - e 和 6，产率适中至良好。其他氮亲核试剂（如哌啶、肼和硫代氨基脲）未能得到相应的氧杂环辛醇，而是仅得到吡啶衍生物 7、8 和 10。使用 PASS（生物活性物质活性谱预测）在线软件对生物活性进行的预测研究表明，氧杂环辛醇 3a - e 在治疗癌症、甲型流感和微生物感染方面具有乐观的活性。此外，对氧杂环辛烷衍生物 3a - e 和 6 的 DFT 研究表明，它们存在用于染料敏化太阳能电池（DSSC）应用所需的热力学参数。
