Green synthesis of 2,4-dinitro-substituted bischalcones using bifunctional magnetic nanocatalyst

IF 1.3 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Main Group Chemistry Pub Date : 2023-02-14 DOI:10.3233/mgc-220085
A. Doroudi, Raziye Saeidi Rashk Oliaei, L. Khorsandi, M. T. Tahmasebi Birgani, Amanollah Zarei Ahmady
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Abstract

Flavonoids have many biological properties, such as anticancer activity. Chalcones, one of their subunits, attribute their biological activity to their enone part. The presence of dinitrophenyl group in bischalcone because of its radiosensitivity property is important. Radiosensitivity property reduces radiation time in cancer patients and reduces damage to their healthy tissues. In this regard, 2,4-dinitrophenyl bischalcones were synthesized. The presence of 2,4-dinitrobenzaldehyde as a fixed component in synthesis pathway, leads to a reduction in yield of synthesis by common catalysts. Therefore, in this study, for bis-chalone synthesis, we used Graphene Oxide/Fe3O4/L-Proline nanocomposite as a green recoverable bifunctional organocatalyst. This catalyst was recovered simply by applying an external magnet and reused for eight runs. In this research, chalcones and asymmetric bis-chalcones have been synthesized with diverse substitutes in high yields (78–97%). Also, short reaction times (10–82 min), and simple experimental procedures with easy work-up are advantages of the introduced procedure. The synthesized compounds were characterized by melting point and analytical techniques. The chemical structures of synthesized compounds were confirmed by means of IR, 1HNMR, and 13CNMR.
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利用双功能磁性纳米催化剂绿色合成2,4-二硝基取代双查尔酮
黄酮类化合物具有许多生物学特性,如抗癌活性。查尔酮是其亚基之一,其生物活性归因于其烯酮部分。双查尔酮中二硝基苯基的存在对其放射敏感性具有重要意义。放射敏感性减少了癌症患者的辐射时间,减少了对其健康组织的损害。在此基础上合成了2,4-二硝基苯双查尔酮。2,4-二硝基苯甲醛作为固定组分存在于合成途径中,导致普通催化剂合成产率降低。因此,在本研究中,我们使用氧化石墨烯/Fe3O4/ l -脯氨酸纳米复合材料作为绿色可回收双功能有机催化剂来合成双氯酮。该催化剂仅通过施加外部磁铁即可回收,并重复使用了8次。本研究以不同的取代物合成了查尔酮和不对称双查尔酮,收率高达78-97%。此外,该方法的优点是反应时间短(10-82分钟),实验程序简单,易于操作。用熔点和分析技术对合成的化合物进行了表征。合成化合物的化学结构通过IR、1HNMR和13CNMR进行了确证。
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来源期刊
Main Group Chemistry
Main Group Chemistry 化学-化学综合
CiteScore
2.00
自引率
26.70%
发文量
65
审稿时长
>12 weeks
期刊介绍: Main Group Chemistry is intended to be a primary resource for all chemistry, engineering, biological, and materials researchers in both academia and in industry with an interest in the elements from the groups 1, 2, 12–18, lanthanides and actinides. The journal is committed to maintaining a high standard for its publications. This will be ensured by a rigorous peer-review process with most articles being reviewed by at least one editorial board member. Additionally, all manuscripts will be proofread and corrected by a dedicated copy editor located at the University of Kentucky.
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