SYNTHESIS AND IN SILICO PREDICTION OF THE BIOLOGICAL ACTIVITY, TOXICITY, AND ADME PARAMETERS OF 2-HYDROXY-3-NITROBENZYLIDENE HYDRAZIDE OF α-METHYL-β-(N-MORPHOLYL)PROPANOIC ACID

Received: 16 August 2026

Accepted: 07 October 2026

Published online: 30 October 2026

UDC: 615.322:547.574.3

DOI: 10.53511/pharmkaz.2026.5.22

Article type: Original Research Article

 

SYNTHESIS AND IN SILICO PREDICTION OF THE BIOLOGICAL ACTIVITY, TOXICITY, AND ADME PARAMETERS OF 2-HYDROXY-3-NITROBENZYLIDENE HYDRAZIDE OF
α-METHYL-β-(N-MORPHOLYL)PROPANOIC ACID

 

Dmitry Alexandrovich Berillo¹,
Akzhonas Ermekovna Khamitova²

¹ Manash Kozybayev North Kazakhstan University, Petropavlovsk, Kazakhstan
² Asfendiyarov Kazakh National Medical University, Almaty, Kazakhstan

 

Introduction. This work presents the synthesis of 2-hydroxy-3-nitrobenzylidenehydrazide of α-methyl-β-(N-morpholyl)propionic acid, its HPLC analysis coupled with mass spectrometry, and the computer-based prediction of its biological activity, toxicity, and pharmacokinetic properties.

Objective. To synthesize 2-hydroxy-3-nitrobenzylidenehydrazide of α-methyl-β-(N-morpholyl)propionic acid and evaluate its potential biological activity, toxicity, and pharmacokinetic properties using in silico methods.

Materials and methods. The compound was synthesized by condensation of α-methyl-β-(N-morpholyl)propionic acid hydrazide with 2-hydroxy-3-nitrobenzaldehyde. Identification and purity analysis were performed using HPLC–UV/MS. Biological activity prediction was carried out using PASS Online, toxicity prediction using ProTox-II, and pharmacokinetic parameter assessment using SwissADME.

Results. The synthesis yielded a product containing 2-hydroxy-3-nitrobenzylidene hydrazide of α-methyl-β-(N-morpholyl)propanoic acid with a yield of 65%. Mass spectrometric data confirmed the presence of the target compound in the obtained product. However, according to HPLC-UV analysis, the main chromatographic component accounted for 53.6% of the total area of the detected peaks, indicating the presence of accompanying components in the analyzed sample and the need for further purification.

According to PASS Online predictions, the compound may exhibit antiviral, antitubercular, antimycobacterial, antibacterial, and antiprotozoal activities, as well as the ability to inhibit STAT/STAT3 signaling pathways. According to ProTox-II data, the compound belongs to toxicity class V (LD₅₀ = 3000 mg/kg) and is characterized by the absence of pronounced hepatotoxicity and cytotoxicity. ADME analysis revealed high gastrointestinal absorption, inability to penetrate the blood-brain barrier, and a low probability of drug-drug interactions.

Discussion. The obtained results indicate that 2-hydroxy-3-nitrobenzylidenehydrazide of α-methyl-β-(N-morpholyl)propionic acid is a promising candidate for further pharmacological studies and experimental confirmation of the predicted biological activities in vitro and in vivo.

Conclusions. 2-Hydroxy-3-nitrobenzylidenehydrazide of α-methyl-β-(N-morpholyl)propionic acid was synthesized and characterized for the first time. The results of computer modeling indicate promising biological properties, low toxicity, and a favorable ADME profile, allowing this compound to be considered a promising object for further pharmacological investigations.

Keywords: hydrazones, morpholine, synthesis, biological activity, PASS Online, ProTox-II, SwissADME, in silico modeling.

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