N-Silylmethyl-2-(1-Naphthyl)Acetamides: Synthesis, Structure and Computational Screening

IF 1.7 3区化学 Q3 CHEMISTRY, ORGANIC

Current Organic Chemistry Pub Date : 2024-05-13 DOI:10.2174/0113852728296495240409062733

A. Soldatenko, M. Molokeev, N. Lazareva

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Abstract

Synthesis of new hybrid organosilicon compounds based on the amides 1-naphthylacetic acid was described. N-Organyl-2-(1-naphthyl)-N-[(triethoxysilyl) methyl]acetamides were obtained by the reaction of 1- naphthylacetyl chloride with α-silylamines RNHCH2Si(OEt)3 (R = Me, i-Pr and Ph). Their subsequent interaction with N(CH2CH2OH)3 led to the formation of N-organyl-2-(1-naphthyl)-N-(silatranylmethy) acetamides. The structure of these hybrid compounds wascharacterized by 1H, 13C, and 29Si NMR spectroscopy. The structure of N-methyl- and N-isopropyl-2-(1-naphthyl)-N-(silatranylmethy)acetamides was confirmed by X-ray diffraction analysis. Results of computational screening showed that these silatranes are bioavailable and have drug-likeness. Silatranes XSi(OCHRCH2)3N belong to a widely known class of pentacoordinated silicon compounds with intramolecular dative bond Si←N. Their unique structure in combination with properties of the X substituent provide high and diverse physiological and pharmacological activities: immunomodulatory, antitumor, growth stimulating, antimicrobial and other]. Over the last 15 years, several papers have been published on the study of growth-regulating activity of compounds containing silatranyl group. However, there is no systematic study of phytohormones containing the silicon group in the molecule. N-organyl-2-(1-naphthyl)-N-(silylmethyl)acetamides NMR spectroscopy, X-ray diffraction analysis, computational screening, PASS, ADME

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N-硅甲基-2-(1-萘基)乙酰胺：合成、结构和计算筛选

介绍了基于 1-萘乙酸酰胺的新型杂化有机硅化合物的合成。通过 1-萘乙酰氯与 α-硅胺 RNHCH2Si(OEt)3（R = Me、i-Pr 和 Ph）反应，得到了 N-芳基-2-（1-萘基）-N-[（三乙氧基硅基）甲基]乙酰胺。这些混合化合物的结构通过 1H、13C 和 29Si NMR 光谱进行了表征。通过 X 射线衍射分析确认了 N-甲基和 N-异丙基-2-(1-萘基)-N-(硅杂戊基甲基)乙酰胺的结构。计算筛选结果表明，这些硅烷具有生物可利用性和药物相似性。硅烷 XSi(OCHRCH2)3N 属于广为人知的五配位硅化合物，具有分子内双键 Si←N。它们的独特结构与 X 取代基的特性相结合，具有高度和多样化的生理和药理活性：免疫调节、抗肿瘤、刺激生长、抗菌等]。在过去的 15 年中，发表了多篇关于含硅烷基化合物生长调节活性研究的论文。N-芳基-2-（1-萘基）-N-（硅甲基）乙酰胺NMR 光谱、X 射线衍射分析、计算筛选、PASS、ADME

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来源期刊

Current Organic Chemistry 化学-有机化学

CiteScore

3.70

自引率

7.70%

发文量

审稿时长

1 months

期刊介绍： Current Organic Chemistry aims to provide in-depth/mini reviews on the current progress in various fields related to organic chemistry including bioorganic chemistry, organo-metallic chemistry, asymmetric synthesis, heterocyclic chemistry, natural product chemistry, catalytic and green chemistry, suitable aspects of medicinal chemistry and polymer chemistry, as well as analytical methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by chosen experts who are internationally known for their eminent research contributions. The Journal also accepts high quality research papers focusing on hot topics, highlights and letters besides thematic issues in these fields. Current Organic Chemistry should prove to be of great interest to organic chemists in academia and industry, who wish to keep abreast with recent developments in key fields of organic chemistry.