Syn-Propanethial S-Oxide as an Available Natural Building Block for the Preparation of Nitro-Functionalized, Sulfur-Containing Five-Membered Heterocycles: An MEDT Study.

IF 4.2 2区化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Molecules Pub Date : 2024-10-15 DOI:10.3390/molecules29204892

Mikołaj Sadowski, Ewa Dresler, Karolina Zawadzińska, Aneta Wróblewska, Radomir Jasiński

引用次数: 0

Abstract

The regio- and stereoselectivity and the molecular mechanisms of the [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and selected conjugated nitroalkenes were explored theoretically in the framework of the Molecular Electron Density Theory. It was found that cycloadditions with the participation of nitroethene as well as its methyl- and chloro-substituted analogs can be realized via a single-step mechanism. On the other hand, [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and 1,1-dinitroethene can proceed according to a stepwise mechanism with a zwitterionic intermediate. Finally, we evaluated the affinity of model reaction products for several target proteins: cytochrome P450 14α-sterol demethylase CYP51 (RSCB Database PDB ID: 1EA1), metalloproteinase gelatinase B (MMP-9; PDB ID: 4XCT), and the inhibitors of cyclooxygenase COX-1 (PDB:3KK6) and COX-2 (PDB:5KIR).

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作为制备硝基官能化、含硫五元杂环的可用天然构件的合成丙硫醚 S-氧化物：MEDT 研究。

在分子电子密度理论的框架内，从理论上探讨了辛-丙硫醚 S-氧化物与选定的共轭硝基烯之间的 [3 + 2] 环加成反应的区域和立体选择性以及分子机理。研究发现，硝基乙烯及其甲基和氯代类似物参与的环加成反应可以通过单步机理实现。另一方面，Syn-propanethial S-氧化物和 1,1-二硝基乙烯之间的[3+2]环加成反应可以通过一个具有齐聚物中间体的分步机理进行。最后，我们评估了模型反应产物对几种靶蛋白的亲和力：细胞色素 P450 14α-sterol demethylase CYP51（RSCB 数据库 PDB ID：1EA1）、金属蛋白酶明胶酶 B（MMP-9；PDB ID：4XCT）以及环氧化酶 COX-1 （PDB:3KK6）和 COX-2 （PDB:5KIR）的抑制剂。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Molecules 化学-有机化学

CiteScore

7.40

自引率

8.70%

发文量

7524

审稿时长

1.4 months

期刊介绍： Molecules (ISSN 1420-3049, CODEN: MOLEFW) is an open access journal of synthetic organic chemistry and natural product chemistry. All articles are peer-reviewed and published continously upon acceptance. Molecules is published by MDPI, Basel, Switzerland. Our aim is to encourage chemists to publish as much as possible their experimental detail, particularly synthetic procedures and characterization information. There is no restriction on the length of the experimental section. In addition, availability of compound samples is published and considered as important information. Authors are encouraged to register or deposit their chemical samples through the non-profit international organization Molecular Diversity Preservation International (MDPI). Molecules has been launched in 1996 to preserve and exploit molecular diversity of both, chemical information and chemical substances.