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Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine.

ABSTRACT: The data on the synthesis of N-aminomorpholine hydrazones are presented. It is shown that the interaction of N-aminomorpholine with functionally substituted benzaldehydes and 4-pyridinaldehyde in isopropyl alcohol leads to the formation of corresponding hydrazones. The structure of the synthesized compounds was studied by ¹H and ¹³C NMR spectroscopy methods, including the COSY (¹H-¹H), HMQC (¹H-¹³C) and HMBC (¹H-¹³C) methodologies. The values of chemical shifts, multiplicity, and integral intensity of ¹H and ¹³C signals in one-dimensional NMR spectra were determined. The COSY (¹H-¹H), HMQC (¹H-¹³C), and HMBC (¹H-¹³C) results revealed homo- and heteronuclear interactions, confirming the structure of the studied compounds. The antiviral, cytotoxic, and antimicrobial activity of some synthesized hydrazones were investigated. It is shown that 2-((morpholinoimino)methyl)benzoic acid has a pronounced viral inhibitory property, comparable in its activity to commercial drugs Tamiflu and Remantadine. A docking study was performed using the influenza virus protein models (1930 Swine H1 Hemagglutinin and Neuraminidase of 1918 H1N1 strain). The potential binding sites that are complementary with 2-((morpholinoimino)methyl)benzoic acid were found.

SUBMITTER: Nurkenov OA

PROVIDER: S-EPMC11314140 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature

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Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine.

Nurkenov Oralgazy A OA Zhautikova Saule B SB Khlebnikov Andrei I AI Syzdykov Ardak K AK Fazylov Serik D SD Seilkhanov Tulegen M TM Kabieva Saule K SK Turdybekov Kobylandy M KM Mendibayeva Anel Z AZ Zhumanazarova Gaziza M GM

Molecules (Basel, Switzerland) 20240730 15

The data on the synthesis of N-aminomorpholine hydrazones are presented. It is shown that the interaction of N-aminomorpholine with functionally substituted benzaldehydes and 4-pyridinaldehyde in isopropyl alcohol leads to the formation of corresponding hydrazones. The structure of the synthesized compounds was studied by 1H and 13C NMR spectroscopy methods, including the COSY (1H-1H), HMQC (1H-13C) and HMBC (1H-13 ...[more]

PMID: 39125014

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Project description:Much work has been dedicated to the quest to determine the structure-activity relationship in synthetic brassinosteroid (BR) analogs. Recently, it has been reported that analogs with phenyl or benzoate groups in the alkyl chain present activities comparable to those shown by natural BRs, depending on the nature of the substituent in the aromatic ring. However, as it is well known that the activity depends on the structure of the whole molecule, in this work, we have synthesized a series of compounds with the same substituted benzoate in the alkyl chain and a hydroxyl group at C3. The main goal was to compare the activities with analogs with -OH at C2 and C3. Additionally, a molecular-docking study and molecular dynamics simulations were performed to establish a correlation between the experimental and theoretical results. The synthesis of eight new BR analogs was described. All the analogs were fully characterized by spectroscopical methods. The bioactivity of these analogs was assessed using the rice lamina inclination test (RLIT) and the inhibition of the root and hypocotyl elongation of Arabidopsis thaliana. The results of the RLIT indicate that at the lowest tested concentration (1 × 10-8 M), in the BR analogs in which the aromatic ring was substituted at the para position with methoxy, the I and CN substituents were more active than brassinolide (50-72%) and 2-3 times more active than those analogs in which the substituent group was F, Cl or Br atoms. However, at the highest concentrations, brassinolide was the most active compound, and the structure-activity relationship changed. On the other hand, the results of the A. thaliana root sensitivity assay show that brassinolide and the analogs with I and CN as substituents on the benzoyl group were the most active compounds. These results are in line with those obtained via the RLIT. A comparison of these results with those obtained for similar analogs that had a hydroxyl group at C2 indicates the importance of considering the whole structure. The molecular-docking results indicate that all the analogs adopted a brassinolide-like orientation, while the stabilizing effect of the benzoate group on the interactions with the receptor complex provided energy binding values ranging between -10.17 and -13.17 kcal mol-1, where the analog with a nitrile group was the compound that achieved better contact with the amino acids present in the active site.

Dataset Information

Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine.

Publications

Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine.

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