Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents

IF 1.3 3区 化学 Q3 CHEMISTRY, ORGANIC Heterocyclic Communications Pub Date : 2023-01-01 DOI:10.1515/hc-2022-0162
Robert B. Smith, William Roberts, M. Upenieks, M. Gibson, Michael T. Wentzel, Kyle A. Grice, S. Zingales
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Abstract

Abstract Natural products and their analogs have been explored to stop the progression of cancer cells without unwanted side effects. Chalcones, compounds synthesized naturally in plants, have demonstrated potential as anti-cancer treatments. A library of bis-chalcones that are similar in structure to EF-24, a bis-chalcone molecule known to have anti-cancer properties, has been synthesized in order to examine their medicinal properties. This report highlights the synthesis of ten novel analogs, their anti-cancer activities, and conformational analysis via cryo-NMR and corroboration by density functional theory calculations of the lead compound 1b, tert-butyl 3,5-bis((E)-4-methylbenzylidene)-4-oxopiperidine-1-carboxylate.
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n - boc保护的-3,5-双(芳基)-4-哌酮EF-24类似物的合成及构象分析
天然产物及其类似物已被探索以阻止癌细胞的进展而没有不必要的副作用。查尔酮,一种在植物中自然合成的化合物,已被证明具有抗癌治疗的潜力。为了研究其药用特性,已经合成了一个与EF-24(一种已知具有抗癌特性的双查尔酮分子)结构相似的双查尔酮文库。本报告重点介绍了10种新型类似物的合成及其抗癌活性,并通过低温核磁共振分析和密度泛函理论计算证实了先导化合物1b,叔丁基3,5-二((E)-4-甲基苄基)-4-氧哌替啶-1-羧酸酯。
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来源期刊
Heterocyclic Communications
Heterocyclic Communications 化学-有机化学
CiteScore
3.80
自引率
4.30%
发文量
13
审稿时长
1.4 months
期刊介绍: Heterocyclic Communications (HC) is a bimonthly, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.
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