Innovative Piperidine-Catalyzation in Protecting Carbonyl Compounds with Implications for Angiogenesis and Inflammation

Mukhlif Mohsin Slaihim ^1*, Luay Ali Dhahi ¹, Abeer Hussein Ali ¹

Introduced piperidine-catalyzed protection in aldehydes, guiding anti-cancer compound optimization.

Abstract

Introduction: This study explores the application of piperidine-catalyzed protection, an innovative technique, for safeguarding various carbonyl compounds functioning as acetals in a generic reaction. Specifically, we investigate the catalysis of 2-amino-1,3-propanediol-2-methyl with various aromatic aldehydes, leading to the production of cis and trans-5-methyl-2-(mono or di-substitutions-phenyl)-1,3-dioxane-5-amine. Methods: Identification of all newly formed products is achieved through the utilization of spectroscopic techniques, including IR, 1H-NMR, and 13C-NMR spectroscopy. Molecular interactions and potential therapeutic applications of compounds E1 and E2 are demonstrated with cAMP-specific phosphodiesterase (1zkl) and oxidized purine nucleoside triphosphate hydrolase (5ws7). Detailed structural analyses highlight specific hydrogen bonds, pi-pi stacked interactions, and alkyl contacts formed by these compounds with target proteins. A comprehensive bioinformatics approach involves GO enrichment, STRING protein-protein association networks, KEGG pathway analysis, and Reactome pathways to elucidate biological processes, molecular functions, and cellular components associated with the compounds. Results: Compounds E1 and E2 exhibit diverse enrichment profiles, suggesting their involvement in various signaling cascades, neurotransmission, immune responses, and cancer pathways. Comparative analysis of five compound pairs (A1/A2, B1/B2, C1/C2, D1/D2, E1/E2) reveals subtle distinctions in enrichment patterns, implying unique pharmacological advantages for each pair. Conclusion: This study introduces a separate investigation on piperidine-catalyzed protection of carbonyl groups in aldehydes, presenting a practical approach. Emphasizing the significance of understanding distinct biological signatures, our findings guide therapeutic applications and compound optimization, particularly in the context of anti-cancer therapeutics. The compounds show potential in modulating neuronal function, neurotransmission, cancer mechanisms, and immune responses, suggesting promising avenues for future research and development.

Keywords: Carbonyl protection, 1,3-propanediol, 5-methyl-2-(sub-phenyl)-1,3-dioxane-5-amine.

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